Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Kenta Goto Last modified date:2019.06.28

Assistant Professor / Department of Chemistry, Graduate School of Sciences / Department of Applied Molecular Chemistry / Institute for Materials Chemistry and Engineering

1. Keita Tani, Toru Yashima, Kanae Miyanaga, Kazushige Hori, Kenta Goto, Fumito Tani, Yume Habuka, Katsuaki Suzuki, Katsuyuki Shizu, Hironori Kaji, Carbazole and benzophenone based twisted donoracceptor systems as solution processable green thermally activated delayed fluorescence organic light emitters, Chemistry Letters, 10.1246/cl.180438, 47, 9, 1236-1239, 2018.01, New donor-acceptor (D-A) and donor-acceptor-donor (D-AD) systems with carbazole and benzophenone moieties as donor and acceptor, respectively, have been synthesized. Photolumi-nescence quantum yields of D-A and D-A-D molecules in thin film were 76 and 73%, respectively. Solution-processed organic light-emitting diodes containing these D-A and D-A-D molecules as emitters showed the maximum external quantum efficiencies of 6.9 and 10.4% with a peak wavelength of 520 and 521 nm, respectively..
2. Shuhei Ogata, Naoto Goto, Shoya Sakurai, Ayumi Ishii, Miho Hatanaka, Koushi Yoshihara, Ryota Tanabe, Kyosuke Kayano, Ryo Magaribuchi, Kenta Goto, Miki Hasegawa, Alkyl chain elongation and acyl group effects in a series of Eu/Tb complexes with hexadentate π-electronic skeletons and their enhanced luminescence in solutions, Dalton Transactions, 10.1039/c7dt04899h, 47, 21, 7135-7143, 2018.01, Five Eu complexes with long alkyl chain groups, abbreviated as EuLCx ("x" indicates the number of methylene groups: x = 8, 12, 14, 18, and 22), were synthesized to evaluate their structural and luminescence properties in chloroform. The mother helicate Eu complex, EuL, which has two bipyridine moieties bridged by an ethylenediamine, has been previously reported. A reduced form in which the azomethine groups of L also coordinated to the Eu ion, EuLH, was newly prepared. EuLH also adopts a helicate molecular structure based on single crystal X-ray structural analysis. The amine hydrogens of the bridging ethylenediamine of LH are active sites for substitution and were exchanged with five different alkyl chains to form EuLCx. Luminescence band positions and shapes of EuLCx in chloroform were completely identical, with a quantum yield of 37.1 ± 1.2 and a lifetime of around 1.25 ms. This indicates that the environments surrounding the Eu ion in the various complexes are all similar. Luminescence quantum yields of TbLH and TbLC18 are also strengthened, 48.7% in acetonitrile and 55% in chloroform, respectively. Potential energy surfaces were also described by using density functional theory, suggesting the possibility of a 1:2 complex of Eu and the ligand as a main luminescent species in solutions. This 1:2 complexation forms Eu-oxygen coordination using acyl groups. It indicates that the acyl group modification results in a different structure from the mother complexes..
3. Shuhei Ogata, Hiroaki Komiya, Naoto Goto, Ryota Tanabe, Kunihisa Sugimoto, Shogo Kawaguchi, Kenta Goto, Miho Hatanaka, Ayumi Ishii, Miki Hasegawa, Strong luminescent europium complexes induced by the unprecedented anti-chelate effect of acyl groups on a N6-hexadentate ligand, Chemistry Letters, 10.1246/cl.190140, 48, 6, 593-596, 2019.01, An acyl group derived-bipyridine ligand and Eu form 3:2 complexes. The structure and luminescence behaviour were evaluated, and we found an unexpected bi-nuclear complex system, which induces efficiently the luminescence of europium ion. This observation is discussed from experimental and theoretical viewpoints..
