Single crystal biphenyl end-capped furan-incorporated oligomers: Influence of unusual packing structure on carrier mobility and luminescence

Kazuaki Oniwa, Thangavel Kanagasekaran, Tienan Jin, Md Akhtaruzzaman, Yoshinori Yamamoto, Hiroyuki Tamura, Ikutaro Hamada, Hidekazu Shimotani, Naoki Asao, Susumu Ikeda, Katsumi Tanigaki

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

Abstract

We report the synthesis and characterization of two new furan-based biphenyl end-capped oligomers, 2-([1,1′-biphenyl]-4-yl)-5-(5-([1,1′- biphenyl]-4-yl)thiophen-2-yl)furan (BPFT) and 5,5′-di([1,1′- biphenyl]-4-yl)-2,2′-bifuran (BP2F) as candidate semiconductors for organic light-emitting field effect transistors (OLETs). Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) showed the high thermostability of these furan-based semiconductors. X-Ray crystallography of single crystals grown by physical vapor transfer (PVT) method revealed a complicated herringbone packing of BPFT stacking with unusual flat and bent structures, which is different from that of BP2F and the bithiophene-based analogue 5,5′-di([1,1′-biphenyl]-4-yl)-2,2′-bithiophene (BP2T). BPFT single crystal showed a higher absolute quantum yield (51%) compared to that of BP2F and BP2T. Density Functional Theory (DFT) calculations showed that the different excitation energies between flat and bent structures led to the asymmetric transition dipoles in dark state of BPFT H-aggregates, which explains the highest PLQY of BPFT single crystal. Single crystal FET based on BPFT showed an ambipolar characteristic with high hole and electron mobilities, while single crystal FET based on BP2F exhibited p-type characteristic with a high hole mobility. Light emission was observed from the single-crystal FET based on BPFT.

Original languageEnglish
Pages (from-to)4163-4170
Number of pages8
JournalJournal of Materials Chemistry C
Volume1
Issue number26
DOIs
Publication statusPublished - 2013 Jul 14

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

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