Kyushu University Academic Staff Educational and Research Activities Database
Researcher information (To researchers) Need Help? How to update
Yoshio Hisaeda Last modified date:2021.05.28

Executive Vice President(Senior Vice President) / Biofunctional Chemistry
Trustee(Vice President)


Graduate School
Undergraduate School
Other Organization
Administration Post
Other
Vice President
Other


E-Mail *Since the e-mail address is not displayed in Internet Explorer, please use another web browser:Google Chrome, safari.
Homepage
https://kyushu-u.pure.elsevier.com/en/persons/yoshio-hisaeda
 Reseacher Profiling Tool Kyushu University Pure
http://www.chem.kyushu-u.ac.jp/~yhisaeda/?lang=en
Hisaeda Lab. .
Phone
092-802-2826
Fax
092-802-2827
Academic Degree
Doctor of Engineering
Country of degree conferring institution (Overseas)
No
Field of Specialization
Biofunctional Chemistry, Coordination Chemistry, Electroorganic Chemistry, Photochemistry, Supramolecular Chemistry
ORCID(Open Researcher and Contributor ID)
0000-0001-9196-8006
Total Priod of education and research career in the foreign country
01years00months
Outline Activities
1) Molecular Design of Artificial Vitamin B12 Enzyme

2) Electroorganic Reactions Mediated by Metal Complexes

3) Catalytic Activity of Bis-cobalt coomplexes

4) Catalytic Functions of Porphycene Metal Complexes

5) Molecular recognition and Cayalytic Activity of Arificial Proteins

6)Supramolecular Emitter
Research
Research Interests
  • Supramolecular light emitter
    keyword : Supramolecule, Crystal
    2016.05.
  • Chemistry of porphyrin isomers and their metal complexes
    keyword : porphycene, hemiporphycene, corrole, cobalt complex, iron complex, molybdenum complex
    2003.04・Catalytic functions of cobaltporphycene ・Water-soluble porphycene ant its metal complex ・Preparation of Molybdenumporphycene and its photochemical behavior.
  • New function of bis-cobalt complexes
    keyword : dicobalt complex, dendrimer complex, DNA cleavage, Dimerization catalyst, cyclizatyion catalyst
    2003.04・Formation of dendrimer based on coordination to dicobalt complex ・Dimerization and cyclizatyion catalized by dicobalt complex ・DNA cleavage by dicobalt complex with Co-C bonds.
  • Development of green catalytic system
    keyword : photo reaction, vitamin B12, titanium dioxide, degradation of organic chloride compounds
    2004.03・TiO2-B12 hybrid catalyst ・photochemical dehalogenation ・vitamin B12 like reaction combined with phtosensitizer.
  • Design and catalytic function of artificial enzymes based on supramolecular chemistry
    keyword : supramolecule, vitamin B12, artificial enzyme, cobalt complex, porphyrin
    1985.04・Vesicle-type Vitamin B12 Artificial Enzyme ・Artificial Metalloenzyme using HSA ・Artificial Myoglobin.
Academic Activities
Books
1. Hisashi Shimakoshi, Yoshio Hisaeda, Bioorganometallic B12 as Versatile Catalyst for Green Organic Synthesis, https://doi.org/10.1016/B978-0-12-814197-7.00019-4, Photoelectrochemically Driven Electrosynthesis
H. Shimakoshi, Y. Hisaeda
Modern Electrosynthetic Methods in Organic Chemistry, 1st Edition
Eds. by Frank Marken, Mahito Atobe, CRC Press, Chapter 3, (2018).
ISBN 9781482249163 - CAT# K23712, 2019.03.
2. Hisashi Shimakoshi, Yoshio Hisaeda, Photoelectrochemically Driven Electrosynthesis, CRC Press, Photoelectrochemically Driven Electrosynthesis
H. Shimakoshi, Y. Hisaeda
Modern Electrosynthetic Methods in Organic Chemistry, 1st Edition
Eds. by Frank Marken, Mahito Atobe, CRC Press, Chapter 3, (2018).
ISBN 9781482249163 - CAT# K23712, 2018.09.
3. Yoshio Hisaeda, Hisashi Shimakoshi, Handbook of Porphyrin Science, World Scientific, Bioinspired Catalysts with B12 Enzyme Functions
Y. Hisaeda, H. Shimakoshi
Handbook of Porphyrin Science, Vol. 10
Eds. by K. M. Kadish, K. M. Smith, R. Guilard, World Scientific, 313-370 (2010).
, 2010.09.
4. Development of Bio-inspired catalysts for Degradation of Organic Halide Polutants
Yoshio HISAEDA, Hisashi SHIMAKOSHI
Degradation Technology of Organic Compounds with Various Methods, Chapter 1 Paragraph 14, Information Mechanism, pp.73-86, May, 2007.
5. Dechlorination Reaction Mediated by Vitamin B12 Modified Electrode

The Salt Science Research Foundation, Annual Research Report 2003.
Reports
1. Development of porphyrinoid photosensitizers and their photochemical behavior
Photochemistry. Vol. 41, No. 2, (August 2010)

.
2. Bio-inspired Catalysts Learned from Vitamin B12 Enzyme for Degradation of Environmental Pollutants
Bull. Jpn. Soc. Coord. Chem., 53, 10-21 (2009).
.
3. Photochemical Molecular Transformations Mediated by Vitamin B12-Inspired Catalysts.
Papers
1. T. Ono, K. Ishihama, A. Taema, T. Harada, K. Furusho, M. Hasegawa, Y. Nojima, M. Abe, Y. Hisaeda, Dinuclear Triple-Stranded Helicates Composed of Tetradentate Ligands with Al(III) Chromophores: Optical Resolution and Multi-color Circularly Polarized Luminescence Properties, Angew. Chem. Int. Ed., 60, 2614–2618 (2021)., DOI: 10.1002/ange.202011450, 2021.02.
2. T. Ono, Y. Hisaeda, Vapochromism of Organic Crystals Basedon Macrocyclic Compounds and Inclusion Complexes, Symmetry, 12, 1903 (2020)., DOI: https://doi.org/10.3390/sym12111903, 2020.10.
3. N. Xu, T. Ono, Y. Morita, T. Komatsu, Y. Hisaeda, Rectangular holes in porphyrin isomers act as mono- and bi-nucleating ligands: The first entry of mono- and di-boron porphycenes and their protonation behaviors, Inorg. Chem., 60, 574–583 (2020)., DOI: https://doi.org/10.1021/acs.inorgchem.0c01266, 2020.10.
4. T. Koide, S. Iwamori, S. Koga, Y. Suzuki, J. Kawamata, Y. Hisaeda, Synthesis of 2,6,9-substituted xanthen-3-one and solvent effect on structural and photophysical properties, Dyes and Pigments, 182, 108667 (2020)., DOI: https://doi.org/10.1016/j.dyepig.2020.108667, 2020.09.
5. L. Cui, T. Ono, M. J. Hossain, Y. Hisaeda, Electrochemically Driven, Cobalt–Carbon Bond-Mediated Direct Intramolecular Cyclic and Acyclic Perfluoroalkylation of (Hetero)Arenes using X(CF2)4X, RSC Advances, 10, 24862 - 24866 (2020)., DOI: 10.1039/d0ra05295g, 2020.08.
6. H. Shimakoshi, K. Shichijo, S. Tominaga, Y. Hisaeda, M. Fujitsuka, T. Majima, Catalytic Dehalogenation of Aryl Halides via Excited State Electron Transfer from the Co(I) State of B12 Complex, Chem. Lett., 49, 820-822 (2020)., DOI: https://doi.org/10.1246/cl.200241, 2020.07.
7. L. Cui, T. Ono, Y. Morita, Y. Hisaeda, Electrocatalytic Reactivity of Imine/Oxime-type Cobalt Complex for Direct Perfluoroalkylation of Indole and Aniline Derivatives, Dalton Trans., 49, 7546 - 7551 (2020)., DOI: 10.1039/d0dt01377c, 49, 2020.06.
8. Taro Koide, Takafumi Maeda, Tsukasa Abe, Yoshihito Shiota, Yoshio Yano, Toshikazu Ono, Kazunari Yoshizawa, Yoshio Hisaeda, Mechanistic Study on Ring-Contracting Skeletal Rearrangement from Porphycene to Isocorrole by Experimental and Theoretical Methods, European Journal of Organic Chemistry, 10.1002/ejoc.201901659, 2020, 12, 1811-1816, 2020.03, In this study, the ring contracting skeletal rearrangement reaction in one-pot under basic conditions from octaethylporphycene to two types of isocorroles, i.e., the meso-formyl and meso-free forms, was confirmed and the reaction mechanism was proposed by the comparative analyses of the experimental and theoretical studies. The electron accepting nature of the porphycene and imine-amine conversion of pyrrole rings make it possible to react with hydroxide ions and the following reaction to afford isocorroles. Based on this reaction, the valence of the compound as a ligand as well as the photochemical and electrochemical properties were dramatically changed..