4. Md Awlad Hossain, Ken Ichi Yamashita, Kazunori Hirabayashi, Toshio Shimizu, Kenta Goto, Ken Ichi Sugiura, Thiophene-Fused Dinaphthopentaphenes
Versatile Applications of 1,2-Bis(pyren-2-yl)aromatics in the Synthesis of π-Expanded Molecules, ChemistrySelect, 10.1002/slct.201700152, 2, 16, 4343-4348, 2017.01, Thiophene-fused dinaphtho[8,1,2-opq:2′,1′,8′-uva]pentaphenes (DNPPs) were synthesized and characterized by using our previously reported strategy. The Suzuki-Miyaura coupling of the boronic acid ester of pyrene with dibromothiophenes, 2,3-dibromo- and 3,4-dibromothiophenes, afforded the corresponding bis(pyren-2-yl)thiophenes. The subsequent oxidation reaction afforded the desired π-expanded molecules. Reflecting the DNPP moieties, the obtained molecules show properties characteristic of π-expanded molecules, such as amphoteric multiredox behaviors and light absorption in the visible region. The oxidized product of 3,4-bis(pyren-2-yl)thiophene, which contains an ortho-quinoidal structure, i. e., benzo[c]thiophene, was isolated and spectroscopically characterized. Because these molecules possess the [5]helicene structure, optical resolution of enantiomers has been carried out using high-performance liquid chromatography..
5. Shohei Tomita, Kazunori Hirabayashi, Toshio Shimizu, Kenta Goto, Ken ichi Sugiura, Basic Photophysical Properties of meso-Bis(pyren-2-yl)porphyrin
An Isomer of Pyrene-Substituted Porphyrins, Synthesis, 10.1055/s-0036-1588715, 49, 10, 2182-2186, 2017.05, The Suzuki-Miyaura coupling reaction of pyren-2-yl boronic acid ester with a meso-dibromodiphenylporphyrin derivative was carried out to give another pyrene-substituted porphyrin. The electrophilic substitution reaction occurred selectively on the porphyrin nucleus of this molecule. The introduced pyrenes acted as a light-harvesting antenna..
6. Minoru Yamaji, Shin Ichiro Kato, Kazuhiro Tomonari, Michitaka Mamiya, Kenta Goto, Hideki Okamoto, Yosuke Nakamura, Fumito Tani, Blue Fluorescence from BF2 Complexes of N,O-Benzamide Ligands
Synthesis, Structure, and Photophysical Properties, Inorganic Chemistry, 10.1021/acs.inorgchem.7b02013, 56, 20, 12514-12519, 2017.10, Small molecules having intense luminescence properties are required to promote biological and organic material applications. We prepared five types of benzamides having pyridine, pyridazine, pyrazine, and pyrimidine rings and successfully converted them into three types of the difluoroboronated complexes, Py@BAs, as novel blue fluorophores. Py@BA having a pyridine moiety (2-Py@BA) showed no fluorescence in solution, whereas Py@BAs of pyridazine and pyrazine moieties (2,3-Py@BA and 2,5-Py@BA, respectively) emitted blue fluorescence with quantum yields of ca. 0.1. Transient absorption measurements using laser flash photolysis of the Py@BAs revealed the triplet formation of 2,3- and 2,5-Py@BAs, while little transient signal was observed for 2-Py@BA. Therefore, the deactivation processes from the lowest excited singlet state of fluorescent 2,3- and 2,5-Py@BAs consist of fluorescence and intersystem crossing to the triplet state while that of the nonfluorescent Py@BA is governed almost entirely by internal conversion to the ground state. Conversely, in the solid state, 2-Py@BA emitted intense fluorescence with a fluorescence quantum yield as high as 0.66, whereas 2,3- and 2,5-Py@BAs showed fluorescence with quantum yields of ca. 0.2. The crystal structure of 2-Py@BA took a herringbone packing motif, whereas those for 2,3- and 2,5-Py@BAs were two-dimensional sheetlike. On the basis of the difference in crystal structures, the emission mechanism in the solid state was discussed..
