Synthesis of carbazole-based selenaporphyrin via annulation

Motoki Masuda; Chihiro Maeda; Naoki Yoshioka

doi:10.1021/ol303392g

Synthesis of carbazole-based selenaporphyrin via annulation

Motoki Masuda, Chihiro Maeda, Naoki Yoshioka

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

34 Citations (Scopus)

Abstract

Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer 1, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer 3, while annulation reaction of 1 with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer 5a. Oxidation of isophlorin 5a afforded carbazole-based selenaporphyrin 5b, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region.

Original language	English
Pages (from-to)	578-581
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	3
DOIs	https://doi.org/10.1021/ol303392g
Publication status	Published - Feb 1 2013
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol303392g

Cite this

@article{e68eae1cf4dc43d795ae0fdd531f485c,

title = "Synthesis of carbazole-based selenaporphyrin via annulation",

abstract = "Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer 1, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer 3, while annulation reaction of 1 with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer 5a. Oxidation of isophlorin 5a afforded carbazole-based selenaporphyrin 5b, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region.",

author = "Motoki Masuda and Chihiro Maeda and Naoki Yoshioka",

year = "2013",

month = feb,

day = "1",

doi = "10.1021/ol303392g",

language = "English",

volume = "15",

pages = "578--581",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - Synthesis of carbazole-based selenaporphyrin via annulation

AU - Masuda, Motoki

AU - Maeda, Chihiro

AU - Yoshioka, Naoki

PY - 2013/2/1

Y1 - 2013/2/1

N2 - Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer 1, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer 3, while annulation reaction of 1 with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer 5a. Oxidation of isophlorin 5a afforded carbazole-based selenaporphyrin 5b, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region.

AB - Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer 1, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer 3, while annulation reaction of 1 with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer 5a. Oxidation of isophlorin 5a afforded carbazole-based selenaporphyrin 5b, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region.

UR - http://www.scopus.com/inward/record.url?scp=84873376569&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84873376569&partnerID=8YFLogxK

U2 - 10.1021/ol303392g

DO - 10.1021/ol303392g

M3 - Article

C2 - 23343402

AN - SCOPUS:84873376569

SN - 1523-7060

VL - 15

SP - 578

EP - 581

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Synthesis of carbazole-based selenaporphyrin via annulation

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this