Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Control of Conformation and Chirality of Nonplanar π-Conjugated Diporphyrins Using Substituents and Axial Ligands Reviewed International journal

Ito, S., Hiroto, S., Ousaka, N., Yashima, E., Shinokubo, H.

Chemistry - An Asian Journal Vol. 11 ( 6 ) page： 936 - 942 2016.3

Chemo- and Regioselective Reduction of 5,15-Diazaporphyrins Providing Antiaromatic Azaporphyrinoids Reviewed International journal

Yamaji, A., Tsurugi, H., Miyake, Y., Mashima, K., Shinokubo, H.

Chemistry - A European Journal Vol. 22 ( 12 ) page： 3956 - 3961 2016.3

Solubilization and Optical Tuning of Graphene Quantum Dots through Decarboxylative-Arylation Reviewed International journal

Oda Kazuma, Hiroto Satoru, SHinokubo Hiroshi

JSAP Annual Meetings Extended Abstracts Vol. 2016.1 ( 0 ) page： 3881 - 3881 2016.3

The synthesis of NiII and AlIII 10-azacorroles through coordination-induced cyclisation involving 1,2-migration Reviewed International journal

Omori, H., Hiroto, S., Shinokubo, H.

Chemical Communications Vol. 52 ( 17 ) page： 3540 - 3543 2016

NiII tetrahydronorcorroles: Antiaromatic porphyrinoids with saturated pyrrole units Reviewed International journal

Nozawa, R., Yamamoto, K., Hisaki, I., Shin, J.-Y., Shinokubo, H.

Chemical Communications Vol. 52 ( 44 ) page： 7106 - 7109 2016

Indolylindolinone: Easily accessible, tunable, and wide-range absorbing dyes Reviewed International journal

Shigeno, A., Matsuno, T., Hiroto, S., Shinokubo, H.

Chemistry Letters Vol. 44 ( 12 ) page： 1703 - 1705 2015.12

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

Dehydrative coupling between indoles and isatins provided indolylindolinones in good yields as novel dyes with wide-range absorption due to intramolecular charge-transfer interactions. The HOMO and LUMO levels of indolylindolinones could be manipulated individually by the introduction of substituents on the indole and isatin units, respectively. Indolylindolinones served as a bidentate ligand to Ni(II) and Cu(II) ions to provide stable metal complexes. Metal coordination induced large bathochromic shift of the lowest-energy absorption band to the near-infrared region.

DOI： 10.1246/cl.150815

Twisting of π-conjugated plane to one rotation Reviewed International journal

Hiroto S., Shinokubo H.

Kobunshi Vol. 64 ( 11 ) page： 713 - 714 2015.11

Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Kobunshi

We have established the facile and efficient protocol to synthesize distorted 71-conjugated molecules. Oxidation of amino-substituted porphyrins proceeded with high regioselectivity to produce pyrazine fused dimers. X-ray diffraction analysis revealed its highly twisted structure. Electrochemical and optical measurements indicated the twisting mostly influences on HOMO. The sequential use of our protocol has achieved the synthesis of unidirectionally twisted porphyrin tetramers efficiently. NMR analysis suggested that the racemization barrier of twisting increases on oligomerization. To the best of our knowledge, this is the first observation of a similar phenomenon observed in polymer science for twisted, jt-conjugated molecules. The present findings represent an important advance towards the long-term goal of preparing -conjugated molecular wires, whose properties can be fine-tuned through molecular twisting.

Scopus

A Stable Organic π-Radical of a Zinc(II)-Copper(I)-Zinc(II) Complex of Decaphyrin Reviewed International journal

Tanaka, Y., Yoneda, T., Furukawa, K., Koide, T., Mori, H., Tanaka, T., Shinokubo, H., Osuka, A.

Angewandte Chemie - International Edition Vol. 54 ( 37 ) page： 10908 - 10911 2015.9

Nitrogen-embedded buckybowl and its assembly with C[60] Reviewed International journal

Yokoi Hiroki, Hiraoka Yuya, Hiroto Satoru, Sakamaki Daisuke, Seki Shu, Shinokubo Hiroshi

Nature Communications Vol. 6 2015.9

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

Curved π-conjugated molecules have attracted considerable interest because of the unique properties originating from their curved π surface. However, the synthesis of such distorted molecules requires harsh conditions, which hamper easy access to heteroatom-containing curved π systems. Here we report the synthesis of a π-extended azacorannulene with nitrogen in its centre. The oxidation of 9-aminophenanthrene provides tetrabenzocarbazole, which is converted to the azabuckybowl through palladium-catalysed intramolecular coupling. The electron-donating nature and curved π surface of the azabuckybowl enable its tight association with C[60] in solution and solid states. High charge mobility is observed for the azabuckybowl/C[60] assembly. This compound may be of interest in the fields of curved π systems as fullerene hosts, anisotropic π donors and precursors to nitrogen-containing nanocarbon materials.