9. Keita Shichijo, Mamoru Fujitsuka, Yoshio Hisaeda, Hisashi Shimakoshi, Visible light-driven photocatalytic duet reaction catalyzed by the B12-rhodium-titanium oxide hybrid catalyst, Journal of Organometallic Chemistry, 10.1016/j.jorganchem.2019.121058, 907, 2020.02, The hybrid catalyst composed of the B12 complex and rhodium ion (Rh3+) modified titanium oxide was synthesized for the visible light-driven B12 inspired catalytic reaction. The hybrid catalyst contains 4.93 × 10−6 molg−1 of the B12 complex and 5.43 × 10−5 molg−1 of the Rh(III) ion on the surface of titanium oxide. Visible light irradiation (λ ≧ 420 nm) of the hybrid catalyst in the presence of triethylamine (Et3N) as a sacrificial reagent showed absorption at 390 nm, typical for the Co(I) state of the B12 complex monitored by diffuse reflectance UV–vis analysis, which imply that electron transfer from the titanium oxide to Co(III) center of the B12 complex occurred by the visible light irradiation. Benzotrichloride was converted to N,N-diethylbenzamide by the visible light irradiation catalyzed by the hybrid catalyst in air at room temperature. Both the conduction band electron and valence band hole of the catalyst were utilized for the reaction to form the amide product. The reaction mechanism of the duet reaction was proposed..
10. Taro Koide, Zihan Zhou, Ning Xu, Yoshio Yano, Toshikazu Ono, Zhongli Luo, Hisashi Shimakoshi, Yoshio Hisaeda, Electrochemical properties and catalytic reactivity of cobalt complexes with redox-active meso -substituted porphycene ligands, Journal of Porphyrins and Phthalocyanines, 10.1142/S1088424619500780, 24, 1-3, 90-97, 2020.01, The cobalt complexes of meso-aryl substituted porphycenes were synthesized and characterized. The reduction potentials of the complexes were shifted to the positive side depending on the strength of the electron-withdrawing properties of the meso-substituents, while the optical properties, such as the absorption spectra of these complexes, were similar. This suggests that the energy levels of the molecular orbitals of the complexes were changed by the meso-substituents while the gaps of the orbitals were not significantly changed. The one-electron reduction of the complex did not afford the Co(I) species, but the ligand-reduced radical anion, which was characterized by electrospectrochemistry. The generated ligand-reduced species reacted with alkyl halides to form the Co(III)-alkyl complex. As a result, the reduction potential of the electrolytic reaction could be directly controlled by the substituents of the porphycene. The catalytic reaction with trichloromethylbenzene was also performed and it was found that the ratio of the obtained products was changed by the reduction potentials of the catalyst, i.e. the cobalt porphycenes..
11. Toshikazu Ono, Hyuga Shinjo, Daiki Koga, Yoshio Hisaeda, Synthesis of a meso-Tetraalkylporphycene Bearing Reactive Sites
Toward Porphycene–Polydimethylsiloxane Hybrids with Enhanced Photophysical Properties, European Journal of Organic Chemistry, 10.1002/ejoc.201901497, 2019, 46, 7578-7583, 2019.12, meso-Tetraalkyl porphycenes exhibit unique optical properties with wide potential applications. The very fact that incorporation of porphycenes into polymeric materials is rare, make this approach a particularly attractive one. In this work, meso-tetrakis(3-butenyl)porphycene bearing four terminal olefin groups is prepared via two synthetic strategies: 1) the McMurry reaction using 5,5′-diacyl-2,2′-bipyrroles as precursors and 2) the oxidative coupling of dipyrroethenes. The newly obtained porphycene has been characterized by single X-ray crystallography. A porphycene–polydimethylsiloxane hybrid film is successfully prepared by a platinum-catalyzed hydrosilylation reaction. The hybrid film can be anchored with tweezers, showing a weak red emission with a quantum yield of 0.4 % at room temperature, whose intensity drastically increases reaching a quantum yield of 6.7 % in liquid nitrogen (77 K). This report represents the first example of porphycene-containing elastomeric films for potential application in various fields..
12. Hui Tian, Hisashi Shimakoshi, Toshikazu Ono, Yoshio Hisaeda, Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B 12 Model Complex under Aerobic Conditions, ChemPlusChem, 10.1002/cplu.201800522, 84, 3, 237-240, 2019.03, A visible light responsive catalytic system with the B 12 complex as the catalyst and [Ir(dtbbpy)(ppy) 2 ]PF 6 as the photosensitizer was developed. It provides a convenient and efficient way to synthesize amides. Based on this method, trichlorinated organic compounds were converted into amides in the presence of an amine under aerobic conditions at room temperature in a one-pot procedure. Various trichlorinated organic compounds and an amine source, such as primary, secondary, and cyclic amines, have been evaluated for this transformation, providing the expected products in moderate to excellent yields. Notably, product formation depended on the reaction atmosphere where the amide was obtained under aerobic conditions while partially dechlorinated products were obtained under anaerobic conditions. As this protocol is free from hazardous reagents, extra additives, noble metals, and dangerous gas, the present method provides a novel and efficient approach for amide synthesis under mild and easily controlled conditions..
13. Toshikazu Ono, Yoshio Hisaeda, Flexible-color tuning and white-light emission in three-, four-, and five-component host/guest co-crystals by charge-transfer emissions as well as effective energy transfers, Journal of Materials Chemistry C, 10.1039/c8tc06165c, 7, 10, 2829-2842, 2019.01, Three-, four-, and five-component host/guest crystals with multi-color and white light emission is described. Our strategy is based on the confinement of aromatic donor guests in supramolecular acceptor hosts. The supramolecular acceptor hosts (NDI-TPFB) were composed of N,N′-dipyrid-3-yl-1,4,5,8-naphthalenediimide (NDI) with two tris(pentafluorophenyl)borane (TPFB) linked by boron-nitrogen dative bonds as Lewis acid-base pairs, which spontaneously formed upon mixing the components. In the first part, a set of three-component crystals with 14 different aromatic guests were characterized to elucidate the structure-property relationships. In the latter part, a series of 17 types of four- and five-component crystals were formed with the use of binary or ternary guest inclusion systems, and their structural and photophysical properties were investigated. Among them, 14 types of crystals were formed effectively without destroying the crystal structure, as determined by X-ray diffraction and fluorescence microscopy. Notably, flexible color tuning, including white light emission, was realized by tuning the guest ratio and the combinations. Various intermolecular interactions such as C-H⋯F interactions, π-π stacking, charge-transfer interactions, and inclusion phenomena were important for forming the crystals. This approach that yields a rational solution of multicomponent crystals could be potentially useful for obtaining novel photofunctional solid-state systems..
14. Md Jakir Hossain, Toshikazu Ono, Yoshio Yano, Yoshio Hisaeda, Learning From Vitamin B
12
-Mediated Reactions
Cobalt(III)−Carbon-Assisted Catalytic C−H Difluoroacylation of (Hetero)Arenes through Controlled-Potential Electrolysis, ChemElectroChem, 10.1002/celc.201900164, 2019.01, The synthesis of difluoromethylated (CF
2
R) (R=H, alkyl/aryl, CO
2
R, etc.) compounds has received considerable attention in recent years. In this study, the cobalt(III)−carbon-mediated catalytic C−H difluoroacylation of unactivated arenes and heteroarenes using BrCF
2
CO
2
Et is reported. This catalytic cycle is based on a valence change of the cobalt catalyst, a naturally derived vitamin B
12
derivative, driven by controlled-potential electrolysis at −0.8 V vs. Ag/AgCl under visible-light irradiation in dimethyl sulfoxide. A broad substrate scope is demonstrated, and two compounds were characterized according to their X-ray crystal structures. Mechanistic studies showed that the reaction proceeds through a radical pathway mediated by homolytic cleavage of the cobalt(III)–carbon bond. A turnover number of more than 100 was observed, owing to the inherent stability of the vitamin B
12
framework. This naturally derived catalytic system has potential applications in medicinal chemistry and materials science..
