Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary hydrogen-bonded complexes with 4-benzamidoprolinol

Yuko Kawanami; Shin Ya Katsumata; Jun Ichi Mizoguchi; Masaki Nishijima; Gaku Fukuhara; Cheng Yang; Tadashi Mori; Yoshihisa Inoue

doi:10.1021/ol3023402

Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary hydrogen-bonded complexes with 4-benzamidoprolinol

Yuko Kawanami, Shin Ya Katsumata, Jun Ichi Mizoguchi, Masaki Nishijima, Gaku Fukuhara, Cheng Yang, Tadashi Mori, Yoshihisa Inoue

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

16 Citations (Scopus)

Abstract

Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/p-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.

Original language	English
Pages (from-to)	4962-4965
Number of pages	4
Journal	Organic letters
Volume	14
Issue number	18
DOIs	https://doi.org/10.1021/ol3023402
Publication status	Published - 2012 Sept 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary hydrogen-bonded complexes with 4-benzamidoprolinol",

abstract = "Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/p-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.",

author = "Yuko Kawanami and Katsumata, {Shin Ya} and Mizoguchi, {Jun Ichi} and Masaki Nishijima and Gaku Fukuhara and Cheng Yang and Tadashi Mori and Yoshihisa Inoue",

year = "2012",

month = sep,

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doi = "10.1021/ol3023402",

language = "English",

volume = "14",

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journal = "Organic Letters",

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T1 - Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary hydrogen-bonded complexes with 4-benzamidoprolinol

AU - Kawanami, Yuko

AU - Katsumata, Shin Ya

AU - Mizoguchi, Jun Ichi

AU - Nishijima, Masaki

AU - Fukuhara, Gaku

AU - Yang, Cheng

AU - Mori, Tadashi

AU - Inoue, Yoshihisa

PY - 2012/9/21

Y1 - 2012/9/21

N2 - Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/p-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.

AB - Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/p-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.

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Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary hydrogen-bonded complexes with 4-benzamidoprolinol

Abstract

ASJC Scopus subject areas

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