pi-Conjugated oligomers and polymers with a self-assembled ladder-like structure

D.A.P. Delnoye; R.P. Sijbesma; J.A.J.M. Vekemans; E.W. Meijer

doi:10.1021/ja9614171

pi-Conjugated oligomers and polymers with a self-assembled ladder-like structure

D.A.P. Delnoye, R.P. Sijbesma, J.A.J.M. Vekemans, E.W. Meijer

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Abstract

A series of alternating polymers and well-defined oligomers, composed of 2,5-linked pyrazines and N,N'-diacylated phenylene-1,4-diamines were prepd. using the Stille cross-coupling. The presence of N-hydrogen bond acceptors and N-hydrogen bond donors in adjacent units induces intramol. hydrogen bonding and hence leads to spontaneous formation of a ladder-type structure in which the arylene units tend to become coplanar. Self-assembly of the ladder structure in soln. is convincingly demonstrated by NRM- and IR-spectroscopy. The acylation of the ortho-amine functionalities with lipophilic groups leads to strong hydrogen bonding and improve soly. These large ortho-substituents do not disturb the p-delocalization of the system

Original language	English
Pages (from-to)	8717-8718
Journal	Journal of the American Chemical Society
Volume	118
Issue number	36
DOIs	https://doi.org/10.1021/ja9614171
Publication status	Published - 1996

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title = "pi-Conjugated oligomers and polymers with a self-assembled ladder-like structure",

abstract = "A series of alternating polymers and well-defined oligomers, composed of 2,5-linked pyrazines and N,N'-diacylated phenylene-1,4-diamines were prepd. using the Stille cross-coupling. The presence of N-hydrogen bond acceptors and N-hydrogen bond donors in adjacent units induces intramol. hydrogen bonding and hence leads to spontaneous formation of a ladder-type structure in which the arylene units tend to become coplanar. Self-assembly of the ladder structure in soln. is convincingly demonstrated by NRM- and IR-spectroscopy. The acylation of the ortho-amine functionalities with lipophilic groups leads to strong hydrogen bonding and improve soly. These large ortho-substituents do not disturb the p-delocalization of the system",

author = "D.A.P. Delnoye and R.P. Sijbesma and J.A.J.M. Vekemans and E.W. Meijer",

year = "1996",

doi = "10.1021/ja9614171",

language = "English",

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T1 - pi-Conjugated oligomers and polymers with a self-assembled ladder-like structure

AU - Delnoye, D.A.P.

AU - Sijbesma, R.P.

AU - Vekemans, J.A.J.M.

AU - Meijer, E.W.

PY - 1996

Y1 - 1996

N2 - A series of alternating polymers and well-defined oligomers, composed of 2,5-linked pyrazines and N,N'-diacylated phenylene-1,4-diamines were prepd. using the Stille cross-coupling. The presence of N-hydrogen bond acceptors and N-hydrogen bond donors in adjacent units induces intramol. hydrogen bonding and hence leads to spontaneous formation of a ladder-type structure in which the arylene units tend to become coplanar. Self-assembly of the ladder structure in soln. is convincingly demonstrated by NRM- and IR-spectroscopy. The acylation of the ortho-amine functionalities with lipophilic groups leads to strong hydrogen bonding and improve soly. These large ortho-substituents do not disturb the p-delocalization of the system

AB - A series of alternating polymers and well-defined oligomers, composed of 2,5-linked pyrazines and N,N'-diacylated phenylene-1,4-diamines were prepd. using the Stille cross-coupling. The presence of N-hydrogen bond acceptors and N-hydrogen bond donors in adjacent units induces intramol. hydrogen bonding and hence leads to spontaneous formation of a ladder-type structure in which the arylene units tend to become coplanar. Self-assembly of the ladder structure in soln. is convincingly demonstrated by NRM- and IR-spectroscopy. The acylation of the ortho-amine functionalities with lipophilic groups leads to strong hydrogen bonding and improve soly. These large ortho-substituents do not disturb the p-delocalization of the system

U2 - 10.1021/ja9614171

DO - 10.1021/ja9614171

M3 - Article

VL - 118

SP - 8717

EP - 8718

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 36

ER -