Planar chirality of twisted trans-azobenzene structure induced by chiral transfer from binaphthyls

Kazuto Takaishi; Atsuya Muranaka; Masuki Kawamoto; Masanobu Uchiyama

doi:10.1021/jo201578z

Planar chirality of twisted trans-azobenzene structure induced by chiral transfer from binaphthyls

Kazuto Takaishi, Atsuya Muranaka, Masuki Kawamoto, Masanobu Uchiyama

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

29 Citations (Scopus)

Abstract

The absolute configuration of a binaphthyl-azobenzene dyad 2b, which has a chiral axis and a chiral plane, was determined by comparing the experimental circular dichroism (CD) spectra with the theoretical CD spectra calculated by the time-dependent (TD)-DFT method. The CD signals of the trans-azobenzene moiety indicated that the two benzene rings of this moiety are twisted unidirectionally. It is suggested that these dyads with shorter linkers may be suitable for use as chiroptical switches.

Original language	English
Pages (from-to)	7623-7628
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	76
Issue number	18
DOIs	https://doi.org/10.1021/jo201578z
Publication status	Published - Sept 16 2011
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The absolute configuration of a binaphthyl-azobenzene dyad 2b, which has a chiral axis and a chiral plane, was determined by comparing the experimental circular dichroism (CD) spectra with the theoretical CD spectra calculated by the time-dependent (TD)-DFT method. The CD signals of the trans-azobenzene moiety indicated that the two benzene rings of this moiety are twisted unidirectionally. It is suggested that these dyads with shorter linkers may be suitable for use as chiroptical switches.",

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

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T1 - Planar chirality of twisted trans-azobenzene structure induced by chiral transfer from binaphthyls

AU - Takaishi, Kazuto

AU - Muranaka, Atsuya

AU - Kawamoto, Masuki

AU - Uchiyama, Masanobu

PY - 2011/9/16

Y1 - 2011/9/16

N2 - The absolute configuration of a binaphthyl-azobenzene dyad 2b, which has a chiral axis and a chiral plane, was determined by comparing the experimental circular dichroism (CD) spectra with the theoretical CD spectra calculated by the time-dependent (TD)-DFT method. The CD signals of the trans-azobenzene moiety indicated that the two benzene rings of this moiety are twisted unidirectionally. It is suggested that these dyads with shorter linkers may be suitable for use as chiroptical switches.

AB - The absolute configuration of a binaphthyl-azobenzene dyad 2b, which has a chiral axis and a chiral plane, was determined by comparing the experimental circular dichroism (CD) spectra with the theoretical CD spectra calculated by the time-dependent (TD)-DFT method. The CD signals of the trans-azobenzene moiety indicated that the two benzene rings of this moiety are twisted unidirectionally. It is suggested that these dyads with shorter linkers may be suitable for use as chiroptical switches.

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Planar chirality of twisted trans-azobenzene structure induced by chiral transfer from binaphthyls

Abstract

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