Subporphyrins with an axial B-C bond

Shun Saga; Shin Ya Hayashi; Kouta Yoshida; Eiji Tsurumaki; Pyosang Kim; Young Mo Sung; Jooyoung Sung; Takayuki Tanaka; Dongho Kim; Atsuhiro Osuka

doi:10.1002/chem.201302454

Subporphyrins with an axial B-C bond

Shun Saga, Shin Ya Hayashi, Kouta Yoshida, Eiji Tsurumaki, Pyosang Kim, Young Mo Sung, Jooyoung Sung, Takayuki Tanaka, Dongho Kim^*, Atsuhiro Osuka

^*Corresponding author for this work

Chemistry

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

32 Scopus citations

Abstract

Axial fabrications of subporphyrins have been conveniently accomplished by the reaction of B(methoxo)triphenylsubporphyrin with Grignard reagents such as aryl-, heteroaryl-, ferrocenyl-, β-styryl-, phenylethynyl-, and ethylmagnesium bromides. The axial groups thus introduced are not conjugated with the subporphyrin core. This situation leads to effective fluorescence quenching of subporphyrins when the axial group is strongly electron donating such as 4-dimethylaminophenyl and ferrocenyl groups.

Original language	English (US)
Pages (from-to)	11158-11161
Number of pages	4
Journal	Chemistry - A European Journal
Volume	19
Issue number	34
DOIs	https://doi.org/10.1002/chem.201302454
State	Published - Aug 19 2013

Keywords

Grignard reaction
boron-carbon bond
electron transfer
porphyrinoids
subporphyrins

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201302454

Cite this

@article{9cef852d0ea74bf2b49daa5ab66324cc,

title = "Subporphyrins with an axial B-C bond",

abstract = "Axial fabrications of subporphyrins have been conveniently accomplished by the reaction of B(methoxo)triphenylsubporphyrin with Grignard reagents such as aryl-, heteroaryl-, ferrocenyl-, β-styryl-, phenylethynyl-, and ethylmagnesium bromides. The axial groups thus introduced are not conjugated with the subporphyrin core. This situation leads to effective fluorescence quenching of subporphyrins when the axial group is strongly electron donating such as 4-dimethylaminophenyl and ferrocenyl groups.",

keywords = "Grignard reaction, boron-carbon bond, electron transfer, porphyrinoids, subporphyrins",

author = "Shun Saga and Hayashi, {Shin Ya} and Kouta Yoshida and Eiji Tsurumaki and Pyosang Kim and Sung, {Young Mo} and Jooyoung Sung and Takayuki Tanaka and Dongho Kim and Atsuhiro Osuka",

year = "2013",

month = aug,

day = "19",

doi = "10.1002/chem.201302454",

language = "English (US)",

volume = "19",

pages = "11158--11161",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "34",

}

TY - JOUR

T1 - Subporphyrins with an axial B-C bond

AU - Saga, Shun

AU - Hayashi, Shin Ya

AU - Yoshida, Kouta

AU - Tsurumaki, Eiji

AU - Kim, Pyosang

AU - Sung, Young Mo

AU - Sung, Jooyoung

AU - Tanaka, Takayuki

AU - Kim, Dongho

AU - Osuka, Atsuhiro

PY - 2013/8/19

Y1 - 2013/8/19

N2 - Axial fabrications of subporphyrins have been conveniently accomplished by the reaction of B(methoxo)triphenylsubporphyrin with Grignard reagents such as aryl-, heteroaryl-, ferrocenyl-, β-styryl-, phenylethynyl-, and ethylmagnesium bromides. The axial groups thus introduced are not conjugated with the subporphyrin core. This situation leads to effective fluorescence quenching of subporphyrins when the axial group is strongly electron donating such as 4-dimethylaminophenyl and ferrocenyl groups.

AB - Axial fabrications of subporphyrins have been conveniently accomplished by the reaction of B(methoxo)triphenylsubporphyrin with Grignard reagents such as aryl-, heteroaryl-, ferrocenyl-, β-styryl-, phenylethynyl-, and ethylmagnesium bromides. The axial groups thus introduced are not conjugated with the subporphyrin core. This situation leads to effective fluorescence quenching of subporphyrins when the axial group is strongly electron donating such as 4-dimethylaminophenyl and ferrocenyl groups.

KW - Grignard reaction

KW - boron-carbon bond

KW - electron transfer

KW - porphyrinoids

KW - subporphyrins

UR - http://www.scopus.com/inward/record.url?scp=84882243242&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84882243242&partnerID=8YFLogxK

U2 - 10.1002/chem.201302454

DO - 10.1002/chem.201302454

M3 - Article

C2 - 23857881

AN - SCOPUS:84882243242

SN - 0947-6539

VL - 19

SP - 11158

EP - 11161

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 34

ER -

Subporphyrins with an axial B-C bond

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this