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

Kota Yoshida; Wonhee Cha; Dongho Kim; Atsuhiro Osuka

doi:10.1002/anie.201612277

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

Kota Yoshida, Wonhee Cha, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

13 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 language	English
Pages (from-to)	2492-2496
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	9
DOIs	https://doi.org/10.1002/anie.201612277
Publication status	Published - 2017 Feb 20

Bibliographical note

Funding Information:
This work was supported by JSPS KAKENHI Grant Numbers 25220802 and 25620031. K.Y. acknowledges a JSPS Fellowship for young Scientists. The work at Yonsei University was supported by Global Research Laboratory (2013K1A1A2A02050183).

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201612277

Cite this

@article{e397c1b793d94e1daa960698915a10b8,

title = "Synthesis of Boron(III)-Coordinated Subchlorophins and Their Peripheral Modifications",

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.",

author = "Kota Yoshida and Wonhee Cha and Dongho Kim and Atsuhiro Osuka",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers 25220802 and 25620031. K.Y. acknowledges a JSPS Fellowship for young Scientists. The work at Yonsei University was supported by Global Research Laboratory (2013K1A1A2A02050183). Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = feb,

day = "20",

doi = "10.1002/anie.201612277",

language = "English",

volume = "56",

pages = "2492--2496",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "9",

}

TY - JOUR

T1 - Synthesis of Boron(III)-Coordinated Subchlorophins and Their Peripheral Modifications

AU - Yoshida, Kota

AU - Cha, Wonhee

AU - Kim, Dongho

AU - Osuka, Atsuhiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Numbers 25220802 and 25620031. K.Y. acknowledges a JSPS Fellowship for young Scientists. The work at Yonsei University was supported by Global Research Laboratory (2013K1A1A2A02050183). Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/2/20

Y1 - 2017/2/20

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85010377748&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85010377748&partnerID=8YFLogxK

U2 - 10.1002/anie.201612277

DO - 10.1002/anie.201612277

M3 - Article

C2 - 28112474

AN - SCOPUS:85010377748

SN - 1433-7851

VL - 56

SP - 2492

EP - 2496

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 9

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this