New semiconductors based on 2,2′-ethyne-1,2-diylbis[3-(alk-1-yn-1-yl) thiophene] for organic opto-electronics

Pierre Luc T Boudreault, Jonathan W. Hennek, Stephen Loser, Rocio Ponce Ortiz, Brian J. Eckstein, Antonio Facchetti, Tobin J Marks

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

We report the synthesis and properties of three novel acetylenic materials based on the new electron-rich building block, 2,2′-ethyne-1,2-diylbis[3- (alk-1-yn-1-yl)thiophene] (EBT). The synthesis of this new nonacene core is efficient and straightforward, and variation among n-hexyl, n-tetradecyl, and 2-ethylhexyl substituents substantially impacts the materials properties. Appending 2-ethylhexyl substituted diketopyrrolopyrrole (DPP) units to either terminus of the EBT core yields a series of low band gap molecules that are characterized in detail by a range of experimental microstructure and electronic structure probes and by density functional theory (DFT) computation. Detailed morphology/microstructure characterization of spin-cast films by X-ray diffraction and AFM reveals instructive microstructure and electronic/ photovoltaic response relationships in both organic field-effect transistors and bulk-heterojunction organic photovoltaic cells. Thus, the former devices exhibit hole mobilities (μ h) as large as ∼0.2 cm 2/(V s) which fall as thermal annealing increases long-range order. The latter devices using PC 61BM as the electron acceptor exhibit power conversion efficiencies as high as ∼2%, which appear to fall as the materials become less ordered. These results are in accord with a model where evolving grain boundaries and crystallinity impedes hole transport and excitonic charge generation.

Original languageEnglish
Pages (from-to)2929-2942
Number of pages14
JournalChemistry of Materials
Volume24
Issue number15
DOIs
Publication statusPublished - Aug 14 2012

Fingerprint

Thiophenes
Acetylene
Thiophene
Electronic equipment
Semiconductor materials
Microstructure
Organic field effect transistors
Hole mobility
Electrons
Photovoltaic cells
Conversion efficiency
Electronic structure
Density functional theory
Heterojunctions
Materials properties
Grain boundaries
Energy gap
Annealing
X ray diffraction
Molecules

Keywords

  • arylacetylene
  • EBT
  • OPVs
  • OTFTs
  • small molecules

ASJC Scopus subject areas

  • Materials Chemistry
  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Boudreault, P. L. T., Hennek, J. W., Loser, S., Ortiz, R. P., Eckstein, B. J., Facchetti, A., & Marks, T. J. (2012). New semiconductors based on 2,2′-ethyne-1,2-diylbis[3-(alk-1-yn-1-yl) thiophene] for organic opto-electronics. Chemistry of Materials, 24(15), 2929-2942. https://doi.org/10.1021/cm301095x

New semiconductors based on 2,2′-ethyne-1,2-diylbis[3-(alk-1-yn-1-yl) thiophene] for organic opto-electronics. / Boudreault, Pierre Luc T; Hennek, Jonathan W.; Loser, Stephen; Ortiz, Rocio Ponce; Eckstein, Brian J.; Facchetti, Antonio; Marks, Tobin J.

In: Chemistry of Materials, Vol. 24, No. 15, 14.08.2012, p. 2929-2942.

Research output: Contribution to journalArticle

Boudreault, PLT, Hennek, JW, Loser, S, Ortiz, RP, Eckstein, BJ, Facchetti, A & Marks, TJ 2012, 'New semiconductors based on 2,2′-ethyne-1,2-diylbis[3-(alk-1-yn-1-yl) thiophene] for organic opto-electronics', Chemistry of Materials, vol. 24, no. 15, pp. 2929-2942. https://doi.org/10.1021/cm301095x
Boudreault PLT, Hennek JW, Loser S, Ortiz RP, Eckstein BJ, Facchetti A et al. New semiconductors based on 2,2′-ethyne-1,2-diylbis[3-(alk-1-yn-1-yl) thiophene] for organic opto-electronics. Chemistry of Materials. 2012 Aug 14;24(15):2929-2942. https://doi.org/10.1021/cm301095x
Boudreault, Pierre Luc T ; Hennek, Jonathan W. ; Loser, Stephen ; Ortiz, Rocio Ponce ; Eckstein, Brian J. ; Facchetti, Antonio ; Marks, Tobin J. / New semiconductors based on 2,2′-ethyne-1,2-diylbis[3-(alk-1-yn-1-yl) thiophene] for organic opto-electronics. In: Chemistry of Materials. 2012 ; Vol. 24, No. 15. pp. 2929-2942.
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