Synthesis of novel dithienothiophene- and 2,7-carbazole-based conjugated polymers and H-bonded effects on electrochromic and photovoltaic properties

Hsiao Ping Fang, Jia Wei Lin, I. Hung Chiang, Chih Wei Chu*, Kung-Hwa Wei, Hong-Cheu Lin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Three kinds of dithienothiophene/carbazole-based conjugated polymers (P1-P3), which bear acid-protected and benzoic acid pendants in P2 and P3, respectively, were synthesized via Suzuki coupling reaction. Interestingly, P1-P3 exhibited reversible electrochromism during the oxidation processes of cyclic voltammogram studies, and P3 (with H-bonds) revealed the best electrochromic property with the most noticeable color change. According to powder X-ray diffraction (XRD) analysis, these polymers exhibited obvious diffraction features indicating bilayered packings between polymer backbones and π-π stacking between layers in the solid state. Compared with the XRD data of P2 (without H-bands), H-bonds of P3 induced a higher crystallinity in the small-angle region (corresponding to a higher ordered bilayered packings between polymer backbones), but with a similar crystallinity in the wide angle region indicating a comparable π-π stacking distance between layers. Moreover, based on the preliminary photovoltaic properties of PSC devices (P1-P3 blended individually with PCBM acceptor in the weight ratio of 1:1), P3 (with H-bonds) possessed the highest power conversion efficiency of 0.61% (with J sc = 2.26 mA/cm 2, FF = 29.8%, and V oc = 0.9 V). In contrast to P2 (without H-bands), the thermal stability, crystallinity, and electrochromic along with photovoltaic properties of P3 were generally enhanced due to its H-bonded effects.

Original languageEnglish
Pages (from-to)5011-5022
Number of pages12
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume50
Issue number24
DOIs
StatePublished - 15 Dec 2012

Keywords

  • electrochromism
  • functionalization of polymers
  • heterocyclic conjugated polymer
  • solar cell
  • supramolecular structures
  • WAXS

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