Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads

Kazuto Takaishi; Jun Suzuki; Tatsuya Yabe; Hikaru Asano; Michihiro Nishikawa; Daisuke Hashizume; Atsuya Muranaka; Masanobu Uchiyama; Akihiro Yokoyama

doi:10.1021/acs.orglett.5b02041

Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads

Kazuto Takaishi, Jun Suzuki, Tatsuya Yabe, Hikaru Asano, Michihiro Nishikawa, Daisuke Hashizume, Atsuya Muranaka, Masanobu Uchiyama, Akihiro Yokoyama

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

10 Citations (Scopus)

Abstract

An axially chiral binaphthyl-bipyridyl cyclic dyad in which the two units are connected by short -CH₂O- linkers was synthesized. Experimental and theoretical analyses indicate that the (R)-binaphthyl unit in the dyad induces (R)-chirality in the bipyridyl unit, both in the solid state and in solution. It is shown that vibrational circular dichroism (VCD) is useful to determine the twisting pattern of 2,2′-bipyridyl compounds. The dyad shows crystallization-induced emission enhancement (CIEE).

Original language	English
Pages (from-to)	4098-4101
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.5b02041
Publication status	Published - Aug 12 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads",

abstract = "An axially chiral binaphthyl-bipyridyl cyclic dyad in which the two units are connected by short -CH2O- linkers was synthesized. Experimental and theoretical analyses indicate that the (R)-binaphthyl unit in the dyad induces (R)-chirality in the bipyridyl unit, both in the solid state and in solution. It is shown that vibrational circular dichroism (VCD) is useful to determine the twisting pattern of 2,2′-bipyridyl compounds. The dyad shows crystallization-induced emission enhancement (CIEE).",

author = "Kazuto Takaishi and Jun Suzuki and Tatsuya Yabe and Hikaru Asano and Michihiro Nishikawa and Daisuke Hashizume and Atsuya Muranaka and Masanobu Uchiyama and Akihiro Yokoyama",

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doi = "10.1021/acs.orglett.5b02041",

language = "English",

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T1 - Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads

AU - Takaishi, Kazuto

AU - Suzuki, Jun

AU - Yabe, Tatsuya

AU - Asano, Hikaru

AU - Nishikawa, Michihiro

AU - Hashizume, Daisuke

AU - Muranaka, Atsuya

AU - Uchiyama, Masanobu

AU - Yokoyama, Akihiro

PY - 2015/8/12

Y1 - 2015/8/12

N2 - An axially chiral binaphthyl-bipyridyl cyclic dyad in which the two units are connected by short -CH2O- linkers was synthesized. Experimental and theoretical analyses indicate that the (R)-binaphthyl unit in the dyad induces (R)-chirality in the bipyridyl unit, both in the solid state and in solution. It is shown that vibrational circular dichroism (VCD) is useful to determine the twisting pattern of 2,2′-bipyridyl compounds. The dyad shows crystallization-induced emission enhancement (CIEE).

AB - An axially chiral binaphthyl-bipyridyl cyclic dyad in which the two units are connected by short -CH2O- linkers was synthesized. Experimental and theoretical analyses indicate that the (R)-binaphthyl unit in the dyad induces (R)-chirality in the bipyridyl unit, both in the solid state and in solution. It is shown that vibrational circular dichroism (VCD) is useful to determine the twisting pattern of 2,2′-bipyridyl compounds. The dyad shows crystallization-induced emission enhancement (CIEE).

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JO - Organic Letters

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Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads

Abstract

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