15. Koichi Hashimoto, Taro Koide, Toru Okawara, Hisashi Shimakoshi, Yuta Hori, Yoshihito Shiota, Kazunari Yoshizawa, Yoshio Hisaeda, Redox behaviour of the β-dihydroporphycene cobalt complex
study on the effect of hydrogenation of the ligand, Dalton Transactions, 10.1039/c8dt03743d, 48, 3, 872-881, 2019.01, The dihydrogenated porphycene cobalt(ii) complex was synthesized and electrochemical experiments were carried out. The one-electron reduction of the complex proceeded at the central metal to afford the Co(i) species; in contrast, for the non-hydrogenated porphycene cobalt(ii) complex, the one-electron reduction gave the ligand reduced radical anion species. The reactivity of the one-electron reduced species with alkyl halides showed clear differences between the complexes. Hydrogenation of the β-position of the porphycene makes it possible to generate a central cobalt reduced species possessing a higher reactivity than the ligand reduced radical anion species..
16. Toshikazu Ono, Y. Tsukiyama, A. Taema, Yoshio Hisaeda, Inclusion Crystal Growth and Optical Properties of Organic Charge-transfer Complexes Built from Small Aromatic Guest Molecules and Naphthalenediimide Derivatives, Chem. Lett., 46, No.6, 801-804 (2017)., 10.1246/cl.161019, 2017.03.
17. Hisashi Shimakoshi, Z. Luo, K. Tomita, Yoshio Hisaeda, Cathodic Reductive Couplings and Hydrogenations of Alkenes and Alkynes Catalyzed by the B12 Model Complex, J. Organometal. Chem., 839, 71-77 (2017)., http://doi.org/10.1016/j.jorganchem.2017.02.002, 2017.02.
18. Hisashi Shimakoshi, Yoshio Hisaeda, Hybrid Catalyst for Light-Driven Green Molecular Transformations, ChemPlusChem, 82, No.1, 18-29 (2017). (Back Cover), 10.1002/cplu.201600303, 2017.01.
19. Toshikazu Ono, Daiki Koga, Yoshio Hisaeda, Facile Synthesis of 9,10,19,20-Tetraalkylporphycenes, Chem. Lett., 46, No.2, 260-262 (2017)., 10.1246/cl.161019, 2017.01.
20. Sou Hatanaka, Toshikazu Ono, Yoshio Hisaeda, Turn-on Fluorogenic and Chromogenic Detection of Small Aromatic Hydrocarbon Vapors by a Porous Supramolecular Host, Chem. Eur. J., 22, No.30, 10346 –10350 (2016)., 10.1002/chem.201601812, 2016.08.
21. Hisashi Shimakoshi, Zhongli Luo, Yoshio Hisaeda, Electrolysis of Trichloromethylated Organic Compounds under Aerobic Conditions Catalyzed by B12 Model Complex for Ester and Amide Formations, Dalton Trans., 45, No.25, 10173-10180 (2016). (Back Cover), 10.1039/c6dt00556j, 2016.06.
22. M. Giedyk, Hisashi Shimakoshi, D. Gryko, Yoshio Hisaeda, Electrochemistry and Catalytic Properties of Amphiphilic Vitamin B12 Derivatives in Nonaqueous Media, Dalton Trans., 45, No.20, 8340-8346 (2016). (Inside Front Cover), 10.1039/c6dt00355a, 2016.05.
23. Yoshitsugu Morita, Koji Oohora, Akiyoshi Sawada, Kazuki Doitomi, Jun Ohbayashi, Takashi Kamachi, Yoshizawa Kazunari, Yoshio Hisaeda, Takashi Hayashi, Intraprotein transmethylation via a CH3–Co(III) species in myoglobin reconstituted with a cobalt corrinoid complex, Dalton Trans., 45, No.8, 3277-3284 (2016). (Front Cover), 10.1039/c5dt04109k, 2016.04.
24. Yoshio Hisaeda, Hisashi Shimakoshi, Kazumasa Noda, Tetsuro Majima, Bioinspired Catalytic Reactions with Vitamin B12 Derivative and Photosensitizers, Pure. Appl. Chem.,, DOI: 10.1351/PAC-CON-12-10-05, 2013.04, As part of a study directed toward design of good catalytic systems based upon a
hydrophobic vitamin B12, heptamethyl cobyrinate perchlorate, we describe the preparation of
various nanomaterials using the vitamin B12 derivative and photosensitizers. Examples
include vitamin B12-hyperbranched polymers (HBPs), human serum albumin (HSA) containing
vitamin B12 derivatives, a vitamin B12-titanium dioxide hybrid catalyst, a vitamin
B12-Ru complex combined system, and a vitamin B12-rose bengal combined system. These
bioinspired materials have the potential as catalytic systems for the degradation of organic
halide pollutants and for molecular transformations via radical intermediates during irradiation
by UV or visible light, and offer a variety of applications that are of great interest in
terms of green chemistry..
25. Yoshio Hisaeda, Hisashi Shimakoshi, Kazumasa Noda, Tetsuro Majima, Metallopolymer Films Exhibiting Three-color Electrochromism in the UV/Vis and Near-IR Region: Remarkable Utility of Trimetallic Clusters Bearing Thienyl Pendants and Their Mixed-valent Charge Transfer Transitions, Journal of Inorganic and Organometallic Polymers and Materials, DOI: 10.1007/s10904-012-9758-9, 2013.04, ANovel oxo-centered, acetate-bridged trinuclear
ruthenium clusters functionalized with two pyridine ligands
with thienyl substituents, [Ru3O(CH3COO)6(CO)(L1)2]
(1) and [Ru3O(CH3COO)6(CO)(L2)2] (2), where L1 =
4-(2-thienyl)pyridine and L2 = 4-(2,20-bithienyl)pyridine,
have been synthesized and characterized. The molecular
structure of 2 has been determined by single-crystal X-ray
diffraction. One-electron oxidation of 2 with silver(I) cation
has led to the isolation of a CO-dissociated product,
[Ru3O(CH3COO)6(H2O)(L2)2]PF6 (3!PF6), and subsequent
reaction with 4-dimethylaminopyridine (dmap) gave
[Ru3O(CH3COO)6(dmap)(L2)2]PF6 (4!PF6). Linear metallopolymers
containing the {Ru3O(CH3COO)6} groups have
been deposited onto indium-tin oxide surface via oxidative
electropolymerization of 2, 3!PF6, and 4!PF6. These metallopolymer
thin films exhibit three-color electrochromism
in the UV/Vis and near-IR region associated with the
Ru3
II,III,III, Ru3
III,III,III, and Ru3
III,III,IV oxidation states..
26. Yoshio Hisaeda, Keishiro Tahara, Kumiko Mikuriya, Takahiro Masuko, Junichi kikuchi, Dechlorination of DDT catalyzed by visible-light-driven system composed of vitamin B12 derivative and Rhodamine B, J. Porphyrins Phthalocyanines, 17, No. 01n02, 135-141 (2013)., DOI: 10.1142/S1088424612501398, 2013.03, The visible-light-driven dechlorination of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane
(DDT) was carried out in the presence of a hydrophobic vitamin B12, heptamethyl cobyrinate
perchlorate and Rhodamine B. DDT was successfully dechlorinated to form 1,1-bis(4-chlorophenyl)-
2,2-dichloroethane (DDD) as the mono-dechlorinated product upon visible light irradiation with a
tungsten lamp (l > 440 nm). Upon prolonged visible light irradiation to DDT, DDMU (1-chloro-2,2-
bis(4-chlorophenyl)ethylene), DDMS (1-chloro-2,2-bis(4-chlorophenyl)ethane) and DCS (trans-4,4′-
dichlorostilbene) were obtained as the di- and tri-dechlorinated products. The use of the photostable
organic sensitizer enabled prolonged photocatalysis via a noble-metal-free process. The vitamin B12
derivative was replaced by an imine/oxime-type cobalt complex although the cobalt complex system
showed a lower catalytic activity than the B12 derivative system. The dechlorination mechanism in the
B12-Rhodamin B system was investigated by various methods such as UV-vis absorption and fluorescence
quenching.
.
