研究者詳細 - 忍久保　洋

論文 - 忍久保　洋

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Synthesis of Oxygen-Substituted Hexa-peri-hexabenzocoronenes through Ir-Catalyzed Direct Borylation 査読有り国際誌

Yamaguchi Ryuichi, Hiroto Satoru, Shinokubo Hiroshi

ORGANIC LETTERS 14 巻 ( 10 ) 頁： 2472 - 2475 2012年5月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

Direct C-H borylation of hexa-peri-hexabenzocoronenes (HBCs) has been achieved under iridium catalysis, which allows efficient synthesis of hydroxy-substituted HBCs by oxidation of the boryl groups. Further oxidation of dihydroxy HBC with phenyliodine bis(trifluoroacetate) (PIFA) afforded tetraoxo-substituted HBC without any regioisomers, which can be considered as a π-extended quinone. © 2012 American Chemical Society.

DOI： 10.1021/ol300743f

Synthesis of Nickel(II) Azacorroles by Pd-Catalyzed Amination of a,a'-Dichlorodipyrrin NiII Complex and Their Properties 査読有り国際誌

Horie Miki, Hayashi Yosuke, Yamaguchi Shigeru, Shinokubo Hiroshi

CHEMISTRY-A EUROPEAN JOURNAL 18 巻 ( 19 ) 頁： 5919 - 5923 2012年5月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemistry - A European Journal

Synthesis of nickel(II) complexes of meso-aryl-substituted azacorroles was performed by Buchwald-Hartwig amination of a dipyrrin Ni II complex with benzylamine through C-N and C-C coupling. The highly planar structure of Ni II azacorroles was elucidated by X-ray diffraction analysis. 1H NMR analysis and nucleus independent chemical shift (NICS) calculation on Ni II azacorrole revealed its distinct aromaticity with [17]triaza-annulene 18π conjugation. In addition, acylation of azacorrole selectively afforded N- and C-acylated azacorroles depending on the reaction conditions, showing the dual reactivity of azacorroles. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/chem.201200485

Energy and Electron Transfer from Fluorescent Mesostructured Organosilica Framework to Guest Dyes 査読有り国際誌

Mizoshita Norihiro, Yamanaka Ken-ichi, Hiroto Satoru, Shinokubo Hiroshi, Tani Takao, Inagaki Shinji

LANGMUIR 28 巻 ( 8 ) 頁： 3987 - 3994 2012年2月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

Energy and electron transfer from frameworks of nanoporous or mesostructured materials to guest species in the nanochannels have been attracting much attention because of their increasing availability for the design and construction of solid photofunctional systems, such as luminescent materials, photovoltaic devices, and photocatalysts. In the present study, energy and electron-transfer behavior of dye-doped periodic mesostructured organosilica films with different host-guest arrangements were systematically examined. Fluorescent tetraphenylpyrene (TPPy)-silica mesostructured films were used as a host donor. The location of guest perylene bisimide (PBI) dye molecules, acting as an acceptor, could be controlled on the basis of the molecular design of the PBI substituent groups. PBI dyes with bulky substituents and polar anchoring groups were located at the pore surface with low self-aggregation, which induced efficient energy or electron transfer because of the close host-guest arrangement. However, PBI dye with bulky and hydrophobic substituents was located in the center of template surfactant micelles; the fluorescence emission from the host TPPy groups was hardly quenched when the host-guest distance was longer than the critical Förster radius (ca. 4.5 nm). The relationship between the energy or electron-transfer efficiency and the location of guest species in the channels of mesostructured organosilica was first revealed by molecular design of the PBI substituents. © 2012 American Chemical Society.

DOI： 10.1021/la204645k

Facile Synthesis of Biphenyl-Fused BODIPY and Its Property 査読有り国際誌

Hayashi Yosuke, Obata Naoki, Tamaru Masatomo, Yamaguchi Shigeru, Matsuo Yutaka, Saeki Akinori, Seki Shu, Kureishi Yuka, Saito Shohei, Yamaguchi Shigehiro, Shinokubo Hiroshi

ORGANIC LETTERS 14 巻 ( 3 ) 頁： 866 - 869 2012年2月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Organic Letters

A biphenyl-fused BODIPY was synthesized through a facile oxidative cyclization of peripheral aryl-substituents at the β-position of the BODIPY unit. The extended π-system of the fused BODIPY induces near-infrared (NIR) absorption and strong π - π interactions in the solid state. These features are beneficial for the application of the dye as a functional material. The biphenyl-fused BODIPY dye was demonstrated to exhibit photocurrent conversion ability on the basis of its n-type semiconducting property. © 2012 American Chemical Society.

