Synthesis of Boron(III)-Coordinated Subchlorophins and Their Peripheral Modifications

Kota Yoshida, Wonhee Cha, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A pyrrole-cleaving modification to transform boron(III) meso-triphenylsubporphyrin into boron(III) meso-triphenylsubchlorophin has been developed. Boron(III) subchlorophins thus synthesized show absorption and fluorescence spectra that are roughly similar to those of boron(III) subchlorins, but B-methoxy boron(III) subchlorophin showed considerably intensified fluorescence and a small Stokes shift. Peripheral modification reactions of B-phenyl boron(III) subchlorophin such as regioselective nitration with Cu(NO3)2⋅3 H2O, ipso-substitution reactions of boron(III) α-nitrosubchlorophin with CsF and CsCl, and Pd-catalyzed cross-coupling reactions of boron(III) α-chlorosubchlorophin with arylacetylenes, have been also explored to tune the optical properties of subchlorophins.

Original languageEnglish
Pages (from-to)2492-2496
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number9
DOIs
Publication statusPublished - 2017 Jan 1

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Boron
Fluorescence
Nitration
Pyrroles
Substitution reactions
Optical properties

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Yoshida, Kota ; Cha, Wonhee ; Kim, Dongho ; Osuka, Atsuhiro. / Synthesis of Boron(III)-Coordinated Subchlorophins and Their Peripheral Modifications. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 9. pp. 2492-2496.
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Synthesis of Boron(III)-Coordinated Subchlorophins and Their Peripheral Modifications. / Yoshida, Kota; Cha, Wonhee; Kim, Dongho; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 56, No. 9, 01.01.2017, p. 2492-2496.

Research output: Contribution to journalArticle

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AB - A pyrrole-cleaving modification to transform boron(III) meso-triphenylsubporphyrin into boron(III) meso-triphenylsubchlorophin has been developed. Boron(III) subchlorophins thus synthesized show absorption and fluorescence spectra that are roughly similar to those of boron(III) subchlorins, but B-methoxy boron(III) subchlorophin showed considerably intensified fluorescence and a small Stokes shift. Peripheral modification reactions of B-phenyl boron(III) subchlorophin such as regioselective nitration with Cu(NO3)2⋅3 H2O, ipso-substitution reactions of boron(III) α-nitrosubchlorophin with CsF and CsCl, and Pd-catalyzed cross-coupling reactions of boron(III) α-chlorosubchlorophin with arylacetylenes, have been also explored to tune the optical properties of subchlorophins.

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