27. Yoshio Hisaeda, Keishiro Tahara, Ayaka Matsuzaki, Yoshio Hisaeda, Synthesis, Characterization, Co-S Bond Reactivity of a Vitamin B12 Model Complex Having Pentafluorophenylthiolate as an Axial Ligand, Dalton Trans., 42, No.18, 6410-6416 (2013)., DOI: 10.1039/C3DT00042G, 2013.03, Heptamethyl (aquo)(pentafluorophenylthiolate)cobyrinate perchlorate, [(H2O)(C6F5S)Cob(III)7C1ester]-
ClO4, was synthesized as a B12 model complex having a thiolate ligand in the axial position. The axial
ligand change in heptamethyl (diaquo)cobyrinate diperchlorate, [(H2O)2Cob(III)7C1ester](ClO4)2, from
H2O to C6F5S− afforded the B12–thiolate complex. The B12–thiolate model complex was characterized by
UV-vis, NMR and ESI-mass spectroscopies. The coordination of C6F5S− to the cobalt center affected the
spectroscopic properties of the corrin ring through the electronic interaction between the axial ligand
(C6F5S−) and the equatorial ligand (corrin). The photolysis of the B12–thiolate model complex led to the
homolytic cleavage of the Co(III)–S bond to form the Co(II) complex and the phenyl thiyl radical. The
thermolysis of the B12–thiolate model complex also led to the homolytic cleavage of the Co(III)–S bond.
Furthermore, the reactivity of the Co(III)–S bond of the B12–thiolate model complex was applied to the
catalytic oxidation of C6F5SH to C6F5S–SC6F5..
28. Yoshio Hisaeda, Hisashi Shimakoshi, Kazumasa Noda, Tetsuro Majima, Photoinduced Electron Transfer in Supramolecular Donor-Acceptor dyad of Zn Corrphycene, Phys. Chem. Chem. Phys., 15, No.15, 5677-5683 (2013)., DOI: 10.1039/c3cp43795g, 2013.03, Porphyrins have been used by various researchers as important building blocks of photofunctional
molecules, while the number of studies on the excitation properties of the structural isomers of
porphyrins is small when compared to those of porphyrins. In the present study, photoinduced electron
transfer (ET) processes of supramolecular donor–acceptor dyads of 2,3,6,7,11,12,17,18-
octaethylcorrphycenatozinc (ZnCn), one of the porphyrin isomers, and some imide compounds, which
can coordinate to the central Zn ion as an electron acceptor, were investigated. Formation of the
supramolecular donor–acceptor dyads was confirmed by steady state absorption change. Charge
separation and charge recombination processes upon photoexcitation of ZnCn of the supramolecular
dyads were successfully observed by subpicosecond laser flash photolysis. The estimated ET rates (kET)
were compared with those of other porphyrin isomers. Differences in the driving force dependence of
kET values of porphyrin isomers were attributed to the electronic coupling and internal reorganization
energy. Electronic and structural factors, which brought about the difference in kET values, were
reasonably explained on the basis of the theoretical calculation..
29. T. Okawara, M. Abe, H. Shimakoshi, Y. Hisaeda, A Pd(II)-hydroxyporphycene: synthesis, characterization, and photoinduced proton-coupled electron transfer, Res. Chem. Intermed., DOI: 10.1007/s11164-012-0640-8, 2012.10, A Pd(II) complex, Pd(TPrPc-OH) (1, TPrPc-OH = 9-hydroxy-2,7,12,17-tetrapropylporphycenato dianion), has been synthesized and characterized. 1H NMR spectroscopy revealed that compound 1 exists as its enol form in solution. The H atom of the hydroxy group in 1 was exchanged with deuterium on addition of ethanol-d6. UV–visible spectra showed a red shift of theQband of 1 in THF compared with that of
the acetoxy derivative Pd(TPrPc-OAc) (2, TPrPc-OAc = 9-acetoxy-2,7,12,17-tetrapropylporphycenato dianion). The pKa value of the hydroxy group in 1 was determined, by means of a UV–visible titration experiment, to be 10.56. A cyclic voltammogram of 1 in a mixture of THF and Britton–Robinson buffered aqueous solution revealed one-electron and one-proton coupled transfer in the oxidation process
in the pH range from 2.7 to 10.5, which was identified by pH-varying experiments and the Pourbaix diagram. Transient absorption spectroscopy revealed that an electron-transfer reaction occurred from the triplet excited-state of 1 to 2,3,5,6-tetramethyl-1,4-benzoquinone (duroquinone, DQ) upon pulse laser irradiation at 532 nm. Such an intermolecular photoinduced electron-transfer reaction was not observed
between the Ni analog, Ni(TPrPc-OH), and DQ. The reaction rate constant, kq, was indicative of a kinetic isotope effect with kq(H)/kq(D) = 1.7, supporting the belief that the exited-state electron transfer from 1 to DQ is accompanied by proton transfer..
30. R. Matsuse, M. Abe, Y. Tomiyasu, A. Inatomi, H. Yonemura, S. Yamada, Y. Hisaeda, Metallopolymer Films Exhibiting Three-color Electrochromism in the UV/Vis and Near-IR Region: Remarkable Utility of Trimetallic Clusters Bearing Thienyl Pendants and Their Mixed-valent Charge Transfer Transitions, Journal of Inorganic and Organometallic Polymers and Materials, DOI: 10.1007/s10904-012-9758-9, 2012.10, Novel oxo-centered, acetate-bridged trinuclear ruthenium clusters functionalized with two pyridine ligands with thienyl substituents, [Ru3O(CH3COO)6(CO)(L1)2] (1) and [Ru3O(CH3COO)6(CO)(L2)2] (2), where L1 = 4-(2-thienyl)pyridine and L2 = 4-(2,20-bithienyl)pyridine,
have been synthesized and characterized. The molecular structure of 2 has been determined by single-crystal X-ray diffraction. One-electron oxidation of 2 with silver(I) cation has led to the isolation of a CO-dissociated product, [Ru3O(CH3COO)6(H2O)(L2)2]PF6 (3!PF6), and subsequent reaction with 4-dimethylaminopyridine (dmap) gave [Ru3O(CH3COO)6(dmap)(L2)2]PF6 (4!PF6). Linear metallopolymers containing the {Ru3O(CH3COO)6} groups have been deposited onto indium-tin oxide surface via oxidative electropolymerization of 2, 3!PF6, and 4!PF6. These metallopolymer thin films exhibit three-color electrochromism in the UV/Vis and near-IR region associated with the Ru3 II,III,III, Ru3 III,III,III, and Ru3 III,III,IV oxidation states..
31. Yoshio Hisaeda, Masaaki Abe, Atsushi Inatomi, Oxo-centered Trimetallic Clusters Supported by Electron-withdrawing Carboxylates: Highly Inert Character in Ligand Exchange Kinetics of Dichloroacetate-bridged Complex [Ru3(μ3-O)(μ-CHCl2COO)6(pyridine)3], Aust. J. Chem., No.65, 1599-1607 (2012)., http://dx.doi.org/10.1071/CH12378, 2012.10, Two new oxo-centred trinuclear ruthenium clusters supported by six dichloroacetate ligands, [Ru3(m3-O)(m-CHCl2COO)6
(CH3OH)3]CHCl2COO (1) and [Ru3(m3-O)(m-CHCl2COO)6(pyridine)3] (2), have been synthesised and characterised by
spectroscopic methods, electrospray ionisation mass spectrometry, single-crystal X-ray diffraction, and cyclic voltammetry.
Due to the strong inductive effect of the dichloroacetate ligands, the redox potential of 2 was shifted to the positive
side (,1.0V or more) relative to the acetate analogue [Ru3(m3-O)(m-CH3COO)6(pyridine)3], and also the rate of pyridine/
pyridine-d5 exchange reaction of 2 in CD3CN was retarded with the rate constant of kex
298K¼1.910
8 s
1 which is
105-fold smaller than the value for [Ru3(m3-O)(m-CH3COO)6(pyridine)3]. Highly positive activation parameters obtained
for 2, DH
z¼1387 kJ mol
1 and DS
z¼7120 JK
1 mol
1, illustrate a dissociative activation pathway in which
rupture of the Ru–N(pyridine) bond is involved in the rate-determining step..
32. H. Shimakoshi, K. Sasaki, Y. Iseki, Y. Hisaeda, Synthesis and photosensitizing properties of porphycene with imidazolium tag, J. Porphyrins Phthalocyanines, 16, 530-536 (2012)., DOI: 10.1142/S1088424612500551, 16, 530-536, 2012.07, Porphycene having an imidazolium cation tag was synthesized and characterized by elemental analysis, UV-vis, NMR and ESI-mass spectroscopies. This porphycene derivative easily dissolves in various ionic liquids and produces singlet oxygen under irradiation by visible light (λ ≥460 nm). The photophysical parameters of the porphycene in ionic liquids were determined and the values were compared to those in acetonitrile. Photosensitizing reactions using this new porphycene for the oxidation of 1,5-dihydroxynaphthalene in ionic liquids were investigated and found to form 5-hydroxy-1,4-naphthoquinone. The recycled use of the porphycene was efficiently achieved in N,N,Ntrimethyl-
N-propylammonium bis(trifluoromethanesulfonyl)amide ([TMPA][TFSA]) and N-methyl-Npropylpiperidinium bis(trifluoromethanesulfonyl)amide ([P13][TFSA])..
