Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Facile synthesis of nitrogen-containing polycyclic aromatic hydrocarbons from perylene bisimides Reviewed International journal

Ito, S., Hiroto, S., Shinokubo, H.

Chemistry Letters Vol. 43 ( 8 ) page： 1309 - 1311 2014.8

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：The Chemical Society of Japan

We have developed a facile procedure for the synthesis of π-extended fluorubins from perylene bisimides. Iridium-catalyzed direct borylation, the Suzuki–Miyaura cross-coupling, and an acid-condensation sequence afforded π-extended fluorubins 1 in moderate yields. X-ray diffraction analysis revealed a planar structure of 1. In addition, optical analysis and DFT calculations indicated the presence of intramolecular charge-transfer interactions in 1c.

DOI： 10.1246/cl.140330

Synthesis of diazo-bridged bodipy dimer and tetramer by oxidative coupling of β-amino-substituted BODIPYs Reviewed International journal

Yokoi, H., Hiroto, S., Shinokubo, H.

Organic Letters Vol. 16 ( 11 ) page： 3004 - 3007 2014.6

Photodynamics of [26]- and [28]Hexaphyrin-Bodipy Hybrids Reviewed International journal

Ji-Young Shin, Kilsuk Kim, Jong Min Lim, Takayuki Tanaka, Dongho Kim, Kimoon Kim, Hiroshi Shinokubo, Atsuhiro Osuka

CHEMISTRY-A EUROPEAN JOURNAL Vol. 20 ( 16 ) page： 4574 - 4582 2014.4

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

A set of hybrids having gradual variation in distances between hexaphyrin and bodipy moieties, given by uses of phenylene, biphenylene, and triphenyelene bridges was prepared. Efficient PET processes from bodipy (donor) to [26]- or [28]hexaphyrin (acceptor) were successfully observed, where the PET speed was controlled by intramolecular distances between the donor and the acceptor. UV irradiation at 515nm raised a band corresponding to the bodipy absorption. As the time delayed, the bodipy bands decreased and new absorption bands at 615 and 580nm corresponding to respective absorption bands of [28]- and [26]-hybrids gradually appeared. Whereas the femtosecond transient absorption spectra of [28]/[26]-hybrids having terphenylene bridges completely showed energy transfers from bodipy to hexaphyrin, irradiation of the hybrids using 615 and 580nm pulses did not induce opposite ways of the PET process. On the basis of enlarged center-to-center-distances of [26]-hybrids than those of [28]-hybrids, the set of [26]-hybrids resulted in slow decay/rise processes. PET parameters obtained with the experiments were fairly consistent with the PET parameters calculated.

DOI： 10.1002/chem.201400315

Silylethynyl substituents as porphyrin protecting groups for solubilization and selectivity control Reviewed International journal

Oda, K., Akita, M., Hiroto, S., Shinokubo, H.

Organic Letters Vol. 16 ( 6 ) page： 1818 - 1821 2014.3

An antiaromatic electrode-active material enabling high capacity and stable performance of rechargeable batteries Reviewed International journal

Shin, J.-Y., Yamada, T., Yoshikawa, H., Awaga, K., Shinokubo, H.

Angewandte Chemie - International Edition Vol. 53 ( 12 ) page： 3096 - 3101 2014.3

Synthesis of Novel Porphyrinoids through Organometallic Means Reviewed International journal

Shinokubo, H.

Journal of Synthetic Organic Chemistry Japan Vol. 72 ( 2 ) page： 149 - 157 2014.2

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：The Society of Synthetic Organic Chemistry, Japan

Porphyrin is a representative functional molecule, which consists of four pyrrole units linked by four carbon atoms with an 18π aromatic character. Most of porphyrin syntheses rely on acid-catalyzed condensation of pyrrole with aldehydes followed by oxidation, which are low-yielding in many cases. To establish more effective porphyrin synthesis, we have devoted our effort to combine porphyrin chemistry and modern organic synthesis through transition metal-mediated reactions. In this article, we focus on synthesis of novel porphyrin analogues through coupling of dipyrrin precursors. The metal-templated strategy using dipyrrin metal complexes was found to be quite efficient to construct porphyrin-like cyclic π-conjugated systems consisting of the dipyrrin unit, which exhibit intriguing optical and electronic properties.

