Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Porphyrin Analogues That Consist of Indole, Benzofuran, and Benzothiophene Subunits Reviewed International journal

Shoichi Nakamura, Takeshi Kondo, Satoru Hiroto, Hiroshi Shinokubo

ASIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 2 ( 4 ) page： 312 - 319 2013.4

Functionalization of Hexa-peri-hexabenzocoronenes: Investigation of the Substituent Effects on a Superbenzene Reviewed International journal

Ryuichi Yamaguchi, Satoru Ito, Byung Sun Lee, Satoru Hiroto, Dongho Kim, Hiroshi Shinokubo

CHEMISTRY-AN ASIAN JOURNAL Vol. 8 ( 1 ) page： 178 - 190 2013.1

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

We have demonstrated that the iridium-catalyzed direct borylation of hexa-peri-hexabenzocoronene (HBC) enables regioselective introduction of boryl groups to the para-, ortho-, and meta-substituted HBCs in high yields. The boryl groups have been transformed into various functionalities such as hydroxy, cyano, ethynyl, and amino groups. We have elucidated that the substituents significantly influence the photophysical properties of HBCs to enhance fluorescence quantum yields. DFT calculations revealed that the origin of the substituent effect is the lift in degeneracy in the frontier orbitals by an interaction with electron-donating and electron-withdrawing substituents at the para- and ortho-positions. The change in molecular orbitals results in an increase of the transition probability from the S-0 -> S-1 states. In addition, the two-photon absorption cross-section values of para-substituted HBCs are significantly larger than those of ortho-and meta-substituted HBCs.

DOI： 10.1002/asia.201200723

Synthesis of highly distorted π-extended [2.2]metacyclophanes by intermolecular double oxidative coupling Reviewed International journal

Yutaro Koyama, Satoru Hiroto, Hiroshi Shinokubo

Angewandte Chemie - International Edition Vol. 52 ( 22 ) page： 5740 - 5743 2013

Language：Japanese Publishing type：Research paper (scientific journal)

A strained relationship: Oxidation of dihydroxy-substituted acenes provides face-to-face [2.2]metacyclophane-like dimers (see scheme
Ored, Si of iPr 3Si groupsblue). The products exhibited highly distorted structures caused by steric repulsion. UV/Vis and electrochemical analysis revealed that the HOMO-LUMO gap was decreased upon dimerization. Copyright © 2013 WILEY-VCH Verlag GmbH &amp
Co. KGaA, Weinheim.

DOI： 10.1002/anie.201301180

Carbolithiation of meso-aryl-substituted 5,15-diazaporphyrin selectively provides 3-alkylated diazachlorins Reviewed International journal

Ayaka Yamaji, Satoru Hiroto, Ji-Young Shin, Hiroshi Shinokubo

Chemical Communications Vol. 49 ( 44 ) page： 5064 - 5066 2013

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry

Treatment of meso-mesityl 5,15-diazaporphyrin with alkyllithiums in toluene at low temperature provided monoalkylated diazachlorins through highly regioselective nucleophilic addition at the β-position near the meso-nitrogen atom. © The Royal Society of Chemistry 2013.

DOI： 10.1039/c3cc41907j

Assembled structures of dipyrrins and their oligomers bridged by dioxy-boron moieties Reviewed International journal

Hiromitsu Maeda, Yuki Nishimura, Satoru Hiroto, Hiroshi Shinokubo

DALTON TRANSACTIONS Vol. 42 ( 45 ) page： 15885 - 15888 2013

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：ROYAL SOC CHEMISTRY

A linear arrangement of BODIPY dimers and trimers was transformed into boron-bridged box, ladder and cage structures on treatment with spacer units possessing multiple diol moieties.

DOI： 10.1039/c3dt50783a

meso-Thiaporphyrinoids Revisited: Missing of Sulfur by Small Metals Reviewed International journal

Hiroki Kamiya, Takeshi Kondo, Takafumi Sakida, Shigeru Yamaguchi, Hiroshi Shinokubo

CHEMISTRY-A EUROPEAN JOURNAL Vol. 18 ( 50 ) page： 16129 - 16135 2012.12

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

Facile synthesis of meso-aryl-substituted 5,15-dithiaporphyrins and 10-thiacorroles has been achieved by sulfidation of a,a'-dichlorodipyrrin metal complexes with sodium sulfide in DMF. Thiacorrole metal complexes exhibit distinct aromaticity due to 18?p-conjugation including the lone pair on sulfur, whereas dithiaporphyrins are nonaromatic judging from 1H NMR spectra, X-ray analysis, and absorption spectra. We have found that NiII and AlIII dithiaporphyrin complexes undergo smooth thermal sulfur extrusion reaction to give the corresponding thiacorrole complexes, whereas free base, ZnII, PdII, and PtII dithiaporphyrin complexes did not exhibit the similar reactivity. The DFT calculations have elucidated a reaction pathway involving an episulfide intermediate, which can explain the markedly different reactivity among dithiaporphyrin metal complexes.

DOI： 10.1002/chem.201203255

Synthesis of Oxygen-Substituted Hexa-peri-hexabenzocoronenes through Ir-Catalyzed Direct Borylation Reviewed International journal

Ryuichi Yamaguchi, Satoru Hiroto, Hiroshi Shinokubo

ORGANIC LETTERS Vol. 14 ( 10 ) page： 2472 - 2475 2012.5

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

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 pi-extended quinone.