33. T. Okawara, K. Hashimoto, M. Abe, H. Shimakoshi, Y. Hisaeda, Hydrogenation effects in metalloporphycenes: synthesis and redox behavior of Ni(II)–tetra(n-propyl)dihydroporphycene, Chem. Commun. (Inside Front Cover), DOI:10.1039/C2CC30991B, 48, 44, 5413-5415, 2012.06, 生体関連色素であるポルフィリンの構造異性体であるポルフィセンの金属錯体は、金属の還元より配位子の還元が優先して起こるという性質をもつ。本研究では、ポルフィセン配位子の還元により、中心金属の還元が可能になることを示した成果であり、触媒反応への応用が期待できる。
2,3-Dihydro-2,7,12,17-tetrapropylporphycene (1) and its NiII complex (2) have been synthesized and characterized. One-electron reduction of 2 gives a mixture of “ring-reduced” and “metal-reduced” monoanionic species, in which the latter is a prerequisite for electrocatalytic dehalogenation of organic halides..
34. H. Shimakoshi, L. Li, M. Nishi, Y. Hisaeda, Photosensitizing catalysis of B12 complex without additional photosensitizer, Chem. Commun. (Back Cover), 47, 39, 10921-10923, 2011.09, ビタミンB12が光増感作用を示すことを世界で初めて発見しました。従来は光増感剤共存下で進行していた光駆動型ビタミンB12反応を、ビタミンB12単独で進行させることに成功し、環境汚染物質であるDDTの脱塩素化反応応用しました。英国王立化学会Chem. Commun.誌のBack coverを飾りました。

  A cobalamin derivative, heptamethyl cobrinate perchlorate, was activated by UV light irradiation to form a Co(I) species in the presence of triethanolamine and used for a dechlorination reaction, and this photochemical reaction was accelerated in an ionic liquid..
35. T. Okawara, M. Abe, H. Shimakoshi, Y. Hisaeda, Hydroxy-Functionalized Porphycenes: Structure, Spectroscopy, and Electrochemistry, Bull. Chem. Soc. Jpn.(Selected Paper), 84, 7, 718-728, 2011.07.
36. H. Shimakoshi, M. Nishi, A. Tanaka, K. Chikama, Y. Hisaeda, Photocatalytic function of polymer-supported B12 complex with ruthenium trisbipyridine photosensitizer, Chem. Commun.(Inside Front Cover), 47, 23, 6548-6550, 2011.05, 可視光増感作用を示すルテニウム錯体と天然酵素のモデル化合物であるビタミンB12を共重合させたハイブリッドポリマーを作製しました。本ポリマーに可視光照射することで、高効率なポリマー内電子移動が起こり、ビタミンB12触媒反応を行うことが出来ました。

  The hybrid polymer was synthesized by a radical polymerization of a B12 derivative and a Ru complex having styrene moieties in each peripheral position, and the hybrid polymer showed photocatalytic activity for molecular transformation with visible light irradiation..
37. H. Shimakoshi, D. Maeda, Y. Hisaeda, Supramolecular Assemblies of Crown-substituted Dinickel and Dicobalt Complexes with Guest Cation Binding, Supramol. Chem., 23, 1-2, 131-139, 2011.04.
38. K. Tahara, Y. Hisaeda, Eco-friendly Molecular Transformations Catalyzed by Vitamin B12 Derivative with Visible-Light-Driven System, Green Chem., 13, 3, 558-561, 2011.04.
39. L. Pan, K. Tahara, T. Masuko, Y. Hisaeda, Methyl-transfer Reaction to Alkylthiol Catalyzed by a Simple Vitamin B12 Model Complex Using Zinc Powder, Inorg. Chim. Acta, 368, 1, 194-199, 2011.03.
40. K. Tahara, Y. Chen, L. Pan, T. Masuko, H. Shimakoshi, Y. Hisaeda, Electrochemical Catalytic Carbon-Skeleton Rearrangement Reaction Mediated by Imine/Oxime-Type B12 Model Complex, Chem. Lett.(Editor’s Choice), 40, 2, 177-179, 2011.02.
41. H. Shimakoshi, M. Abiru, K. Kuroiwa, N. Kimizuka, M. Watanabe, Y. Hisaeda, Preparation and Reactivity of B12-TiO2 Hybrid Catalyst Immobilized on Glass Plate, Bull. Chem. Soc. Jpn, 82, 2, 170-172, 82, No.2, pp.170-172 (2010), 2010.09.
42. K. Tahara, H. Shimakoshi, A. Tanaka, Y. Hisaeda, Synthesis, Characterization and Catalytic Function of B12-Hyperbranched Polymer, Dalton Trans, 39, 12, 3035-3042, 39, No.12, pp.3035-3042 (2010), 2010.09.
43. S. Izumi, H. Shimakoshi, M. Abe, Y. Hisaeda, Photo-Induced Ring-Expansion Reactions Mediated by B12-TiO2 Hybrid Catalyst, Dalton Trans, 39, 13, 3302-3307, 39, No.13, pp.3302-3307 (2010), 2010.09.
44. D. Maeda, H. Shimakoshi, M. Abe, M. Fujitsuka, T. Majima, Y. Hisaeda, Synthesis of a novel Sn(IV) porphycene-ferrocene triad linked by axial coordination and solvent polarity effect in photoinduced charge separation process, Inorg. Chem, 49, 6, 2872-2880, 49, No.6, pp.2872-2880 (2010), 2010.09.
45. M. Taneda, D. Maeda, H. Shimakoshi, M. Abe, Y. Hisaeda, Preparations and Photosensitizing Properties of 2,7,12,17-Tetra-n-Propylporphycenatotin(IV) Dihalide Complexes, Bull. Chem. Soc. Jpn, 82, 6, 667-671, 82, No.6, pp.667-671 (2010), 2010.09.
46. K. Tahara, H. Shimakoshi, A. Tanaka, Y. Hisaeda, Redox Behavior and Electrochemical Catalytic Function of B12-Hyperbranched Polymer, Bull. Chem. Soc. (BCSJ Award Article), 83, 12, 1439-1446, 83, No.12, pp.1439-1446 2010 (BCSJ Award Article), 2010.09, 近年、脱塩素化反応を行う菌体にビタミンB12が含まれていることが明らかとなり、脱塩素化触媒としての応用が期待されています。本研究では、機能性粒子ハイパーブランチポリマー(HBP)に着目し、これにビタミンB12誘導体を結合したB12修飾ハイパーブランチポリマー(B12-HBP)を創製し、電気化学的手法による脱塩素化反応に成功しました。柔軟な分岐骨格に沿って固定化されたB12部位は、基質や電極に対して高いアクセス性を保持し、B12-HBPは均一系触媒として優れた性質を示しました。土壌残留性農薬DDTの電気化学的脱塩素化反応に成功し、B12-HBPが環境浄化触媒として有効であることを示しました。本論文が、Bull.Chem.Soc.Jpn. BCSJ Award Articleに選ばれ、2010年12月号の表紙に掲載されました。

  The redox behavior of a covalently functionalized hyperbranched polymer with a vitamin B12 derivative (B12-HBP) was investigated by cyclic voltammetry and UV-vis spectroscopy combined with bulk electrolysis in DMF. The B12-HBP showed excellent properties for a homogeneous catalyst such as the good accessibilities of the cobalt centers in B12-HBP to an electrode and substrates and the maintained supernucleophilicity of the Co(I) species to alkyl halides. Furthermore, B12-HBP was used as an electrochemical degradation catalyst for DDT. This work presents the first electrocatalysis study of a catalytically active transition metal complex on a homogeneous dendritic support and investigates the suitability of the present B12-HBP system for electrochemical dehalogenation..
47. M. Taneda, D. Maeda, H. Shimakoshi, M. Abe, Y. Hisaeda, Preparations and Photosensitizing Properties of 2,7,12,17-Tetra-n-Propylporphycenatotin(IV) Dihalide Complexes, Bull. Chem. Soc. Jpn., 82, 6, 667-671, 82, No.6, 667-671 (2010), 2010.06.
