Contrasting effect of alkylation on the ordering structure in isomeric naphthodithiophene-based polymers

Itaru Osaka, Yoshinobu Houchin, Masayuki Yamashita, Takeshi Kakara, Noriko Takemura, Tomoyuki Koganezawa, Kazuo Takimiya

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Semiconducting polymers with alkylated naphtho[1,2-b:5,6-b′] dithiophene (NDT3) and naphtho[2,1-b:6,5-b′]dithiophene (NDT4) are synthesized and characterized. The solubility of the present polymers is significantly improved as compared to the nonalkylated counterparts with preserving the good charge transport properties. Interestingly, the effect of alkylation is found to be quite distinct between the NDT3 and NDT4 cores. In the NDT3-based polymers, alkylation leads to the more ordered backbone structure and thus the increased crystalline order in the thin film. On the other hand, in the NDT4-based polymers, alkylation is detriment to the backbone ordering, which gives rise to the face-on orientation or amorphous like film structure. This difference can be qualitatively explained by the different alkyl placement; all the neighboring alkyl groups are in the anti arrangement in the NDT3-based polymers, whereas the arrangement is a mixture of anti and syn in the NDT4-based polymers, which likely causes steric impact on the backbone. These observations make us better understood how the alkylation affect the ordering structures, which would be an important guideline for the design of superior semiconducting polymers.

Original languageEnglish
Pages (from-to)3502-3510
Number of pages9
JournalMacromolecules
Volume47
Issue number10
DOIs
Publication statusPublished - 2014 May 27
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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