Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Stacked antiaromatic porphyrins Reviewed International journal

Nozawa, R., Tanaka, H., Cha, W.-Y., Hong, Y., Hisaki, I., Shimizu, S., Shin, J.-Y., Kowalczyk, T., Irle, S., Kim, D., Shinokubo, H.

Nature Communications Vol. 7 page： 13620 2016.11

Reversible Carbon–Carbon Bond Breaking and Spin Equilibria in Bis(pyrimidinenorcorrole) Reviewed International journal

Liu, B., Yoshida, T., Li, X., Stępień, M., Shinokubo, H., Chmielewski, P.J.

Angewandte Chemie - International Edition Vol. 55 ( 42 ) page： 13142 - 13146 2016.10

Syntheses and Properties of Antiaromatic Porphyrinoids Reviewed International journal

Satoru Hiroto, Hiroshi Shinokubo

Handbook of Porphyrin Science (Volumes 36 – 40) 2016.7

β-to-β 2,5-Pyrrolylene-Linked Cyclic Porphyrin Oligomers Reviewed International journal

Rao, Y., Kim, J.O., Kim, W., Zhong, G., Yin, B., Zhou, M., Shinokubo, H., Aratani, N., Tanaka, T., Liu, S., Osuka, A., Kim, D., Song, J.

Chemistry - A European Journal Vol. 22 ( 26 ) page： 8801 - 8804 2016.6

Synthesis of Free-Base 10-Azacorroles Reviewed International journal

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

Organic Letters Vol. 18 ( 12 ) page： 2978 - 2981 2016.6

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

A novel synthetic protocol has been developed for free-base 10-azacorroles. Ni(0)-mediated homocoupling of nitrogen-bridged bisdipyrrin Zn(II) complexes afforded a series of free-base 5,15-diaryl-10-azacorroles in good yields. Pd(II) and Cu(II) complexes have been prepared through metalation of free-base 10-azacorroles. Optical and electrochemical properties of 10-azacorrole metal complexes can be tuned by meso-aryl substituents and central metals. Cyclic voltammetry and theoretical calculations elucidated that the central metals of 10-azacorroles significantly affected their electronic properties.

DOI： 10.1021/acs.orglett.6b01323

Fully-substituted 1,3-butadienes as π-conjugated linkers between pyrenes Reviewed International journal

Oda, K., Hiroto, S., Sakamaki, D., Seki, S., Shinokubo, H.

Chemistry Letters Vol. 45 ( 4 ) page： 403 - 405 2016.4

Authorship：Last author,　Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：The Chemical Society of Japan

Pyrenyl-substituted 1,3-butadienes bearing alkyl and aryl groups have been synthesized by palladium-catalyzed addition of 2-borylpyrene to internal alkynes. On UV irradiation, 1-pyrenylbutadienes undergo photochromism in solution. In the solid state, 1-pyrenyl-1,2,3,4-tetraaryl-1,3-butadiene exhibits red-shifted and broad emission as compared with the alkylated butadiene. The charge-carrier mobility of 1-pyrenyl-1,2,3,4-tetraalkyl-1,3-butadiene is higher than that of the arylated butadiene.

DOI： 10.1246/cl.151181

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

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Papers - SHINOKUBO, Hiroshi