48. A. Ikegami, M. Abe, A. Inatomi, Y. Hisaeda, Synthetic Design of Heterometallic Cluster Compounds with Site-Selective and Stepwise Substitution of Bridging Carboxylates, Chem. Eur. J., 16, 15, 4438-4441, 16, No.15, 4438-4441 (2010), 2010.05.
49. S. Izumi, H. Shimakoshi, M. Abe, Y. Hisaeda, Photo-Induced Ring-Expansion Reactions Mediated by B12-TiO2 Hybrid Catalyst, Dalton Trans, 39, 13, 3302-3307, 39, No.13, 3302-3307 (2010), 2010.04.
50. D. Maeda, H. Shimakoshi, M. Abe, M. Fujitsuka, T. Majima, Y. Hisaeda, Synthesis of a novel Sn(IV) porphycene-ferrocene triad linked by axial coordination and solvent polarity effect in photoinduced charge separation process, Inorg. Chem., 49, 6, 2872-2880, 49, No.6, 2872-2880 (2010), 2010.04.
51. K. Tahara, H. Shimakoshi, A. Tanaka, Y. Hisaeda, Synthesis, Characterization and Catalytic Function of B12-Hyperbranched Polymer, Dalton Trans., 39, 12, 3035-3042, 39, No.12, 3035-3042 (2010), 2010.03.
52. H. Shimakoshi, M. Abiru, K. Kuroiwa, N. Kimizuka, M. Watanabe, Y. Hisaeda, Preparation and Reactivity of B12-TiO2 Hybrid Catalyst Immobilized on Glass Plate, Bull. Chem. Soc. Jpn., 82, 2, 170-172, 82, No.2, 170-172 (2010), 2010.02.
53. H. Shimakoshi, M. Nishi, A. Tanaka, K. Chikama, Y. Hisaeda, Synthesis and Catalysis of B12-core-shell-Hyperbranched Polymer, Chem. Lett., 39, 1, 22-23, 39, No.1, 22-23 (2010), 2010.01.
54. Ling PAN, Hisashi SHIMAKOSHI, Takahiro MASUKO, Yoshio HISAEDA, Vitamin B12 Model Complex Catalyzed Methyl Transfer Reaction to Alkylthiol under Electrochemical Conditions with Sacrificial Electrode, Dalton Trans., 44, 9898-9905, Vol.44,9898-9905 (2009), 2009.11.
55. H. Shimakoshi, T. Baba, Y. Izeki, A. Endo, C. Adachi, M. Watanabe, Y. Hisaeda, Photosensitizing Properties of the Porphycene Immobilized in Sol-Gel Derived Silica Coating Films
, Tetrahedron Lett., Vol. 49, No.49, 6198-6201 (2008), 2009.10.
56. H. Shimakoshi, E. Sakumori, Kenji Kaneko, Y. Hisaeda, B12-TiO2 Hybrid Catalyst for Dehalogenation of Organic Halides, Chem. Lett., Vol. 38, No.5, 468-469 (2009), 2009.05.
57. H. Shimakoshi, K. Shibata, Y. Hisaeda, Molecular Recognition of Redox-Switchable Bis-crowns Moieties Assembled on Dicobalt Complex, Inorg. Chem., 48, No.3, 1045-1052 (2009), 2009.03.
58. K. Nakamura, Y. Hisaeda, L. Pan, H. Yamauchi, Methyl Transfer from a Hydrophobic Vitamin B12 Derivative to ArsenicTrioxide, J. Organometal. Chem., No.694, 916 - 921 (2009), 2009.03.
59. D. Maeda, H. Shimakoshi, M. Abe, Y. Hisaeda, Synthesis and Photochemical Property of a New Molybdenum Porphycene Complex, Dalton Trans., No.1, 140-145 (2009), 2009.01.
60. L. Pan, H. Shimakoshi, Y. Hisaeda, Electrochemical Methyl-transfer Reaction to Alkylthiol Catalyzed by Hydrophobic Vitamin B12, Chem. Lett., No.1, 26-27 (2009), 2009.01.
61. K. Nakamura, Y. Hisaeda, L. Pan, H. Yamauchi, Detoxification system for inorganic arsenic: transformation of arsenic trioxide into trimethylarsine oxide (TMAO) by vitamin B12 derivatives and conversion of TMAO into arsenobetaine, Chem. Commun., No.41, 5122 - 5124 (2008), 2008.10.
62. H. Shimakoshi, T. Baba, Y. Iseki, I. Aritome, A. Endo, C. Adachi, Y. Hisaeda, Photophysical and Photosensitizing Properties of Brominated Porphycenes, Chem. Commun., No.25, 2882-2884 , 2008.03.
63. Md. Abdul JABBAR, Hisashi SHIMAKOSHI, Yoshio HISAEDA, Enhanced Reactivity of Hydrophobic Vitamin B12 towards the Dechlorination of DDT in Ionic Liquid, Chem. Commun., pp.1653-1655, 2007.04.
64. Daisuke MAEDA, Isao ARITOME, Hisashi SHIMAKOSHI and Yoshio HISAEDA, Oxo(2,3,6,7,12,13,16,17-octaethylporphycenato) molybdenum(V) hexamolybdate, Acta Cryst.E, Vol.E62, pp.m1272-m1274, 2006.05.
65. H. Shimakoshi, Y. Maeyama, T. Kaieda, T. Matsuo, E. Matsui, Y. Naruta, Y. Hisaeda, Hydrophobic Vitamin B12 Part 20: Supernucleophilicity of Co(I) Heptamethyl Cobyrinate toward Various Organic Halides, Bull. Chem. Soc. Jpn., 10.1246/bcsj.78.859, 78, 5, 859-863, Vol.78, No.5, 859-863, 2005.05.
66. H. Shimakoshi, H. Takemoto, I. Aritome, Y. Hisaeda, Redox Switchable Molecular Containers Consisting of Dicobalt Complexes, Inorg. Chem., 10.1021/ic051482o, 44, 25, 9134-9136, 44, No.25, 9134-9136, 2005.01.
67. H. Shimakoshi, M. Tokunaga, Y. Hisaeda, Hydrophobic Vitamin B12. Part 19. Electroorganic reaction of DDT mediated by hydrophobic vitamin B12, Dalton Trans., 10.1039/b315170k, 6, 878-882, 878-882, 2004.03.
68. H. Sato, T. Hayashi, T. Ando, Y. Hisaeda, T. Ueno, Y. Watanabe, Hybridization of Modified-Heme Reconstitution and Distal Histidine Mutation to Functionalize Sperm Whale Myoglobin, J. Am. Chem. Soc., 10.1021/ja038798k, 126, 2, 436-437, Vol.126, No.2, 436-437, 2004.01.
69. H. Shimakoshi, M. Tokunaga, K. Kuroiwa, N. Kimizuka, Y. Hisaeda, Preparation and electrochemical behaviour of hydrophobic vitamin B12 covalently immobilized onto platinum electrode, Chem. Commun., 10.1039/b309457j, 1, 50-51, 50-51, 2004.01.
70. T. Hayashi, Y. Nakashima, K. Ito, T. Ikegami, I. Aritome, K. Aoyagi, T. Ando, Y. Hisaeda, Synthesis, Characterization and Autoreduction of a Highly Electron-Deficient Porphycenatoiron(III) with Trifluoromethyl Substituents, Inorg. Chem., 10.1021/ic034757d, 42, 23, 7345-7347, Vol.42, No. 23, 7345-7347, 2003.11.
71. T. Hayashi, Y. Nakashima, K. Ito, T. Ikegami, I. Aritome, K. Aoyagi, T. Ando, Y. Hisaeda, Synthesis, Characterization and Autoreduction of a Highly Electron-Deficient Porphycenatoiron(III) with Trifluoromethyl Substituents, Inorg. Chem., 10.1021/ic034757d, 42, 23, 7345-7347, Vol.42, No. 23, 7345-7347, 2003.11.
72. T. Hayashi, Y. Nakashima, K. Ito, T. Ikegami, I. Aritome, A. Suzuki, Y. Hisaeda, Synthesis, Structure and Unique Chemial Property of a First Fluorine-Containing Porphycene, Org. Lett., Vol.5, No.16, 2845-2848, 2003.09.
73. T. Hayashi, Y. Nakashima, K. Ito, T. Ikegami, I. Aritome, A. Suzuki, Y. Hisaeda, Synthesis, Structure and Unique Chemial Property of a First Fluorine-Containing Porphycene, Org. Lett., Vol.5, No.16, 2845-2848, 2003.09.
