Conformational ordering of apolar chiral m-phenylene ethynylene oligomers

L. Brunsveld; R.B. Prince; E.W. Meijer; J.S. Moore

doi:10.1021/ol0056877

Conformational ordering of apolar chiral m-phenylene ethynylene oligomers

L. Brunsveld
, R.B. Prince
, E.W. Meijer
, J.S. Moore

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

69 Citations (Scopus)

Abstract

A series of m-phenylene ethynylene oligomers containing nonpolar, (S)-3,7-dimethyl-1-octanoxy side chains have been synthesized and studied. In apolar alkane solvents, oligomers of sufficient length (n > 10) were found to adopt a helical conformation with a large twist sense bias. In contrast, in chloroform the oligomers adopt a random coil conformation. Surprisingly, the strong twist sense bias was determined to be highly time dependent and is partially attributed to intermolecular aggregation.

Original language	English
Pages (from-to)	1525-1528
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	11
DOIs	https://doi.org/10.1021/ol0056877
Publication status	Published - 2000

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title = "Conformational ordering of apolar chiral m-phenylene ethynylene oligomers",

abstract = "A series of m-phenylene ethynylene oligomers containing nonpolar, (S)-3,7-dimethyl-1-octanoxy side chains have been synthesized and studied. In apolar alkane solvents, oligomers of sufficient length (n > 10) were found to adopt a helical conformation with a large twist sense bias. In contrast, in chloroform the oligomers adopt a random coil conformation. Surprisingly, the strong twist sense bias was determined to be highly time dependent and is partially attributed to intermolecular aggregation.",

author = "L. Brunsveld and R.B. Prince and E.W. Meijer and J.S. Moore",

year = "2000",

doi = "10.1021/ol0056877",

language = "English",

volume = "2",

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journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Conformational ordering of apolar chiral m-phenylene ethynylene oligomers

AU - Brunsveld, L.

AU - Prince, R.B.

AU - Meijer, E.W.

AU - Moore, J.S.

PY - 2000

Y1 - 2000

N2 - A series of m-phenylene ethynylene oligomers containing nonpolar, (S)-3,7-dimethyl-1-octanoxy side chains have been synthesized and studied. In apolar alkane solvents, oligomers of sufficient length (n > 10) were found to adopt a helical conformation with a large twist sense bias. In contrast, in chloroform the oligomers adopt a random coil conformation. Surprisingly, the strong twist sense bias was determined to be highly time dependent and is partially attributed to intermolecular aggregation.

AB - A series of m-phenylene ethynylene oligomers containing nonpolar, (S)-3,7-dimethyl-1-octanoxy side chains have been synthesized and studied. In apolar alkane solvents, oligomers of sufficient length (n > 10) were found to adopt a helical conformation with a large twist sense bias. In contrast, in chloroform the oligomers adopt a random coil conformation. Surprisingly, the strong twist sense bias was determined to be highly time dependent and is partially attributed to intermolecular aggregation.

U2 - 10.1021/ol0056877

DO - 10.1021/ol0056877

M3 - Article

SN - 1523-7060

VL - 2

SP - 1525

EP - 1528

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Conformational ordering of apolar chiral m-phenylene ethynylene oligomers

Abstract

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