Satoshi Ito

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Organization: Utsunomiya University

Department: Department of Applied Chemistry, Faculty of Engineering

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TOPICS

Inorganic Chemistry

Porphyrin

Chemicals
References

Synthesis of bicyclopyrroles with various substituents at the bridging positions

Co-reporter:Satoshi Ito, Marina Tobata, Minenari Asakura, Yasutaka Shinozaki, Yuuki Iwabe, Lisa Sakamoto, Shun-pei Ito, Makoto Roppongi, Toru Oba

Tetrahedron Letters 2017 Volume 58, Issue 43(Issue 43) pp:

Publication Date(Web):25 October 2017

DOI:10.1016/j.tetlet.2017.09.056

•We successfully synthesized novel bicyclopyrroles with various substituents.•Substituted bicyclopyrroles can be converted to isoindoles and their oligomers.•This method contributes to the development of new functional organic materials.Bicyclopyrroles are important synthetic equivalents of isoindoles, which are difficult to synthesize. Using bicyclopyrrole as a starting material, functional organic materials such as benzopyrromethene and benzoporphyrin can be synthesized. However, there are few reports on introducing substituents into bridging positions in bicyclopyrrole. By combining various reactions, we successfully obtained bicyclopyrroles with various substituents at the bridging positions.Download high-res image (104KB)Download full-size image

Synthesis of meso-substituted tetrabenzoporphyrin via selective meso-bromination of bicycloporphyrin

Co-reporter:Yutaro Ishii, Satoshi Ito, Takuya Komatsu, Hideyoshi Kimura, Daiki Uno, Akira Sasaki, Toru Oba

Tetrahedron Letters 2016 Volume 57(Issue 46) pp:5079-5083

Publication Date(Web):16 November 2016

DOI:10.1016/j.tetlet.2016.10.001

•meso-Brominated tetrabenzoporphyrins (BPs) were synthesized.•meso-Bromobicycloporphyrins were converted to various BPs via coupling reaction.•The devices based on meso-bromo CPs showed FET characteristics.Bicycloporphyrins (CPs) are important compounds as soluble precursors of tetrabenzoporphyrins (BPs). CPs can be converted to the corresponding BPs via selective bromination to meso-position, coupling reaction, and retro Diels–Alder reaction.

Synthesis of π-extended platinum porphyrins

Co-reporter:Satoshi Ito, Daishi Makihata, Yutaro Ishii, Yuki Saito, Toru Oba

Tetrahedron Letters 2015 Volume 56(Issue 50) pp:7043-7045

Publication Date(Web):16 December 2015

DOI:10.1016/j.tetlet.2015.11.018

We report the efficient synthesis of tetrabicycloporphyrin platinum under mild conditions (60 °C). The platinum complexes were heated under vacuum to give π-extended platinum porphyrins in 100% yield. The porphyrins are expected to have interesting properties such as high-quantum-efficiency near-IR phosphorescence and large absorptivity in the near-IR region.

Synthesis of [2,3]naphthoporphyrins using 4,9-dihydro-4,9-ethano-2H-benz[f]isoindole as a benz[f]isoindole equivalent

Co-reporter:Yutaro Ishii, Satoshi Ito, Yuki Saito, Daiki Uno, Toru Oba

Tetrahedron 2015 Volume 71(Issue 47) pp:8892-8898

Publication Date(Web):25 November 2015

DOI:10.1016/j.tet.2015.09.072

We report a new synthesis of 1,4-dihydro-1,4-ethanonaphthalene using 4,9-dihydro-4,9-ethano-2H-benz[f]isoindole as the equivalent of benz[f]isoindole, from p-benzoquinone as a starting material via the Diels–Alder reaction, Luche reduction, and dehydroxylation. We also report the synthesis of various new [2,3]naphthoporphyrin derivatives and their metal complexes.

