Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling

Yosuke Hayashi; Shigeru Yamaguchi; Won Young Cha; Dongho Kim; Hiroshi Shinokubo

doi:10.1021/ol200799u

Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling

Yosuke Hayashi, Shigeru Yamaguchi, Won Young Cha, Dongho Kim, Hiroshi Shinokubo

Department of Chemistry

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

146 Citations (Scopus)

Abstract

Treatment of a meso-arylboron dipyrrin (BODIPY) with NBS provides mono- and dibrominated BODIPYs at the 2- and 6-positions in excellent yields with high regioselectivity. Brominated products can be employed as a nice building block for the synthesis of a variety of BODIPY derivatives through Suzuki-Miyaura coupling. Because of a lack of substituents at the 1,3,5,7-positions, a directly β-β-linked BODIPY dimer exhibits a completely coplanar conformation of BODIPY units, offering effective π-conjugation.

Original language	English
Pages (from-to)	2992-2995
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	12
DOIs	https://doi.org/10.1021/ol200799u
Publication status	Published - 2011 Jun 17

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200799u

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title = "Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling",

abstract = "Treatment of a meso-arylboron dipyrrin (BODIPY) with NBS provides mono- and dibrominated BODIPYs at the 2- and 6-positions in excellent yields with high regioselectivity. Brominated products can be employed as a nice building block for the synthesis of a variety of BODIPY derivatives through Suzuki-Miyaura coupling. Because of a lack of substituents at the 1,3,5,7-positions, a directly β-β-linked BODIPY dimer exhibits a completely coplanar conformation of BODIPY units, offering effective π-conjugation.",

author = "Yosuke Hayashi and Shigeru Yamaguchi and Cha, {Won Young} and Dongho Kim and Hiroshi Shinokubo",

year = "2011",

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doi = "10.1021/ol200799u",

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journal = "Organic Letters",

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T1 - Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling

AU - Hayashi, Yosuke

AU - Yamaguchi, Shigeru

AU - Cha, Won Young

AU - Kim, Dongho

AU - Shinokubo, Hiroshi

PY - 2011/6/17

Y1 - 2011/6/17

N2 - Treatment of a meso-arylboron dipyrrin (BODIPY) with NBS provides mono- and dibrominated BODIPYs at the 2- and 6-positions in excellent yields with high regioselectivity. Brominated products can be employed as a nice building block for the synthesis of a variety of BODIPY derivatives through Suzuki-Miyaura coupling. Because of a lack of substituents at the 1,3,5,7-positions, a directly β-β-linked BODIPY dimer exhibits a completely coplanar conformation of BODIPY units, offering effective π-conjugation.

AB - Treatment of a meso-arylboron dipyrrin (BODIPY) with NBS provides mono- and dibrominated BODIPYs at the 2- and 6-positions in excellent yields with high regioselectivity. Brominated products can be employed as a nice building block for the synthesis of a variety of BODIPY derivatives through Suzuki-Miyaura coupling. Because of a lack of substituents at the 1,3,5,7-positions, a directly β-β-linked BODIPY dimer exhibits a completely coplanar conformation of BODIPY units, offering effective π-conjugation.

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JO - Organic Letters

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Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura coupling

Abstract

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