7. Ryotaro Fujii, Md Awlad Hossain, Hisato Akimoto, Kazunori Hirabayashi, Toshio Shimizu, Kazuhiko Akiyama, Kenta Goto, Hiroyuki Nishikawa, Ken Ichi Yamashita, Ken Ichi Sugiura, Synthesis of Tetra(3-thienyl)biphenoquinone and its Charge Transfer Complex with Perylene, Asian Journal of Organic Chemistry, 10.1002/ajoc.201700560, 7, 1, 171-178, 2018.01, Tetra(thienyl)biphenoquinones were designed and synthesized. An oxidative coupling of 2,6-bis(3-thienyl)phenol with PbO2 in acetic acid afforded the corresponding biphenoquinone along with 2,6-bis(3-thienyl)-p-benzoquinone. This biphenoquinone showed properties characteristic of a π-expanded quinone, that is, positively shifted reduction potential and light absorption in the visible region. In contrast to kinetically protected biphenoquinones with bulky substituents at the ortho-positions of carbonyls, the title compounds take a planar structure because of the small steric repulsion of the five-membered thiophene rings. Its charge transfer complex with perylene is characterized by a well-overlapped mixed stack..
8. Minoru Yamaji, Hideki Okamoto, Kenta Goto, Shin ichiro Kato, Fumito Tani, Yosuke Nakamura, Synthesis of isomeric coumarin-fluorene hybrids by photocyclization and the photophysical features, Tetrahedron Letters, 10.1016/j.tetlet.2018.02.033, 59, 13, 1216-1219, 2018.03, We prepared isomeric compounds 2a and 2b having fused skeletons of coumarin and fluorene by photochemical cyclization of olefin 1. They were successfully separated by chromatography, and characterized by NMR spectroscopic and X-ray crystallographic analyses. The molecular structure of 2a was nonplanar due to the repulsion between the carbonyl group of the coumarin moiety and the methylene group at 9-position on the fluorene skeleton whilst that of 2b was planar. They showed different absorption and fluorescence features in solution whereas their spectral profiles of triplet–triplet absorption and phosphorescence were similar to each other..
9. Tani, Keita, Kato, Haruka, Sakata, Naoya, Yashima, Toru, Kubono, Koji, Hori, Kazushige, Tao, Keisuke, K. Goto, 谷 文都, Takemura, Hiroyuki, Sakakibara, Keita, Tsujii, Yoshinobu, Synthesis and Radical Polymerization of Acrylamides Having One or Two 3-Carbazolylmethyl Moieties and Properties of the Formed Polymers, CHEMISTRY LETTERS, 10.1246/cl.160899, 46, 1, 85-87, 2017.01.
10. M. Shibahara, M. Watanabe, T. Miyazaki, K. Goto, T. Shinmyozu, Synthesis of Dibromo[3.3]paracyclophanes, Synthesis-Stuttgart, 2016, 48, 1197-1201., 2016.01.
11. V. L. Mishra, T. Furuyama, N. Kobayashi, K. Goto, T. Miyazaki, J.-S. Yang, T. Shinmyozu, Synthesis, Optical Properties, and Electronic Structures of Tetrakis(pentafluoro-phenyl)tetrathiaisophlorin Dioxide, Chem. Eur. J. , 2016, 22, 9190-9197., 2016.01.
12. M. Watanabe, N. Uemura, S. Ida, H. Hagiwara, K. Goto, T. Ishihara, 5,5'-alkylsubsituted indigo for solution-processed optoelectronic devices, Tetrahedron, 2016, 72, 4280-4287., 2016.01.
13. Md. A. Hossain, K. Akiyama, K. Goto, K.-i. Sugiura, Thermal reductive disproportionation of 3,3',5,5'-tetraphenyldiphenoquinone with drastic color change: Potential prototype of data storage advanced materials, ChemistySelect, 2016, 1, 3784-3790, 2016.01.
14. Md. E. Halim, A. Bandyopadhyay, L.-S. Sun, K. Tao, Y. S. Sangvikar, T. Miyazaki, M. Watanabe, K. Ideta, T. Matsumoto, K. Goto, Teruo Shinmyozu, Synthesis of bromo- and iodo-substituted pyromellitic diimide-based [2+2]- and [3+3]macrocycles, and their absorption spectra and electrochemical and inclusion properties, Tetrahedron Letters, 2015, 56, 6970-6974., 2015.10.
