Toward ultralow-bandgap liquid crystalline semiconductors: Use of triply fused metalloporphyrin trimer-pentamer as extra-large π-extended mesogenic motifs

Seiya Tanaka, Tsuneaki Sakurai, Yoshihito Honsho, Akinori Saeki, Shu Seki, Kenichi Kato, Masaki Takata, Atsuhiro Osuka, Takuzo Aida

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

In contrast with their dimeric homologue, triply fused zinc porphyrin trimer-pentamer, as extra-large π-extended mesogens, assemble into columnar liquid crystals (LCs) when combined with 3,4,5-tri(dodecyloxy)phenyl side groups (3 P Zn-5 P Zn, Figure 1). Their LC mesophases develop over a wide temperature range, namely, 41-280 °C (on heating) for 5 P Zn, and all adopt an oblique columnar geometry, typically seen in columnar LC materials involving strong mesogenic interactions. These LC materials are characterized by their wide light-absorption windows from the entire visible region up to a near infrared (NIR) region. Such ultralow-bandgap LC materials are chemically stable and serve as hole transporters, in which 5 P Zn gives the largest charge carrier mobility (2.4×10 -2 cm V -1 s -1) among the series. Despite a big dimensional difference, they coassemble without phase separation, in which the resultant LC materials display essentially no deterioration of the intrinsic conducting properties. Low bandgap: Triply fused zinc porphyrin trimer-pentamers serve as extra-large π-extended mesogens for the formation of ultralow bandgap columnar liquid-crystalline (LC) semiconductors with very wide LC mesophase temperature ranges and light-absorption windows (see figure). The mobility of pentramer is roughly one order of magnitude greater than that of dimeric reference.

Original languageEnglish
Pages (from-to)10554-10561
Number of pages8
JournalChemistry - A European Journal
Volume18
Issue number34
DOIs
Publication statusPublished - 2012 Aug 20
Externally publishedYes

Keywords

  • liquid crystals
  • organic electronics
  • porphyrins
  • self-assembly
  • semiconductors

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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