DOI： 10.1021/ol300743f

Synthesis of Nickel(II) Azacorroles by Pd-Catalyzed Amination of a,a'-Dichlorodipyrrin NiII Complex and Their Properties Reviewed International journal

Miki Horie, Yosuke Hayashi, Shigeru Yamaguchi, Hiroshi Shinokubo

CHEMISTRY-A EUROPEAN JOURNAL Vol. 18 ( 19 ) page： 5919 - 5923 2012.5

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

Synthesis of nickel(II) complexes of meso-aryl-substituted azacorroles was performed by BuchwaldHartwig amination of a dipyrrin NiII complex with benzylamine through C?N and C?C coupling. The highly planar structure of NiII azacorroles was elucidated by X-ray diffraction analysis. 1H NMR analysis and nucleus independent chemical shift (NICS) calculation on NiII azacorrole revealed its distinct aromaticity with [17]triaza-annulene 18p conjugation. In addition, acylation of azacorrole selectively afforded N- and C-acylated azacorroles depending on the reaction conditions, showing the dual reactivity of azacorroles.

DOI： 10.1002/chem.201200485

Energy and Electron Transfer from Fluorescent Mesostructured Organosilica Framework to Guest Dyes Reviewed International journal

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

LANGMUIR Vol. 28 ( 8 ) page： 3987 - 3994 2012.2

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

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 Forster 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.

DOI： 10.1021/la204645k

Facile Synthesis of Biphenyl-Fused BODIPY and Its Property Reviewed International journal

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

ORGANIC LETTERS Vol. 14 ( 3 ) page： 866 - 869 2012.2

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

A biphenyl-fused BODIPY was synthesized through a facile oxidative cyclization of peripheral aryl-substituents at the beta-position of the BODIPY unit. The extended pi-system of the fused BODIPY induces near-infrared (NIR) absorption and strong pi-pi 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.

DOI： 10.1021/ol2033916

Ensemble and Single-Molecule Spectroscopic Study on Excitation Energy Transfer Processes in 1,3-Phenylene-Linked Perylenebisimide Oligomers Reviewed International journal

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

JOURNAL OF PHYSICAL CHEMISTRY B Vol. 116 ( 4 ) page： 1244 - 1255 2012.2

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

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-ylsubstituents 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 Forster-type energy hopping (EEH) times as compared with the EEH time constant (1.97 ps) calculated on the basis of the Forster 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.

DOI： 10.1021/jp208855u

Synthesis and oxidation of cyclic tetraindole Reviewed International journal

Shoichi Nakamura, Satoru Hiroto, Hiroshi Shinokubo

CHEMICAL SCIENCE Vol. 3 ( 2 ) page： 524 - 527 2012

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：ROYAL SOC CHEMISTRY

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.

DOI： 10.1039/c1sc00665g

Web of Science

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Mesoporous Organosilica Hybrids Consisting of Silica-Wrapped p-p Stacking Columns Reviewed International journal

Norihiro Mizoshita, Takao Tani, Hiroshi Shinokubo, Shinji Inagaki

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 51 ( 5 ) page： 1156 - 1160 2012

A meso-Spiro[Cyclopentadiene-Isoporphyrin] from a Phenylethynyl Porphyrin Platinum(II) Pincer Complex Reviewed International journal

Shoma Anabuki, Hiroshi Shinokubo, Naoki Aratani, Atsuhiro Osuka

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 51 ( 13 ) page： 3174 - 3177 2012

Oxidative Annulation of ss-Aminoporphyrins into Pyrazine-Fused Diporphyrins Reviewed International journal

Masanari Akita, Satoru Hiroto, Hiroshi Shinokubo

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 51 ( 12 ) page： 2894 - 2897 2012

Intermolecular Oxidative Annulation of 2-Aminoanthracenes to Diazaacenes and Aza[7]helicenes Reviewed International journal

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

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 51 ( 41 ) page： 10333 - 10336 2012

Gram-Scale Synthesis of Nickel(II) Norcorrole: The Smallest Antiaromatic Porphyrinoid Reviewed International journal

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

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 51 ( 34 ) page： 8542 - 8545 2012

Functionalization of a Simple Dithienylethene via Palladium-Catalyzed Regioselective Direct Arylation Reviewed International journal

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

ORGANIC LETTERS Vol. 13 ( 24 ) page： 6394 - 6397 2011.12

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

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.

DOI： 10.1021/ol2026069

A Hexameric Porphyrin Triangle Constructed by Suzuki-Miyaura Cross-coupling Reaction Reviewed International journal

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

CHEMISTRY LETTERS Vol. 40 ( 9 ) page： 902 - 903 2011.9

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：CHEMICAL SOC JAPAN

A meso-to-beta directly linked hexameric porphyrin triangle was synthesized by the Suzuki-Miyaura cross-coupling reaction via either one-pot or a stepwise route. Hexakis-zine(II) complex of the porphyrin triangle exhibits a split Soret band in the absorption spectrum, reflecting the effective exciton coupling over the whole molecule.

DOI： 10.1246/cl.2011.902

Web of Science

CiNii Research

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Synthetic Protocol for Diarylethenes through Suzuki-Miyaura Coupling Reviewed

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

Chem. Commun. Vol. 47 ( 25 ) page： 7149-7151 2011.5

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Papers - SHINOKUBO, Hiroshi