74. H. Shimakoshi, T. Inaoka, Y. Hisaeda, Solid-solid synthesis of a hydrophobic vitamin B12 having a benzo-18-crown-6 moiety at the C10 position of the corrin ring, Tetrahedron Lett., 10.1016/S0040-4039(03)01587-9, 44, 34, 6421-6424, Vol.44, No.34, 6421-6424, 2003.08.
75. H. Shimakoshi, T. Inaoka, Y. Hisaeda, Solid-solid synthesis of a hydrophobic vitamin B12 having a benzo-18-crown-6 moiety at the C10 position of the corrin ring, Tetrahedron Lett., 10.1016/S0040-4039(03)01587-9, 44, 34, 6421-6424, Vol.44, No.34, 6421-6424, 2003.08.
76. T. Hayashi, T. Matsuo, K. Harada, Y. Hisaeda, S. Hirota, N. Funasaki, Role of Heme-Propionate Side Chains in Myoglobin Function, J. Inorg. Biochem., 10.1016/S0162-0134(03)80489-0, 96, 1, 50-50, Vol.96, 50, 2003.07.
77. H. Shimakoshi, T. Kaieda, T. Matsuo, H. Sato, Y. Hisaeda, Syntheses of new water-soluble dicobalt complexes having two cobalt-carbon bonds and their ability for DNA cleavage, Tetrahedron Lett., 10.1016/S0040-4039(03)01252-8, 44, 28, 5197-5199, Vol.44, No.28, 5197-5199, 2003.07.
78. T. Hayashi, T. Matsuo, K. Harada, Y. Hisaeda, S. hirota, N. Funasaki, Role of Heme-Propionate Side Chains in Myoglobin Function, J. Inorg. Biochem., 10.1016/S0162-0134(03)80489-0, 96, 1, 50-50, Vol.96, 50, 2003.07.
79. H. Shimakoshi, T. Kaieda, T. Matsuo, H. Sato, Y. Hisaeda, Syntheses of new water-soluble dicobalt complexes having two cobalt-carbon bonds and their ability for DNA cleavage, Tetrahedron Lett., 10.1016/S0040-4039(03)01252-8, 44, 28, 5197-5199, 2003.07.
80. T. Hayashi, T. Matsuda, Y. Hisaeda, Enhancement of Peroxygenase Activity of Horse Heart Myoglobin by Modification of Heme-propionate Side Chains, Chem. Lett., 10.1246/cl.2003.496, 32, 6, 496-497, Vol.32, No.6, 496-497, 2003.06.
81. H. Shimakoshi, A. Nakazato, M. Tokunaga, K. Katagiri, K. Ariga, J. Kikuchi, Y. Hisaeda, Hydrophobic Vitamin B12. Part 18. Preparation of a sol-gel modified electrode immobilized with vitamin B12 derivative and its reductive dehalogenation activity, J. Chem. Soc., Dalton Trans., 10.1039/b212863b, 11, 2308-2312, 2308-2312, 2003.06.
82. H. Maeda, A. Osuka, Y. Ishikawa, I Aritome, Y. Hisaeda, H. Furuta, N-Confused Porphyrin-Bearing meso-Perfluorophenyl Groups: A Potential Agent That Forms Stable Square-Planar Complexes with Cu(II) and Ag(III), Org. Lett., 10.1021/ol34227l, 5, 8, 1293-1296, Vol.5, No.8, 1293-1296, 2003.05.
83. F. Tani, M. Matsu-ura, K. Ariyama, T. Setoyama, T. Shimada, S. Kobayashi, T. Hayashi, T. Matsuo, Y. Hisaeda, Y. Naruta, Iron Twin-Coronet Porphyrins as Models of Myoglobin and Hemoglobin: Amphibious Electrostatic Effects of Overhanging Hydroxyl Groups for Successful CO/O2 Discrimination, Chem. Eur. J., 10.1002/chem.200390096, 9, 4, 862-870, Vol.9, No.4, 862-870, 2003.02.
84. K. Sakurai, R. Iguchi, K. Koumoto, T. Kimura, M. Mizu, Y. Hisaeda, S. Shinkai, Polysaccharide-Polynucleotide Complexes VIII. Cation-Induced Complex Formation between
Polyuridylic Acid and Schizophyllan, Biopolymers, 10.1002/bip.10189, 65, 1, 1-9, Vol.65, 1-9, 2002.09.
85. T. Hayashi, H. Dejima, T. Matsuo, H. Sato, D. Murata, Y. Hisaeda, Blue Myoglobin Reconstituted with an Iron Porphycene Shows Extremely High Oxygen Affinity, J. Am. Chem. Soc., 10.1021/ja0265052, 124, 38, 11226-11227, Vol.124, No.38, 11226-11227, 2002.09.
86. I. Aritome, H. Shimakoshi, Y. Hisaeda, 3,6,13,19-Tetrabromo-2,7,12,17-tetrapropylporphycene, Acta Cryst., 10.1107/S0108270102013483, 58, O563-O564, Vol. C58, 563-564, 2002.08.
87. H. Shimakoshi, M. Koga, Y. Hisaeda, Synthesis, Characterization, and Redox Behavior of New Dicobalt Complexes Having Monoanionic Imine/Oxime-type Ligands, Bull. Chem. Soc. Jpn., 10.1246/bcsj.75.1553, 75, 7, 1553-1558, Vol.75, No.7, 1553-1558, 2002.07.
88. T. Hayashi, T. Aya, N. Nonoguchi, T. Mizutani, Y. Hisaeda, S. Kitagawa, H. Ogoshi, Chemical Recognition and Chiral Induction by Use of Zinc Porphyrin Dimers, Tetrahedron, Vol. 58, 2803-2811, 2002.04.
89. T. Hayashi, T. Matsuo, Y. Hitomi, K. Okawa, A. Suzuki, Y. Shiro, T. Iizuka, Y. Hisaeda, H. Ogoshi, Contribution of Heme-Propionate Side Chains to Structure and Function of Myoglobin:
Chemical Approach by Artificially Created Prosthetic Groups, J. Inorg. Biochem., 10.1016/S0162-0134(02)00423-3, 91, 1, 94-100, Vol.91, 94-100, 2002.01.
90. T. Hayashi, Y. Hisaeda, New Functionalization of Myoglobin by Chemical Modification of Heme-Propionates, Acc. Chem. Res., 10.1021/ar000087t, 35, 1, 35-43, Vol. 35, 35-43, 2002.01.
91. T. Hayashi, T. Ando, T. Matsuda, H. Sato, T. Matsuo, Y. Hisaeda, Chemical Properties of Reconstituted Myoglobins with Functionalized Hemin Derivatives, J. Inorg. Biochem., 86, 1, 57-57, Vol. 86, No. 1, 57, 2001.08.
92. K. Ariga, K. Tanaka, K. Katagiri, J. Kikuchi, H. Shimakoshi, E. Ohshima, Y. Hisaeda, Langmuir Monolayer of Organoalkoxysilane for vitamin B12-modified Electrode, Physical Chemistry Chemical Physics, 10.1039/b100974p, 3, 16, 3442-3446, Vol. 3, 3442-3446, 2001.08.
93. H. Dejima, T. Hayashi, T. Matsuo, Y. Hisaeda, New Myoglobin Reconstituted with an Iron Porphycene as a Structural Isomer of Heme Moiety, J. Inorg. Biochem., 86, 1, 200-200, Vol. 86, No. 1, 200, 2001.08.
94. T. Ando, T. Hayashi, H. Sato, Y. Hisaeda, Photoinduced Electron Transfer within an Artificially Created Protein-protein Complex, J. Inorg. Biochem., 86, 1, 124-124, Vol. 86, No. 1, 124, 2001.08.
95. H. Shimakoshi, W. Ninomiya, Y. Hisaeda, Reductive Coupling of benzyl Bromide Catalyzed by a Novel Dicobalt Complex Having Two Salen Units, J. Chem. Soc., Dalton Trans., 10.1039/b010022f, 13, 1971-1974, No. 13, 1971-1974, 2001.07.
96. Y. Hitomi, T. Hayashi, K. Wada, T. Mizutani, Y. Hisaeda, H. Ogoshi, Interprotein Electron Transfer Reaction Regulated by an Artificial Interface, Angew. Chem. Int. Ed., 10.1002/1521-3773(20010316)40:6<1098::AID-ANIE10980>3.0.CO;2-G, 40, 6, 1098-+, Vol. 40, No. 6, 1098-1101, 2001.03.