DOI： 10.1021/ol2033916

Ensemble and Single-Molecule Spectroscopic Study on Excitation Energy Transfer Processes in 1,3-Phenylene-Linked Perylenebisimide Oligomers 査読有り国際誌

Bahng Hee Won, Yoon Min-Chul, Lee Ji-Eun, Murase Yuichi, Yoneda Tomoki, Shinokubo Hiroshi, Osuka Atsuhiro, Kim Dongho

JOURNAL OF PHYSICAL CHEMISTRY B 116 巻 ( 4 ) 頁： 1244 - 1255 2012年2月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

1,3-Phenylene-bridged perylenebisimide dimer (PBI2) and trimer (PBI3) were prepared along with monomer reference (PBI1) using perylene imide-anhydride 5 as a key precursor. 3,3-Dimethylbut-1-yl substituents were introduced at the 2,5-positions of perylenebisimide (PBI) to improve the solubilities of PBI oligomers. Actually, no serious aggregation of PBI2 and PBI3 was detected in their dilute CH2Cl2 solutions. Under these conditions, intramolecular electronic interactions among PBI chromophores have been revealed by measuring the photophysical properties at their ensemble and single-molecule levels. The excitation energy transfer times of PBI2 (0.16 ps) and PBI3 (0.60 ps) were determined from the two different observables, anisotropy depolarization, and singlet-singlet annihilation, respectively, which are considered as the incoherent Förster-type energy hopping (EEH) times as compared with the EEH time constant (1.97 ps) calculated on the basis of the Förster mechanism. The relatively short EEH times compared to similar PBI oligomers can be attributed to 1,3-phenylene linker, which assures a short distance between the chromophores and, as a consequence, makes it hard to treat the PBI unit as a point dipole. The limitation of point-dipole approximation to describe the PBI oligomers and additional through-bond type interactions can be attributed as the causes of the discrepancies in excitation energy transfer times. Considering these photophysical properties, we can suggest that 1,3-phenylene-linked PBI oligomers have potentials as molecular photonic devices including the artificial light-harvesting system. © 2011 American Chemical Society.

DOI： 10.1021/jp208855u

Synthesis and oxidation of cyclic tetraindole 査読有り国際誌

Nakamura Shoichi, Hiroto Satoru, Shinokubo Hiroshi

CHEMICAL SCIENCE 3 巻 ( 2 ) 頁： 524 - 527 2012年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemical Science

A cyclic indole tetramer has been synthesized via an iridium-catalysed C-H borylation-cross coupling sequence. The tetraindole has a highly distorted structure, but can be oxidized with bromine and water into a highly planar macrocycle. The oxidized macrocycle can capture metal ions in its inner cavity as a novel porphyrin analogue, accompanied by a significant colour change from purple to blue or black. © 2012 The Royal Society of Chemistry.

DOI： 10.1039/c1sc00665g

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Mesoporous Organosilica Hybrids Consisting of Silica-Wrapped p-p Stacking Columns 査読有り国際誌

Mizoshita Norihiro, Tani Takao, Shinokubo Hiroshi, Inagaki Shinji

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 51 巻 ( 5 ) 頁： 1156 - 1160 2012年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Angewandte Chemie - International Edition

A new class of periodic mesoporous organosilica (PMO) materials with a columnar π-stacking arrangement of the framework organic groups has been prepared from disklike precursors with hydrophobic perylene bisimide (PBI) cores (see picture). The PBI-bridged PMOs exhibit exciton coupling and efficient formation of mobile radical spins by electron doping within the pore walls. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/anie.201105394

A meso-Spiro[Cyclopentadiene-Isoporphyrin] from a Phenylethynyl Porphyrin Platinum(II) Pincer Complex 査読有り国際誌

Anabuki Shoma, Shinokubo Hiroshi, Aratani Naoki, Osuka Atsuhiro

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 51 巻 ( 13 ) 頁： 3174 - 3177 2012年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Angewandte Chemie - International Edition

A good catch: The oxidation of a phenylethynyl Pt II pincer complex with iodine led to formal reductive elimination but without the liberation of Pt II, which was caught by the 2-pyridyl substituents on the Ni II porphyrin. The unique reactivity of the Pt II pincer complex led to the formation of a meso-spiro[cyclopentadiene- isoporphyrin]. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/anie.201109091

Oxidative Annulation of ss-Aminoporphyrins into Pyrazine-Fused Diporphyrins 査読有り国際誌

Akita Masanari, Hiroto Satoru, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 51 巻 ( 12 ) 頁： 2894 - 2897 2012年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Angewandte Chemie - International Edition

Dimers are a girl's best friend: The oxidative fusion reaction of β-aminoporphyrins with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under high-dilution conditions furnishes pyrazine-fused diporphyrins 1 in high yields. In a further application of the reaction, the oxidation of a 5,10,15,20-tetraphenylporphyrin derivative provides a singly linked diaminodiporphyrin 2 along with the pyrazine-fused diporphyrin (see scheme; only core structures are shown). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/anie.201108037

Gram-Scale Synthesis of Nickel(II) Norcorrole: The Smallest Antiaromatic Porphyrinoid 査読有り国際誌

Ito Tomohiro, Hayashi Yosuke, Shimizu Soji, Shin Ji-Young, Kobayashi Nagao, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 51 巻 ( 34 ) 頁： 8542 - 8545 2012年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Wiley

Small is beautiful: A ring-contracted sister of porphyrin, norcorrole, has been synthesized efficiently as a stable molecule by a nickel-templated strategy. The norcorrole complex is stable but exhibits a distinct antiaromatic character according to the Hückel rule. Oxidation of the norcorrole complex provides an aromatic oxacorrole complex.

