High-quality conjugated polymers via one-pot Suzuki-Miyaura homopolymerization

Difei Zhou, Nutifafa Y. Doumon, Mustapha Abdu-Aguye, Davide Bartesaghi, Maria A. Loi, L. Jan Anton Koster, Ryan C. Chiechi, Jan C. Hummelen

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

This paper describes a one-pot Suzuki-Miyaura homopolymerization that involves in situ borylation/cross coupling of dibrominated donor-acceptor conjugated macromonomers, in contrast to the standard Stille copolymerization of thienosilole and isoindigo monomers. Reaction kinetics investigation reveals that bis(pinacolato)diboron promotes an efficient polymerization. The homopolymer showed blue-shifted absorption compared to the Stille copolymer, which is rationalized by quantum chemical calculations of a series of oligomers containing various donor-acceptor configurations. The calculations suggest that the homopolymerization of asymmetrical macromonomers likely introduced both acceptor-acceptor and donor-donor segments into the backbone. The acceptor-acceptor segment is found to contribute mostly to the blue-shift of maximum absorption wavelength. Furthermore, detailed analysis of MALDI-TOF (matrix-assisted laser-desorption ionization-time of flight) spectra of these two polymers indicated that while the homopolymer is well defined, the Stille copolymer is end-capped mostly with the thienosilole moieties and/or methyl groups, implicating that destannylation and methyl transfer are the most-likely chain-termination pathways that limit high molecular weight. This is in sharp contrast to the homopolymerization, where chain-terminators are required to control the molecular weight for obtaining soluble material. The photovoltaic performances of bulk-heterojunction solar cells based on these polymers are compared.

Original languageEnglish (US)
Pages (from-to)27762-27769
Number of pages8
JournalRSC Advances
Volume7
Issue number44
DOIs
StatePublished - 2017

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • General Chemical Engineering

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