15. T. Miyazaki, M. Shibahara, J. Fujishige, M. Watanabe, K. Goto, T. Shinmyozu, Synthesis and Electronic and Photophysical Properties of [2.2]- and [3.3]Paracyclophane-Based Donor-Donor'-Acceptor Triads, Journal of Organic Chemistry, 2014, 79, 11440-11453.
16. M. Shibahara, M. Watanabe, K. Goto, T. Miyazaki, T. Shinmyozu, Structural properties of five- and six-layered [3.3]metacyclophanes, Tetrahedron Letters, 2014, 55, 7089-7093.
17. M. Shibahara, M. Watanabe, T. Matsumoto, K. Goto, T. Shinmyozu, Crystal structure of a four-layered [3.3](3,5)pyridino-phane, Acta Crystallographica Section E, 2014, 70, 447-450, 2014.11.
18. M. Shibahara, M. Watanabe, K. Goto, T. Shinmyozu, Four-layered [3.3]metacyclophane with ethenetetracarbonitrile, Acta Crystallographica Section E, 2014, 70, o625-o626., 2014.01.
19. Y. Matsunaga, K. Goto, K. Kubono, K. Sako, and T. Shinmyozu , Photoinduced Color Change and Photomechanical Effect of Naphthalene Diimides Bearing Alkylamine Moieties in the Solid State, Chemistry - A European Journal, 2014, 20, 7309-7316., 2014.01.
20. Kuo, Chi-Hsien; Huang, Ding-Chi; Peng, Wei-Tao; Goto, Kenta; Chao, Ito; Tao, Yu-Tai, Substituent effect on the crystal packing and electronic coupling of tetrabenzocoronenes: a structure-property correlation, JOURNAL OF MATERIALS CHEMISTRY C, 10.1039/c4tc00296b, 2, 20, 3928-3935, 2014, 2, 3928-3925., 2014.01.
21. Ohyama, Kazuko; Goto, Kenta; Shinmyozu, Teruo; Yamamoto, Norifumi; Iizumi, Shota; Miyagawa, Masaya; Nakata, Munetaka; Sekiya, Hiroshi, Infrared spectroscopic studies on 4-amino-6-oxopyrimidine in a low-temperature Xe matrix and crystalline polymorphs composed of double hydrogen-bonded ribbons, Chemical Physics Letters, 10.1016/j.cplett.2014.01.059, 595, 138-143, 2014, 595-596, 138-143., 2014.03.
22. Motonori Watanabe, Ching-Ting Chien, Yan-Duo Lin, Yuan Jay Chang, Yuh-Sheng Wen, Kenta Goto, Masahiko Shibahara, Teruo Shinmyozu, Tahsin J. Chow, Synthesis, physical properties, and structure of TIPS-difuranoacenes, Tetrahedron Letters,, 2014, 55, 1424–1427, 2015.02.
23. Takahisa Uchise, Kenta Goto,* Aya Harano and Teruo Shinmyozu*, Selective alcohol adsorption in a uniformly ordered array of lipophilic mesopores by a giant macrocycle, RSC Advances, DOI: 10.1039/c3ra45716h, 4, 6014-6018, 2014.01.
24. K. Kubono, K. Tani, K. Yokoi, T. Shinmyozu and K. Goto, Di-µ2-acetato-1:2κ2O:O';2:3κ2O:O'-bis{µ2-4,4'-dichloro-2,2'-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]diphenolato}-1:2κ6O,N,N',O':O,O';2:3κ6O,O':O,N,N',O'-tricadmium(II), Acta Crystallographica Section E, E69, m629-m630., 2013.10.