CiNii Research

Nitrogen-embedded buckybowl and its assembly with C<inf>60</inf> Reviewed International journal

Yokoi, H., Hiraoka, Y., Hiroto, S., Sakamaki, D., Seki, S., Shinokubo, H.

Nature Communications Vol. 6 page： 8215 2015.9

Regioselective Nucleophilic Functionalization of Antiaromatic Nickel(II) Norcorroles Reviewed International journal

Nozawa, R., Yamamoto, K., Shin, J.-Y., Hiroto, S., Shinokubo, H.

Angewandte Chemie - International Edition Vol. 54 ( 29 ) page： 8454 - 8457 2015.7

Synthesis of highly twisted and fully π-conjugated porphyrinic oligomers Reviewed International journal

Ito, S., Hiroto, S., Lee, S., Son, M., Hisaki, I., Yoshida, T., Kim, D., Kobayashi, N., Shinokubo, H.

Journal of the American Chemical Society Vol. 137 ( 1 ) page： 142 - 145 2015.1

Palladium-catalyzed [3+2] annulation of meso-bromoporphyrins with silylacetylenes and desilylation of 8a-silyl-7,8-dehydropurpurin Reviewed International journal

Fukui, N., Arai, S., Shinokubo, H., Yorimitsu, H., Osuka, A.

Heterocycles Vol. 90 ( 1 ) page： 252 - 260 2015.1

Synthesis of Novel Porphyrinoids from Dipyrrins Invited Reviewed International journal

Hiroshi Shinokubo

Chemical Science of Electron Systems page： 243 - 255 2015.1

Authorship：Lead author,　Last author,　Corresponding author Language：English Publishing type：Part of collection (book) Publisher：Springer Japan

Most syntheses of meso-substituted porphyrinoid rely on acid-catalyzed condensation of pyrrole segments with aldehyde units followed by oxidation. This standard procedure is convenient but generally is low yielding. However, modern synthetic methodologies would offer an expeditious route to several intriguing porphyrinoids. In particular, the metal template strategy using dipyrrin metal complexes is effective to construct porphyrin-like cyclic π-conjugated systems, which are otherwise difficult to access by the conventional methodology.

DOI： 10.1007/978-4-431-55357-1_14

Scopus

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Diversity-oriented synthesis of tetrathia[8]circulenes by sequential C-H borylation and annulation Reviewed International journal

Kato, S., Serizawa, Y., Sakamaki, D., Seki, S., Miyake, Y., Shinokubo, H.

Chemical Communications Vol. 51 ( 95 ) page： 16944 - 16947 2015

Macrocyclic dipyrrin dimer bridged by ethylene and dioxyphenylene linkers Reviewed International journal

Ji-Young Shin, Satoru Hiroto, Hiroshi Shinokubo

Journal of Porphyrins and Phthalocyanines Vol. 19 ( 1-3 ) page： 135 - 139 2015

Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene Reviewed International journal

Matsuno, T., Koyama, Y., Hiroto, S., Kumar, J., Kawai, T., Shinokubo, H.

Chemical Communications Vol. 51 ( 22 ) page： 4607 - 4610 2015

A 3-pyridyl-5,15-diazaporphyrin nickel(II) complex as a bidentate metalloligand for transition metals Reviewed International journal

Yamaji, A., Shin, J.-Y., Miyake, Y., Shinokubo, H.

Angewandte Chemie - International Edition Vol. 53 ( 50 ) page： 13924 - 13927 2014.12

Synthesis of curved hexa-peri-hexabenzocoronenes Reviewed International journal

Yamaguchi, R., Hiroto, S., Shinokubo, H.

Chemistry Letters Vol. 43 ( 10 ) page： 1637 - 1639 2014.10

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

Halogenation and phenylthiolation of hexabenzocoronenetetraone were performed. We found that introduction of substituents at the fjord regions induced substantial curvature of the hexabenzocoronene (HBC) plane through steric repulsion between the substituents and proximal hydrogen atoms. This method allows construction of curved HBC derivatives, which would allow formation of novel supramolecular structures.

DOI： 10.1246/cl.140577

Regioselective double cyclization of 5,15-bis(trimethylsilylethynyl)porphyrin to produce di(oxoethano)porphyrin Reviewed International journal

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

Chemistry Letters Vol. 43 ( 9 ) page： 1444 - 1446 2014.9

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

Treatment of bis(trimethylsilylethynyl)porphyrin with strong acids afforded doubly oxoethano-fused porphyrin with perfect regioselectivity. The oxoethano-fused porphyrin was more electron deficient than meso-acetylporphyrin because of the coplanar orientation of the carbonyl groups to the porphyrin π system.

DOI： 10.1246/cl.140470

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Papers - SHINOKUBO, Hiroshi