Unexpected chain length dependence on a chiral memory effect of 'meta-ethynylpyridine' oligomers

Shunsuke Takashima; Hajime Abe; Masahiko Inouye

doi:10.1016/j.tetasy.2013.03.019

Unexpected chain length dependence on a chiral memory effect of 'meta-ethynylpyridine' oligomers

Shunsuke Takashima, Hajime Abe^*, Masahiko Inouye

^*Corresponding author for this work

Member of the Board

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

17 Scopus citations

Abstract

The chain length dependence involving a chiral memory effect of 2,6-pyridylene ethynylene oligomers 'meta-ethynylpyridines' was investigated. The meta-ethynylpyridine oligomers associated with octyl β-d- glucopyranoside form a helical complex giving induced CD; the induced chirality could be memorized with the help of Cu(OTf)₂ as an additive. Contrary to our expectations, the study of the length dependence revealed that the 12-meric oligomer showed a more sustainable chiral memory effect than those observed in both of the shorter 6-meric and longer 18-meric oligomers.

Original language	English
Pages (from-to)	527-531
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	24
Issue number	9-10
DOIs	https://doi.org/10.1016/j.tetasy.2013.03.019
State	Published - 2013/05/31

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Unexpected chain length dependence on a chiral memory effect of 'meta-ethynylpyridine' oligomers",

abstract = "The chain length dependence involving a chiral memory effect of 2,6-pyridylene ethynylene oligomers 'meta-ethynylpyridines' was investigated. The meta-ethynylpyridine oligomers associated with octyl β-d- glucopyranoside form a helical complex giving induced CD; the induced chirality could be memorized with the help of Cu(OTf)2 as an additive. Contrary to our expectations, the study of the length dependence revealed that the 12-meric oligomer showed a more sustainable chiral memory effect than those observed in both of the shorter 6-meric and longer 18-meric oligomers.",

author = "Shunsuke Takashima and Hajime Abe and Masahiko Inouye",

note = "Funding Information: S.T. has been supported by the research fellowship of the Japan Society for the Promotion of Science. ",

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T1 - Unexpected chain length dependence on a chiral memory effect of 'meta-ethynylpyridine' oligomers

AU - Takashima, Shunsuke

AU - Abe, Hajime

AU - Inouye, Masahiko

N1 - Funding Information: S.T. has been supported by the research fellowship of the Japan Society for the Promotion of Science.

PY - 2013/5/31

Y1 - 2013/5/31

N2 - The chain length dependence involving a chiral memory effect of 2,6-pyridylene ethynylene oligomers 'meta-ethynylpyridines' was investigated. The meta-ethynylpyridine oligomers associated with octyl β-d- glucopyranoside form a helical complex giving induced CD; the induced chirality could be memorized with the help of Cu(OTf)2 as an additive. Contrary to our expectations, the study of the length dependence revealed that the 12-meric oligomer showed a more sustainable chiral memory effect than those observed in both of the shorter 6-meric and longer 18-meric oligomers.

AB - The chain length dependence involving a chiral memory effect of 2,6-pyridylene ethynylene oligomers 'meta-ethynylpyridines' was investigated. The meta-ethynylpyridine oligomers associated with octyl β-d- glucopyranoside form a helical complex giving induced CD; the induced chirality could be memorized with the help of Cu(OTf)2 as an additive. Contrary to our expectations, the study of the length dependence revealed that the 12-meric oligomer showed a more sustainable chiral memory effect than those observed in both of the shorter 6-meric and longer 18-meric oligomers.

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SN - 0957-4166

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JF - Tetrahedron Asymmetry

IS - 9-10

ER -

Unexpected chain length dependence on a chiral memory effect of 'meta-ethynylpyridine' oligomers

Abstract

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