Titanylation and vanadylation of highly π-conjugated porphyrins

Co-reporter:Satoshi Ito, Takahiro Ito, Daishi Makihata, Yutaro Ishii, Yuki Saito, Toru Oba

Tetrahedron Letters 2014 Volume 55(Issue 31) pp:4390-4394

Publication Date(Web):30 July 2014

DOI:10.1016/j.tetlet.2014.06.039

Synthesis of meso-fluorotetrabenzoporphyrins

Co-reporter:Satoshi Ito, Noriaki Terada, Komei Seino, Daishi Makihata, Akira Sasaki, Toru Oba

Tetrahedron Letters 2013 Volume 54(Issue 44) pp:5916-5919

Publication Date(Web):30 October 2013

DOI:10.1016/j.tetlet.2013.08.111

Fluorination of quadruply bicyclo[2.2.2]octadiene-fused porphyrin (CP) with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) occurred at the meso positions to give a mixture of various meso-fluorinated CPs, which were separated and then quantitatively transformed to the corresponding meso-fluorinated tetrafluorobenzoporphyrins (BPs) at 240 °C for 30 min. X-ray analysis of the mono-fluoro BPs revealed that the BP skeleton remained flat, which is crucial for retaining aggregation behavior similar to that of the parent BP, thus producing highly crystalline BP derivatives.

First Synthesis of meso-Chlorinated Tetrabenzoporphyrins

Co-reporter:Satoshi Ito;Le Thanh Phong;Takuya Komatsu;Nagisa Igarashi;Saika Otsubo;Yoshimasa Sakai;Akira Ohno;Shinji Aramaki;Yousuke Tanaka;Hidemitsu Uno;Toru Oba;Kazuhisa Hiratani

European Journal of Organic Chemistry 2009 Volume 2009( Issue 31) pp:5373-5382

Publication Date(Web):

DOI:10.1002/ejoc.200900601

Abstract

meso-Chlorinated bicyclo[2.2.2]octadiene-fused porphyrins 2 (Cl_nTBCODPs; n = 1–4) have been synthesized by chlorination of the free base TBCODP-H₂ (1-H₂) using N-chlorosuccinimide (NCS). The chlorinated derivatives were easily separated by column chromatography on silica gel to give 2-H₂ in good yields. This method for the chlorination of porphyrin using NCS is mild, safe, and economic compared with the established procedure for the meso-chlorination of porphyrins. We also discovered the unexpected meso-chlorination of the porphyrin with dichlorodicyanobenzoquinone (DDQ) by single-electron transfer. Cl_nTBCODPs 2 were converted into tetrabenzoporphyrins (Cl_nTBPs) 3 in 100 % yields by retro-Diels–Alder reaction. The derived compounds were characterized by NMR spectroscopy, UV/Vis spectrophotometry, cyclic voltammetry (CV), X-ray crystallography, and organic field-effect transistor (OFET) characteristics. The introduction of chlorine at the meso positions of the TBPs drastically changed their electronic and structural properties. The maxima of protonated Cl₄TBP-H₂ (3d-H₂; λ_max = 494, 649, and 707 nm) were redshifted by around 50–65 nm relative to those of protonated TBP-H₂ (λ_max = 431, 605, and 660 nm). The two Q-band maxima of the Cl₄TBP dication are similar to those of a tetraacenaphthoporphyrin dication (λ_max = 525, 646, and 702 nm), which has one of the most redshifted Q-bands.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Efficient synthesis of isoindoles using supercritical carbon dioxide

Co-reporter:Satoshi Ito, Masayuki Akaki, Yasutaka Shinozaki, Yuuki Iwabe, Masaru Furuya, Marina Tobata, Makoto Roppongi, Takafumi Sato, Naotsugu Itoh, Toru Oba

Tetrahedron Letters (29 March 2017) Volume 58(Issue 13) pp:

Publication Date(Web):29 March 2017

DOI:10.1016/j.tetlet.2017.02.055

•Bicyclopyrroles were converted to the corresponding isoindoles in supercritical CO2.•By adding ethylene gas as an oxygen scavenger, the isoindole yield was further improved.•This synthesis method provides a new methodology for the synthesis of isoindole derivatives.Bicyclopyrroles were efficiently converted to the corresponding isoindoles by a retro Diels-Alder reaction in supercritical carbon dioxide. By adding ethylene gas as an oxygen scavenger, the isoindole yield was further improved.

Extension of π-system of silylated porphyrin derivative for photodynamic therapy

Co-reporter:Hiroaki Horiuchi, Asumi Sakai, Shingo Akiyama, Remi Ikeda, Satoshi Ito, Masaru Furuya, Yuta Gomibuchi, Muneki Ichikawa, Toshitada Yoshihara, Seiji Tobita, Tetsuo Okutsu

Journal of Photochemistry and Photobiology A: Chemistry (15 April 2017) Volume 339() pp:19-24

Publication Date(Web):15 April 2017

DOI:10.1016/j.jphotochem.2017.02.015