Two-dimensional brickblock arrangement in bis-fused tetrathiafulvalene semiconductors

Takeshi Terauchi, Satoshi Sumi, Yuka Kobayashi, Yoshitaka Matsushita, Akira Sato

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)


Molecular packing arrangement is a very important factor in the charge carrier mobility of organic semiconductors, but its rational design has not been established as yet. Two-dimensional (2D) lamellar packing is an advantageous arrangement for high charge mobility, but few examples have been reported thus far. Herein we show crystal structures and the electronic properties of newly designed bis-fused tetrathiafulvalene (TTF) semiconductors with hetero substituent groups with distinct electronic effects. Unprecedented 2D lamellar alignment is achieved in a single crystal, where the bis-fused TTF rings interact three dimensionally with face-to-face and side-by-side intermolecular S···S contacts up to a total of 20 sites per π molecule and form graphitelike "brickblock" structure. The charge mobility of a single crystal is as high as 0.78 cm2 V-1s-1. Systematic investigations of the semiconductors reveal a key role of intramolecular S···O interaction between a bis-fused TTF ring and a methoxycarbonyl group in controlling efficient arrangement, leading to high mobility.

Original languageEnglish
Pages (from-to)1412-1418
Number of pages7
JournalCrystal Growth and Design
Issue number3
Publication statusPublished - 2014 Mar 5
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics


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