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

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