25. Motonori Watanabe, Yuan Jay Chang, Shun-Wei Liu, Ting-Han Chao, Kenta Goto, Md. Minarul Islam, Chih-Hsien Yuan, Yu-Tai Tao, Teruo Shinmyozu and Tahsin J. Chow, The synthesis, crystal structure and charge-transport properties of hexacene, Nature Chemistry, doi:10.1038/nchem.1381, Vol. 4, 574-578., 2012.06, [URL].
26. Koji Kubono, Teruo Shinmyozu, Kenta Goto, Tsuyoshi Tsujioka and Keita Tani, 1,2-Bis[5-(9-ethyl-9H-carbazol-3-yl)-2- methylthiophen-3-yl]-3,3,4,4,5,5-hexa- fluorocyclopentene, Acta Crystallographica Section E, E67, o2194., 2011.08.
27. Masahiko Shibahara, Motonori Watanabe, Chang Yuan, Kenta Goto, and Teruo Shinmyozu, Structural properties of charge-transfer complexes of multilayered [3.3]paracyclophanes, Tetrahedron Letters,, 52 (26) 3371-3375., 2011.04.
28. Aya Harano, Minako Tanaka, Takeshi Nakagaki, Masahiko Annaka, Keiko Ideta, Kenta Goto, Teruo Shinmyozu, Changing the volume of a giant macrocycle: the swelling of the macrocycle with organic solvents, Organic & Biomolecular Chemistry, DOI: 10.1039/c1ob05272a, 9 (10), 3611-3614, 2011.03.
29. T. Nakagaki, A. Harano, Y. Fuchigami, E. Tanaka, S. Kidoaki, Dr. T. Okuda, T. Iwanaga, K. Goto, T. Shinmyozu, Formation of Nanoporous Fibers by the Self-Assembly of a Pyromellitic Diimide-Based Macrocycle, Angewandte Chemie Internal Edition, 10.1002/anie.201004992, 49, (50), 9676-9679, 2010.12.
30. Motonori Watanabe, Kenta Goto, Mamoru Fujitsuka, Sachiko Tojo, Tetsuro Majima, and Teruo Shinmyozu, 2,1,3-Benzothiadiazole Dimers: Preparation, Structure, and Transannular Electronic Interactions of syn- and anti-[2.2](4,7)Benzothiadiazolophanes, Bulletin of the Chemical Society of Japan, doi:10.1246/bcsj.20100085, 83 (10), 1155-1161, 2010.10.
31. Motonori Watanabe, Kenta Goto, Masahiko Shibahara, and Teruo Shinmyozu, Synthesis, Structure, and Electronic and Photophysical Properties of Two- and Three-Layered [3.3]Paracyclophane-Based Donor-Acceptor Systems, The Journal of Organic Chemistry, DOI: 10.1021/jo100688m, 75 (18) 6104-6114, 2010.10.
32. Y. Miyahara, K. Goto, and T. Inazu., ChemInform Abstract: Synthesis and Properties of a Novel Tetraazamacrocycle Containing Two Bispidine Units, ChemInform, 10.1002/chin.200044171, 31, 44, 2010.10.
33. N. Dixit, K. Goto, L. Mishra, H.W. Roesky, Supramolecular architectures constructed with the skeletons of zinc(II) 2,2'-bipyridine and barbiturate anion: Synthesis and characterization, Polyhedron, 20 (4), 1299-1304, 2010.03.
34. Kenta Goto, Yuji Miyahara, and Teruo Shinmyozu, A Spherical Molecular Assembly Formed by the Interplay of Hydrophobic and Hydrogen Bonding Interactions. Formation of a Hexameric Ball, Tetrahedron Letters,, 51, 5, 832-835, 2010.01, [URL].
35. Shin-ichiro Kato, Yasuhiro Nonaka, Toshiaki Shimasaki, Kenta Goto, Teruo Shinmyozu., Novel pyromellitic diimide-based macrocycle with a linear pi-electronic system and bis(phenylethynyl)pyromellitic diimide: Syntheses, structures, photophysical properties, and redox characteristics, The Journal of Organic Chemistry, 73, 4063-4075., 2008.06.
