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

Research output: Contribution to journalArticleAcademicpeer-review

85 Citations (Scopus)
67 Downloads (Pure)

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 languageEnglish
Pages (from-to)8717-8718
JournalJournal of the American Chemical Society
Volume118
Issue number36
DOIs
Publication statusPublished - 1996

Fingerprint

Ladders
Hydrogen Bonding
Oligomers
Hydrogen
Hydrogen bonds
Polymers
Pyrazines
Diamines
Acylation
Amines
Spectrum Analysis
Self assembly
Infrared spectroscopy

Cite this

@article{8bb0484b04754945923a273dc5ae9cb4,
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",
volume = "118",
pages = "8717--8718",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "36",

}

pi-Conjugated oligomers and polymers with a self-assembled ladder-like structure. / Delnoye, D.A.P.; Sijbesma, R.P.; Vekemans, J.A.J.M.; Meijer, E.W.

In: Journal of the American Chemical Society, Vol. 118, No. 36, 1996, p. 8717-8718.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

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 -