DOI： 10.1002/anie.201204395

Intermolecular Oxidative Annulation of 2-Aminoanthracenes to Diazaacenes and Aza[7]helicenes 査読有り国際誌

Goto Kiyohiko, Yamaguchi Ryuichi, Hiroto Satoru, Ueno Hiroshi, Kawai Tsuyoshi, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 51 巻 ( 41 ) 頁： 10333 - 10336 2012年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Angewandte Chemie - International Edition

Which way to go: The product distribution in the efficient oxidation of 2-aminoanthracene derivatives to pyrazine- and pyrrole-fused bisanthracenes can be controlled by additives (see scheme; TFA=trifluoroacetic acid, DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone). The pyrrole-fused dimer can be regarded as an aza[7]helicene with a stable helical conformation. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/anie.201204863

Functionalization of a Simple Dithienylethene via Palladium-Catalyzed Regioselective Direct Arylation 査読有り国際誌

Kamiya Hiroki, Yanagisawa Shuichi, Hiroto Satoru, Itami Kenichiro, Shinokubo Hiroshi

ORGANIC LETTERS 13 巻 ( 24 ) 頁： 6394 - 6397 2011年12月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

The direct arylation on the thienyl groups of a diarylethene with various aryl iodides efficiently provided arylated dithienylethenes under palladium catalysis. Unsymmetrically substituted dithienylethenes were also synthesized by this protocol. This procedure allows a rapid access to a variety of aryl-substituted dithienylethenes from a single substrate of a simple dithienylethene. © 2011 American Chemical Society.

DOI： 10.1021/ol2026069

A Hexameric Porphyrin Triangle Constructed by Suzuki-Miyaura Cross-coupling Reaction 査読有り国際誌

Song Jianxin, Anabuki Shoma, Aratani Naoki, Shinokubo Hiroshi, Osuka Atsuhiro

CHEMISTRY LETTERS 40 巻 ( 9 ) 頁： 902 - 903 2011年9月

Synthetic Protocol for Diarylethenes through Suzuki-Miyaura Coupling 査読有り

Satoru Hiroto, Katsuya Suzuki, Hiroki Kamiya, and Hiroshi Shinokubo

Chem. Commun. 47 巻 ( 25 ) 頁： 7149-7151 2011年5月

Synthesis of Directly Connected BODIPY Oligomers through Suzuki-Miyaura Coupling 査読有り

Yosuke Hayashi, Shigeru Yamaguchi, Won Young Cha, Dongho Kim, and Hiroshi Shinokubo

Org. Lett. 13 巻 ( 12 ) 頁： 2992-2995 2011年5月

Iridium-Catalyzed Direct Tetraborylation of Perylene Bisimides 査読有り

Takuro Teraoka, Satoru Hiroto, and Hiroshi Shinokubo

Org. Lett. 13 巻 ( 10 ) 頁： 2532-2535 2011年4月

Metal-Mediated Synthesis of Antiaromatic Porphyrinoids from a BODIPY Precursor 査読有り

Takafumi Sakida, Shigeru Yamaguchi, and Hiroshi Shinokubo

Angew. Chem., Int. Ed. 50 巻 ( 10 ) 頁： 2280-2283 2011年2月

A beta-to-beta 2,5-Thienylene-Bridged Cyclic Porphyrin Tetramer: Its Rational Synthesis and 1:2 Binding Mode with C60 査読有り

Jianxin Song, Naoki Aratani, Hiroshi Shinokubo, and Atsuhiro Osuka

Chem. Sci. 2 巻 ( 4 ) 頁： 748-751 2011年1月

Peripherally Cyclometalated Iridium Complexes of Dipyridylporphyrin 査読有り

Keita Yoshida, Takumi Nakashima, Shigeru Yamaguchi, Atsuhiro Osuka and Hiroshi Shinokubo

Dalton Trans. 頁： in press 2011年

Synthesis of a Diimidazolylporphyrin Pincer Palladium Complex 査読有り

Jun Yamamoto, Tomohiro Shimizu, Shigeru Yamaguchi, Naoki Aratani, Hiroshi Shinokubo and Atsuhiro Osuka

J. Porphyrins Phthalocyanines 頁： in press 2011年

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