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 journalArticle

47 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 - 14 Jul 2013
Externally publishedYes

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Carrier mobility
Oligomers
Luminescence
Single crystals
Field effect transistors
Hole mobility
Semiconductor materials
Excitation energy
Electron mobility
X ray crystallography
Light emission
Quantum yield
Density functional theory
Thermogravimetric analysis
furan
diphenyl
Differential scanning calorimetry
Vapors

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

Cite this

Single crystal biphenyl end-capped furan-incorporated oligomers : Influence of unusual packing structure on carrier mobility and luminescence. / Oniwa, Kazuaki; Kanagasekaran, Thangavel; Jin, Tienan; Akhtaruzzaman, Md.; Yamamoto, Yoshinori; Tamura, Hiroyuki; Hamada, Ikutaro; Shimotani, Hidekazu; Asao, Naoki; Ikeda, Susumu; Tanigaki, Katsumi.

In: Journal of Materials Chemistry C, Vol. 1, No. 26, 14.07.2013, p. 4163-4170.

Research output: Contribution to journalArticle

Oniwa, K, Kanagasekaran, T, Jin, T, Akhtaruzzaman, M, Yamamoto, Y, Tamura, H, Hamada, I, Shimotani, H, Asao, N, Ikeda, S & Tanigaki, K 2013, 'Single crystal biphenyl end-capped furan-incorporated oligomers: Influence of unusual packing structure on carrier mobility and luminescence', Journal of Materials Chemistry C, vol. 1, no. 26, pp. 4163-4170. https://doi.org/10.1039/c3tc30220b
Oniwa, Kazuaki ; Kanagasekaran, Thangavel ; Jin, Tienan ; Akhtaruzzaman, Md. ; Yamamoto, Yoshinori ; Tamura, Hiroyuki ; Hamada, Ikutaro ; Shimotani, Hidekazu ; Asao, Naoki ; Ikeda, Susumu ; Tanigaki, Katsumi. / Single crystal biphenyl end-capped furan-incorporated oligomers : Influence of unusual packing structure on carrier mobility and luminescence. In: Journal of Materials Chemistry C. 2013 ; Vol. 1, No. 26. pp. 4163-4170.
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