Photoinversion of cisoid/transoid binaphthyls

Kazuto Takaishi; Atsuya Muranaka; Masuki Kawamoto; Masanobu Uchiyama

doi:10.1021/ol203053q

Photoinversion of cisoid/transoid binaphthyls

Kazuto Takaishi, Atsuya Muranaka, Masuki Kawamoto, Masanobu Uchiyama

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

22 Citations (Scopus)

Abstract

Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene induces a cisoid-binaphthyl structure.

Original language	English
Pages (from-to)	276-279
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	1
DOIs	https://doi.org/10.1021/ol203053q
Publication status	Published - Jan 6 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Photoinversion of cisoid/transoid binaphthyls",

abstract = "Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene induces a cisoid-binaphthyl structure.",

author = "Kazuto Takaishi and Atsuya Muranaka and Masuki Kawamoto and Masanobu Uchiyama",

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AU - Takaishi, Kazuto

AU - Muranaka, Atsuya

AU - Kawamoto, Masuki

AU - Uchiyama, Masanobu

PY - 2012/1/6

Y1 - 2012/1/6

N2 - Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene induces a cisoid-binaphthyl structure.

AB - Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene induces a cisoid-binaphthyl structure.

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Photoinversion of cisoid/transoid binaphthyls

Abstract

ASJC Scopus subject areas

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