97. T. Hayashi, T. Ando, T. Matsuda, H. Yonemura, S. Yamada, Y. Hisaeda, Introduction of a Specific Binding Domain on Myoglobin Surface by New Chemical Modification, J. Inorg. Biochem., 10.1016/S0162-0134(00)00153-7, 82, 1-4, 133-139, Vol. 82, 133-139, 2000.12.
98. Y. Hisaeda, T. Nishioka, Y. Inoue, K. Asada, T. Hayashi, Electrochemical Reactions Mediated by Vitamin B12 Derivatives in Organic Solvents, Coordination Chemistry Review, 10.1016/S0010-8545(99)00222-2, 198, 21-37, Vol. 198, No. 1, 21-37, 2000.04.
99. T. Hayashi, K. Okazaki, H. Shimakoshi, F. Tani, Y. Naruta, Y. Hisaeda, Synthesis and Properties of Alkylperoxocobalt(III) Porphyrin and Porphycene, Chem. Lett., 2, 90-91, No.2, 90-91, 2000.02.
100. H. Shimakoshi, M. Tokunaga, K. Kuroiwa, N. Kimizuka, Y. Hisaeda, Preparation and electrochemical behaviour of hydrophobic vitamin B12 covalently immobilized onto platinum electrode, Chem. Commun., 10.1039/b309457j, 1, 50-51, 50-51, 2000.01.
101. T. Hayashi, Y. Hitomi, T. Ando, T. Mizutani, Y. Hisaeda, S. Kitagawa, H. Ogoshi, Peroxidase Activity of Myoglobin Is Enhanced by Chemical Mutation of Heme-Propionates, J. Am. Chem. Soc., 10.1021/ja9841005, 121, 34, 7747-7750, Vol. 121, No.34, 7747-7750, 1999.09.
102. T. Hayashi, Y. Hitomi, T. Takimura, A. Tomokuni, T. Mizutani, Y. Hisaeda, T.Ogoshi, New Approach to the Construction of Artificial Hemoprotein Complex, Coordination Chemistry Review, 192, 961-974, Vol. 190, pp.961-974, 1999.09.
103. T. Hayashi, Y. Hitomi, Y. Hisaeda, S. Kitagawa, Enhancement of Peroxidase Activity by Use of Reconstituted Myoglobin, J. Inorg. Biochem., 74, 1-4, 156-156, Vol. 74, No. 1-4, p.156, 1999.07.
104. T. Hayashi, A. Tomokuni, T. Mizutani, Y. Hisaeda, H. Ogoshi, Interfacial Recognition between Reconstituted Myoglobin Having Charged Binding Domain and Electron Acceptor via Electrostatic Interaction, Chemistry Letters, 10.1246/cl.1998.1229, 12, 1229-1230, No.12, pp.1229-1230, 1998.12.
105. A. Tanaka, S. Shimada, T. Hirohashi, T. Hayashi, Y. Hisaeda, Molecular Recognition by Novel Macrotetracyclic Cyclophanes Having Dipeptide Segments, Chemistry Letters, 10.1246/cl.1998.1109, 11, 1109-1110, No.11,pp.1109-1110, 1998.11.
106. Y. Hisaeda, A. Ogawa, T. Ohno, Y. Murakami, Hydrophobic Vitamin B12. Part 15. Carbon-skeleton Rearrangement Reactions Mediated by Hydrophobic Vitamin B12 Covalently Bound to an Anionic Lipid Species in Aqueous Media, Inorganica Chimica Acta,, 10.1016/S0020-1693(97)06036-2, 273, 1-2, 299-309, Vol.273, No.1-2, pp.299-309, 1998.05.
107. A. Tanaka, S. Fujiyoshi, K. Motomura, O. Hayashida, Y. Hisaeda, Y. Murakami, Preparation and Host-Guest Interactions of Novel Cage-type Cyclophanes Bearing Chiral Binding Sites Provided by Dipeptide Residues, Tetrahedron, 10.1016/S0040-4020(98)00218-X, 54, 20, 5187-5206, Vol.54, No.20, pp.5187-5206, 1998.05.
Presentations
1. Yoshio Hisaeda, Bioinspired Catalytic Reactions Using Vitamin B12 Derivative , 11th International Conference on Porphyrins & Phthalocyanines (ICPP-11) , 2021.06.
2. Yoshio Hisaeda, International Education Programs and Student Mobility Programs in Kyushu University, School of Engineering, and Graduate School of Engineering, 9th Asian Engineering Deans Summit (AEDS-2019), 2019.05.
3. Yoshio Hisaeda, Bioinspired Catalysts Lessons from Vitamin B12 Enzymes, 2019 National Taiwan Normal University (NTNU)-Kyushu University (Kyushu U) Joint Forum on Facilitating Interdisciplinary Research and Education, 2019.05.
4. Yoshio Hisaeda, Electrochemical Perfluoroalkylations of Arenes and Heteroarenes by Bioinspired Catalytic System, 13th International Symposium on Organic Reaction (ISOR-13) , 2018.11.
5. Yoshio Hisaeda, Electrochemical Perfluoroalkylation of Arenes and Heteroarenes Catalyzed by Vitamin B12 Derivative, International Conference on Coordination Chemistry (ICCC), 2018.08.
6. Yoshio Hisaeda, Facile Synthesis of Porphycene Derivatives and Reactivity of Cobalt Porphycene, 10th International Conference on Porphyrins & Phthalocyanines (ICPP-10), 2018.07.
7. Yoshio Hisaeda, Bioinspired Catalytic System with Vitamin B12 Function, Conference on New Advances in the Chemistry of Porphyrinoids, 2018.12.
8. Yoshio Hisaeda, Bioinspired Catalyst with Vitamin B12 Functions Using Photochemical and Electrochemical Methods, 5th CMS International Symposium (CMS-5) on Photofunctional Chemistry and Molecular Systems, 2017.12.
9. Yoshio Hisaeda, Bioinspired Catalytic Reactions Using Vitamin B12 Derivative, 6th Asian Conference on Coordination Chemistry(ACCC6), 2017.07.
10. Yoshio Hisaeda, Bioinspired Catalyst with Vitamin B12 Functions Activated by Photochemical or Electrochemical Methods, 26th International Conference on Coordination and Bioinorganic Chemistry, 2017.06.
11. Yoshio Hisaeda, Bioinspired Catalysts with Vitamin B12 Function Activated by Photochemical and Electrochemical Methods, 2nd International Symposium on Precisely Designed Catalysts with Customized Scaffolding, 2017.05.
12. Yoshio Hisaeda, Bioinspired Catalytic Reaction Lessons from Vitamin B12 Enzyme, 8th Asian Biological Inorganic Chemistry Conference (AsBIC8-2016), 2016.12.
13. Yoshio Hisaeda, Bioinspired Catalysts with Vitamin B12 Derivatives Using Photochemical and Electrochemical Methods, International Symposium on Catalysis and Fine Chemicals in Taipei-2016 (C&FC-2016), 2016.11.
14. Yoshio Hisaeda, Bioinspired Catalysts based on Vitamin B12 Chemistry, 9th International Conference on Porphyrins & Phthalocyanines(ICPP-9), 2016.07.
15. Yoshio Hisaeda, Bioinspired Catalysts with Vitamin B12 Functions Using Photosensitizer or Electrochemical Method, The 12th International Symposium on Organic Reactions and The 6th German-Japanese Symposium on Electrosynthesis (ISOR-12 and GJSE-6), 2016.04.
Membership in Academic Society
  • Society of Biological Inorganic Chemistry
  • International Society of Electrochemistry
  • Electrochemical Society
  • Society of Porphyrins and Phthalocyanines
  • International Society of Heterocyclic Chemistry
  • American Chemical Society
Awards
  • Redox Behavior and Electrochemical Catalytic Function of B12-Hyperbranched Polymer
    Bull. Chem. Soc. Jpn., 2010, 83, 1439-1446.
  • Isolable Iron(II)-Porphycene Derivative Stabilized by Introduction of Trifluoromethyl Groups on the Ligand Framework
    Bull. Chem. Soc. Jpn., 2008, 81, 76-83.
Educational
Educational Activities
Coordination Chemistry
Course Outline: After an introduction of coordination compounds, their structures and reactivity will be introduced. This course covers the fundamental principles, theories, and applications concerning coordination compounds.
Course Plan:
1. Introduction: Coordination compounds in our life
2. Nomenclature of coordination compounds
3. The coordination bond: Crystal field theory
4. Stereochemistry of coordination compounds
5. Preparations and reactions of coordination compounds
6. Complex ion stability constants
7. Kinetics and mechanisms of reactions of coordination compounds
8. Organometallic chemistry and current research topics