Synthesis and optical properties of biphenylene ethynylene co-polymers and their model compounds

Okhil K. Nag, Kazi M. Anis-Ul-Haque, Dipen Debnath, Rockshana Begum, Muhammad Younus, Nazia Chawdhury, Gabriele Kociok-Köhn, Paul R. Raithby

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Abstract

A new series of biphenylene ethynylene co-polymers, poly(2,5-dialkoxy-4-phenyleneethynylene-4,4-biphenyleneethynylene)s of the general formula [-C ≡C-4-C6H4-C6H4-4-C ≡C-C6H2(2,5-OR)2-]n (R = C4H9 P1, C8H17 P2) has been synthesized using a palladium/copper catalyzed coupling reaction between HC ≡C-4-C6H4-C6H4-4-C ≡C-H and IC6H2(2,5-OR)2I. The new co-polymer [-C ≡C-C6H2(2,5-OC8H17)2-C ≡C-C6H2(2,5-OC4H9)2-]n P5 has also been formed where different alkoxy substituents are present on alternate arene rings in the same polymer backbone. All the polymers were characterized by IR, 1H and 13C NMR spectroscopy and by GPC. The model compounds C6H5-4-C6H4-C≡C-C6H2(2,5-OR)2-4-C6H4-C6H5 (R = C4H9 M1, C8H17 M2) have also been prepared by the reaction between C6H5-4-C6H4-C≡CH and IC6H2(2,5-OR)2I. Single crystal X-ray structures of M1, M2 and Me3Si-C≡C-4-C6H4-C6H4-4-C≡C-SiMe3 were determined with a view to obtain a better understanding of the molecular and intermolecular interactions in the solid state which has been used to explain the optical properties of the polymers derived from them. The absorption and photoluminescence spectra of the polymers, P1, P2 and P5 showed that the lowest energy band is blue shifted due to the introduction of biphenylene fragments into the alkoxy substituted poly(ethynylenephenylene)s.

Original languageEnglish
Pages (from-to)365-374
Number of pages10
JournalJournal of Chemical Sciences
Volume127
Issue number3
DOIs
Publication statusPublished - 1 Mar 2015

Keywords

  • Alkoxy substituted poly(ethynylenephenylene)
  • co-polymer
  • photoluminescence
  • sonogashira cross-coupling reaction
  • x-ray crystallography

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