36. Kenta Goto, Rieko Omae, Minoru Yamaji, Teruo Shinmyozu, J-type aggregation of a simple merocyanine skeleton: Spectral features and structure of 4-amino-6-oxopyrimidine, Journal of Photochemistry and Photobiology A: Chemistry, 194, 92-96., 2008.01, [URL].
37. E.-I. Rõõm, A. Kütt, I. Kaljurand, I. Koppel, I. Leito, I.-A. Koppel, M. Mishima, K. Goto, and Y. Miyahara, Brønsted Basicities of Diamines in the Gas Phase, Acetonitrile, and Tetrahydrofuran, Chemistry - A European Journal, 13(27), 7631-7643., 2007.09.
38. Kenta Goto and Teruo Shinmyozu, Regulated Formation of 2D Water Layers with Alternating Six-membered Quasi-planar and Chair Cluster Units by 1D Supramolecular Chain, Chemistry Letters, 36, 1100-1101., 2007.09.
39. Toshiaki Shimasaki, Shin-ichiro Kato, Keiko Ideta, Kenta Goto, and Teruo Shinmyozu, Synthesis and structural and photoswitchable properties of novel chiral host molecules: Axis chiral 2,2'-dihydroxy-1,1'-binapththyl-appended stiff-stilbene, The Journal of Organic Chemistry, 72 (4), 1073-1087., 2007.04.
40. Shin-ichiro Kato, Taisuke Matsumoto, Keiko Ideta, Toshiaki Shimasaki, Kenta Goto, and Teruo Shinmyozu, Supramolecular assemblies and redox modulation of pyromellitic diimide-based cyclophane via noncovalent interactions with naphthol, The Journal of Organic Chemistry, 71(13), 4723-4733., 2006.04.
41. Y. Miyahara, K. Goto, M. Oka, and T. Inazu., Remarkably Facile Ring-Size Control in Macrocyclization: Synthesis of Hemicucurbit[6]uril and Hemicucurbit[12]uril, Angewandte Chemie International Edition, 10.1002/anie.200460764, 43, 38, 5019-5022, 43(38), 5019-5022, 2004.01.
42. Y. Miyahara, K. Goto, and T. Inazu., A novel hindered macrocyclic tetramine containing two bispidine units. A new type of proton sponge, Tetrahedron Letters, 10.1016/S0040-4039(01)00341-0, 42, 17, 3097-3099, 42, 3097-3099, 2001.01.
43. V. Galasso, K. Goto, Y. Miyahara, B. Kovac, and L. Klasinc., On the structure and spectroscopic properties of bispidine, N,N-dimethyl-bispidine and a bis-bispidine macrocycle, Chemical Physics, 10.1016/S0301-0104(02)00331-2, 277, 3, 229-240, 277, 229-240, 2002.01.
44. M. Umemiya, K. Goto, S. Takaishi, H. Miyasaka, K.-i. Sugiura, M. Yamashita, H. Nishikawa, K. Kikuchi, I. Ikemoto, Y. Yokochi, H. Ito and S. Kuroda, New organic conductor (DMET)2CuCl2: Synthesis, structure and physical properties, J. Phys. IV France, 114, 589-590., 2004.01.
45. Yuji Miyahara, Kenta Goto, and Takahiko Inazu., Convenient Synthesis of 3,7-Diazabicyclo[3.3.1]nonane (Bispidine), Synthesis, 3, 364-366, 364-366, 2001.01.
46. T. Nishida, K. Goto, S. Kubuki, and T. Tamaki., 57Fe Mossbauer, XRD and DTA study of the crystallization behavior of calcium aluminate glass containing iron(III), Journal of Radioanalytical and Nuclear Chemistry, 246, 51-56, 2000.01.
47. Y. Miyahara, K. Goto, and T. Inazu., Synthesis and Properties of a Novel Tetraazamacrocycle Containing Two Bispidine Units, Chemistry Letters, 10.1246/cl.2000.620, 6, 620-621, 620-621, 2000.01.