Two-dimensional extended π-conjugated anthracene-based molecules bearing 4-ethynyl-7-(5-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole at 2,6- and 9,10-substitution positions

Jung A. Hur, Sun Jae Kim, Kyung Hwan Kim, Tae Wan Lee, Kihyun Kim, Jicheol Shin, Kyung Seok Hwang, Byung Doo Chin, Dong Hoon Choi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

New 4-ethynyl-7-(5-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole-containing conjugated molecules were synthesized via the Sonogashira coupling reaction. The synthesized anthracene-based molecules showed good solubility in common organic solvents and had good self-film-forming properties. The semiconducting properties of the two synthesized π-conjugated molecules, 4 and 8, were evaluated by using the molecules in organic thin-film transistors (OTFTs). As-spun films of these molecules showed fairly high charge carrier mobilities, 0.010-0.10 cm 2 V -1 s -1 (I ON/I OFF > 10 3). The high charge carrier mobilities were attributed to the strong intermolecular interaction, which resulted in easy crystallization and dense coverage of the insulator surface. In addition, the two molecules were used to fabricate organic photovoltaic (OPV) cells with methanofullerene [6,6]-phenyl C 61-butyric acid methyl ester (PC 61BM), without thermal annealing. The best preliminary results were obtained for the photovoltaic cell containing 8; the open-circuit voltage, short-circuit current density, and fill factor were 0.76 V, 1.65 mA cm -2, and 0.44, respectively, and the overall power conversion efficiency (PCE) was 0.55%.

Original languageEnglish
Pages (from-to)2776-2784
Number of pages9
JournalSynthetic Metals
Volume161
Issue number23-24
DOIs
Publication statusPublished - 2012 Jan 1

Fingerprint

Bearings (structural)
Thiadiazoles
Anthracene
anthracene
Substitution reactions
substitutes
Molecules
molecules
Photovoltaic cells
photovoltaic cells
Carrier mobility
carrier mobility
Charge carriers
charge carriers
Butyric acid
Butyric Acid
butyric acid
Open circuit voltage
Thin film transistors
short circuit currents

Keywords

  • Anthracene
  • Bulk heterojunction
  • Conjugated molecules
  • Mobility
  • Organic thin film transistor
  • Photovoltaic cell
  • Semiconductor

ASJC Scopus subject areas

  • Mechanical Engineering
  • Mechanics of Materials
  • Materials Chemistry
  • Metals and Alloys
  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics

Cite this

Two-dimensional extended π-conjugated anthracene-based molecules bearing 4-ethynyl-7-(5-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole at 2,6- and 9,10-substitution positions. / Hur, Jung A.; Kim, Sun Jae; Kim, Kyung Hwan; Lee, Tae Wan; Kim, Kihyun; Shin, Jicheol; Hwang, Kyung Seok; Chin, Byung Doo; Choi, Dong Hoon.

In: Synthetic Metals, Vol. 161, No. 23-24, 01.01.2012, p. 2776-2784.

Research output: Contribution to journalArticle

Hur, Jung A. ; Kim, Sun Jae ; Kim, Kyung Hwan ; Lee, Tae Wan ; Kim, Kihyun ; Shin, Jicheol ; Hwang, Kyung Seok ; Chin, Byung Doo ; Choi, Dong Hoon. / Two-dimensional extended π-conjugated anthracene-based molecules bearing 4-ethynyl-7-(5-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole at 2,6- and 9,10-substitution positions. In: Synthetic Metals. 2012 ; Vol. 161, No. 23-24. pp. 2776-2784.
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AU - Kim, Kyung Hwan

AU - Lee, Tae Wan

AU - Kim, Kihyun

AU - Shin, Jicheol

AU - Hwang, Kyung Seok

AU - Chin, Byung Doo

AU - Choi, Dong Hoon

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AB - New 4-ethynyl-7-(5-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole-containing conjugated molecules were synthesized via the Sonogashira coupling reaction. The synthesized anthracene-based molecules showed good solubility in common organic solvents and had good self-film-forming properties. The semiconducting properties of the two synthesized π-conjugated molecules, 4 and 8, were evaluated by using the molecules in organic thin-film transistors (OTFTs). As-spun films of these molecules showed fairly high charge carrier mobilities, 0.010-0.10 cm 2 V -1 s -1 (I ON/I OFF > 10 3). The high charge carrier mobilities were attributed to the strong intermolecular interaction, which resulted in easy crystallization and dense coverage of the insulator surface. In addition, the two molecules were used to fabricate organic photovoltaic (OPV) cells with methanofullerene [6,6]-phenyl C 61-butyric acid methyl ester (PC 61BM), without thermal annealing. The best preliminary results were obtained for the photovoltaic cell containing 8; the open-circuit voltage, short-circuit current density, and fill factor were 0.76 V, 1.65 mA cm -2, and 0.44, respectively, and the overall power conversion efficiency (PCE) was 0.55%.

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