Side chain-directed assembly of large discotic π-conjugated molecules: Toward tuning and stabilization of mesophases

Yusuke Tsutsui, Tsuneaki Sakurai, Kenichi Kato, Masaki Takata, Shu Seki

Research output: Contribution to journalArticlepeer-review

Abstract

A representative π-conjugated motif, perylenediimide (PDI), when functionalized with taper-shaped semi-fluoroalkyl chains at one of its imide positions, self-assembled into various ordered phase structures depending on the type of side chains at the other imide position. Asymmetrical substitution by semi-fluoroalkyl/alkyl chains allowed the PDI molecule to form a rectangular columnar liquid crystalline mesophase while semi-fluoroalkyl/triethyleneglycol-substitution resulted in a lamellar-packed crystalline mesophase. In both mesophases, the immiscible nature of superhydrophobic/hydrophobic or superhydrophobic/hydrophilic segments works as the major droving force to lead semi-fluoroalkyl/alkyl or semi-fluoroalkyl/oxyethyleneglycol nano-domains, resulting in high stability of the mesophases with the wide temperature range over 100ºC. The compound decorated with tapered semi-fluoroalkyl chains at the both imide positions exhibited complicated crystalline ordered phases with high thermal stability.

Original languageEnglish
Pages (from-to)749-753
Number of pages5
JournalJournal of Photopolymer Science and Technology
Volume28
Issue number6
DOIs
Publication statusPublished - 2015 Nov 16
Externally publishedYes

Keywords

  • Columnar phase
  • Immiscible chains
  • Liquid crystal
  • Perylenediimide

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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