Regioisomeric Polythiophene Derivatives: Synthesis and Structure-Property Relationships for Organic Electronic Devices

Young Woong Lee, Kawon Pak, Song Yi Park, Na Gyeong An, Junghoon Lee, Jin Young Kim, Han Young Woo

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Three types of tail-to-tail (PDCBTTT), head-to-tail (PDCBTHT), and head-to-head (PDCBTHH) regioisomeric polythiophene copolymers were synthesized by modification of the substitution positions of their alkoxycarbonyl side-chains. Chain conformation, and optical, electrochemical, morphological, and charge-transport characteristics of the polymers were significantly influenced by their regiochemistry. PDCBTHH showed an amorphous morphology due to strong steric hindrance between its head-to-head alkoxycarbonyl side-chains, resulting in the poorest performance in organic solar cells and transistors among three types. PDCBTHT had a regiorandom structure with both head-to-tail and tail-to-head linkages in a polymer chain. As determined by field-effect mobility measurements, a highly regioregular and planar PDCBTTT exhibited the highest hole mobility (μ = 0.065 cm2 V-1s-1), which was two orders of magnitude higher than that of the regiorandom PDCBTHT. The highest photovoltaic performance was also measured for PDCBTTT:a fullerene acceptor (PC71BM), by maintaining the packed structures of pristine PDCBTTT polymers in the blend with PC71BM. Altering the topology of alkoxycarbonyl side-chains of the copolymers resulted in significant differences in crystalline morphologies and electrical properties and thus should be carefully considered in the molecular design of organic semiconductors. [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)772-781
Number of pages10
JournalMacromolecular Research
Volume28
Issue number8
DOIs
Publication statusPublished - 2020 Jul 1

Keywords

  • film morphology
  • organic field effect transistors
  • organic photovoltaics
  • regioisomer

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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