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Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers†
Frank Brouwer,Jan Alma,Hennie Valkenier,Thomas P. Voortman,Jorrit Hillebrand,Ryan C. Chiechi,Jan C. Hummelen
Journal of Materials Chemistry Pub Date : 11/17/2010 00:00:00 , DOI:10.1039/C0JM02359K
Abstract

We demonstrate the use of bis(pinacolato)diboron to directly polymerize symmetric, bisbromo, thiophene-based monomers via a Suzuki homo-polymerization to form co-polymers in less steps than the corresponding co-polymerization. We compare this method to the commonly used Stille co-polymerization by preparing four thiophene-based co-polymers using both methods. We use MALDI-TOF mass spectrometry to show that this new method produces high-quality, uniform polymers with narrow distributions of end-groups. By varying the electronegativity of the monomers, we demonstrate rudimentary control over these end-groups, forming either bis-H-, mono-H-mono-Br-, or bis-Br-terminated polymers in order of increasing electronegativity.

Graphical abstract: Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers
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