DOI： 10.5059/yukigoseikyokaishi.72.149

有機金属化学的手法による新規ポルフィリン類縁体の合成 Reviewed International journal

忍久保洋

有機合成化学協会誌 = Journal of synthetic organic chemistry, Japan Vol. 72 ( 2 ) page： 149 - 157 2014.2

Near-IR absorbing nickel(II) porphyrinoids prepared by regioselective insertion of silylenes into antiaromatic nickel(II) norcorrole International coauthorship International journal

Fukuoka, T., Uchida, K., Sung, Y.M., Shin, J.-Y., Ishida, S., Lim, J.M., Hiroto, S., Furukawa, K., Kim, D., Iwamoto, T., Shinokubo, H.

Angewandte Chemie - International Edition Vol. 126 ( 6 ) page： 1532 - 1535 2014.1

Transition metal catalyzed borylation of functional π-systems Reviewed International journal

Shinokubo, H.

Proceedings of the Japan Academy Series B: Physical and Biological Sciences Vol. 90 ( 1 ) page： 1 - 11 2014.1

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：The Japan Academy

Borylated functional π-systems are useful building blocks to enable efficient synthesis of novel molecular architectures with beautiful structures, intriguing properties and unique functions. Introduction of boronic ester substituents to a variety of extended π-systems can be achieved through either iridium-catalyzed direct C–H borylation or the two-step procedure via electrophilic halogenation followed by palladium-catalyzed borylation. This review article focuses on our recent progress on borylation of large π-conjugated systems such as porphyrins, perylene bisimides, hexabenzocoronenes and dipyrrins.

DOI： 10.2183/pjab.90.1

Oxidation of 2-amino-substituted BODIPYs providing pyrazine-fused BODIPY trimers Reviewed International journal

Yokoi, H., Wachi, N., Hiroto, S., Shinokubo, H.

Chemical Communications Vol. 50 ( 21 ) page： 2715 - 2717 2014

Synthesis, reactivity and property of 5,15-dithiaporphyrin copper(II) complex Reviewed International journal

Wachi, N., Kondo, T., Ito, S., Hiroto, S., Shin, J.-Y., Shinokubo, H.

Journal of Porphyrins and Phthalocyanines Vol. 18 ( 8-9 ) page： 675 - 678 2014

Selective Synthesis of a [32]Octaphyrin(1.0.1.0.1.0.1.0) Bis(palladium) Complex by a Metal-Templated Strategy Reviewed International journal

Hiromitsu Kido, Ji-Young Shin, Hiroshi Shinokubo

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 52 ( 51 ) page： 13727 - 13730 2013.12

Selective Synthesis of a [32]Octaphyrin(1.0.1.0.1.0.1.0) Bis(palladium) Complex by a Metal‐Templated Strategy International journal

Hiromitsu Kido, Ji‐Young Shin, Hiroshi Shinokubo

Angewandte Chemie Vol. 125 ( 51 ) page： 13972 - 13975 2013.10

Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley

A shapely figure: A [32]octaphyrin(1.0.1.0.1.0.1.0) bis[palladium(II)] complex was selectively obtained through a metal-templated intermolecular homocoupling of a α,α'-dibromodipyrrin palladium(II) complex without formation the norcorrole. The weak antiaromatic character of the figure-eight [32]octaphyrin(1.0.1.0.1.0.1.0) system has been elucidated by spectroscopic measurements and DFT calculations.

DOI： 10.1002/ange.201306905

PubMed

CiNii Research

Synthesis of Pyridine-Fused Perylene Imides with an Amidine Moiety for Hydrogen Bonding Reviewed International journal

Satoru Ito, Satoru Hiroto, Hiroshi Shinokubo

ORGANIC LETTERS Vol. 15 ( 12 ) page： 3110 - 3113 2013.6

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

Pyridine-fused perylene tetracarboxylic acid bisimides (PBIs) were synthesized via Suzuki-Miyaura coupling and acid condensation. The fused PBIs with electron-donating substituents exhibited an intramolecular charge transfer Interaction. One of the N-alkyl substituents was selectively removed with BBr3 to create an amidine guest binding site. A hydrogen bonding Interaction with pentafluorobenzoic acid changed the absorption spectra and enhanced fluorescence.

DOI： 10.1021/ol401316q

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

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Papers - SHINOKUBO, Hiroshi