Well-defined oligo(pyrrole-2,5-diyl)s by the Ullmann reaction

L. Groenendaal, H.W.I. Peerlings, J.L.J. Dongen, van, E.E. Havinga, J.A.J.M. Vekemans, E.W. Meijer

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Abstract

The Ullmann coupling reaction has been used to polymerize N-t-BOC-2,5-dibromopyrrole into well-defined oligo(pyrrole-2,5-diyl)s. After optimization of the reaction conditions, i.e. using 1 wt equiv of Cu-bronze in DMF at 100 "C for 1 h, oligomers up to 25 repeating pyrrole units are obtained. Starting from 5,5‘- and 5,5"-dibrominated N-t-BOC protected bi- and terpyrrole as monomers, the polymerization is slower and a lower degree of polymerization is observed, yielding oligomers with an even lower molecular weight than those resulting from N-t-BOC-2,5-dibromopyrrole. The first 20 oligomers of poly(N-t-BOC-pyrrole)h ave been isolated by preparative HPLC. Characterization of the individual oligomers shows that they all are hydrogen terminated and possess a perfect 2,5-linkage: oligo(pyrro1e-2,5-diyl)s. The isolated oligomers have been used to study the optical and electrical properties of the oligomers as a function of chain length.
Original languageEnglish
Pages (from-to)116-123
Number of pages8
JournalMacromolecules
Volume28
Issue number1
DOIs
Publication statusPublished - 1995

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