The effect of single atom replacement on organic thin film transistors: Case of thieno[3,2-b] pyrrole vs. furo[3,2-b] pyrrole

Chandima Bulumulla, Ruwan Gunawardhana, Sang Ha Yoo, Cody R. Mills, Ruvanthi N. Kularatne, Thomas N. Jackson, Michael C. Biewer, Enrique D. Gomez, Mihaela C. Stefan

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Despite polypyrrole having higher conductivities compared to polythiophenes, pyrrole based materials have garnered less attention in the organic electronics community due to their instability in air. Construction of stable pyrrolic units could be achieved by fusing relatively unstable pyrrole with stable aromatic rings. In this report, we discuss and compare the organic field-effect transistor performances of the smallest S,N-heteroacene and O,N-heteroacene, thieno[3,2-b]pyrrole and furo[3,2-b]pyrrole, respectively, in donor-acceptor-donor type organic semiconducting small molecules. Since both building blocks are highly electron-rich, thiophene flanked 5,6-difluorobenzo[c][1,2,5]thiadiazole is employed as a central electron-withdrawing unit. The small molecule containing thieno[3,2-b]pyrrole exhibit moderate hole mobilities (10-3 cm2 V-1 s-1) irrespective of the annealing temperature. In contrast, the small molecule bearing furo[3,2-b]pyrrole is completely inactive in field-effect transistors. To the best of our knowledge this is the first report to compare the smallest units of S,N and O,N-heteroacenes for organic field-effect transistors.

Original languageEnglish (US)
Pages (from-to)10050-10058
Number of pages9
JournalJournal of Materials Chemistry C
Volume6
Issue number37
DOIs
StatePublished - Jan 1 2018

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Pyrroles
Thin film transistors
Organic field effect transistors
Atoms
Molecules
Bearings (structural)
Hole mobility
Electrons
Polypyrroles
Thiophene
Field effect transistors
Electronic equipment
Thiadiazoles
Annealing
Thiophenes
Polymers
Air
Temperature

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Chemistry

Cite this

Bulumulla, Chandima ; Gunawardhana, Ruwan ; Yoo, Sang Ha ; Mills, Cody R. ; Kularatne, Ruvanthi N. ; Jackson, Thomas N. ; Biewer, Michael C. ; Gomez, Enrique D. ; Stefan, Mihaela C. / The effect of single atom replacement on organic thin film transistors : Case of thieno[3,2-b] pyrrole vs. furo[3,2-b] pyrrole. In: Journal of Materials Chemistry C. 2018 ; Vol. 6, No. 37. pp. 10050-10058.
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abstract = "Despite polypyrrole having higher conductivities compared to polythiophenes, pyrrole based materials have garnered less attention in the organic electronics community due to their instability in air. Construction of stable pyrrolic units could be achieved by fusing relatively unstable pyrrole with stable aromatic rings. In this report, we discuss and compare the organic field-effect transistor performances of the smallest S,N-heteroacene and O,N-heteroacene, thieno[3,2-b]pyrrole and furo[3,2-b]pyrrole, respectively, in donor-acceptor-donor type organic semiconducting small molecules. Since both building blocks are highly electron-rich, thiophene flanked 5,6-difluorobenzo[c][1,2,5]thiadiazole is employed as a central electron-withdrawing unit. The small molecule containing thieno[3,2-b]pyrrole exhibit moderate hole mobilities (10-3 cm2 V-1 s-1) irrespective of the annealing temperature. In contrast, the small molecule bearing furo[3,2-b]pyrrole is completely inactive in field-effect transistors. To the best of our knowledge this is the first report to compare the smallest units of S,N and O,N-heteroacenes for organic field-effect transistors.",
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The effect of single atom replacement on organic thin film transistors : Case of thieno[3,2-b] pyrrole vs. furo[3,2-b] pyrrole. / Bulumulla, Chandima; Gunawardhana, Ruwan; Yoo, Sang Ha; Mills, Cody R.; Kularatne, Ruvanthi N.; Jackson, Thomas N.; Biewer, Michael C.; Gomez, Enrique D.; Stefan, Mihaela C.

In: Journal of Materials Chemistry C, Vol. 6, No. 37, 01.01.2018, p. 10050-10058.

Research output: Contribution to journalArticle

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T1 - The effect of single atom replacement on organic thin film transistors

T2 - Case of thieno[3,2-b] pyrrole vs. furo[3,2-b] pyrrole

AU - Bulumulla, Chandima

AU - Gunawardhana, Ruwan

AU - Yoo, Sang Ha

AU - Mills, Cody R.

AU - Kularatne, Ruvanthi N.

AU - Jackson, Thomas N.

AU - Biewer, Michael C.

AU - Gomez, Enrique D.

AU - Stefan, Mihaela C.

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Y1 - 2018/1/1

N2 - Despite polypyrrole having higher conductivities compared to polythiophenes, pyrrole based materials have garnered less attention in the organic electronics community due to their instability in air. Construction of stable pyrrolic units could be achieved by fusing relatively unstable pyrrole with stable aromatic rings. In this report, we discuss and compare the organic field-effect transistor performances of the smallest S,N-heteroacene and O,N-heteroacene, thieno[3,2-b]pyrrole and furo[3,2-b]pyrrole, respectively, in donor-acceptor-donor type organic semiconducting small molecules. Since both building blocks are highly electron-rich, thiophene flanked 5,6-difluorobenzo[c][1,2,5]thiadiazole is employed as a central electron-withdrawing unit. The small molecule containing thieno[3,2-b]pyrrole exhibit moderate hole mobilities (10-3 cm2 V-1 s-1) irrespective of the annealing temperature. In contrast, the small molecule bearing furo[3,2-b]pyrrole is completely inactive in field-effect transistors. To the best of our knowledge this is the first report to compare the smallest units of S,N and O,N-heteroacenes for organic field-effect transistors.

AB - Despite polypyrrole having higher conductivities compared to polythiophenes, pyrrole based materials have garnered less attention in the organic electronics community due to their instability in air. Construction of stable pyrrolic units could be achieved by fusing relatively unstable pyrrole with stable aromatic rings. In this report, we discuss and compare the organic field-effect transistor performances of the smallest S,N-heteroacene and O,N-heteroacene, thieno[3,2-b]pyrrole and furo[3,2-b]pyrrole, respectively, in donor-acceptor-donor type organic semiconducting small molecules. Since both building blocks are highly electron-rich, thiophene flanked 5,6-difluorobenzo[c][1,2,5]thiadiazole is employed as a central electron-withdrawing unit. The small molecule containing thieno[3,2-b]pyrrole exhibit moderate hole mobilities (10-3 cm2 V-1 s-1) irrespective of the annealing temperature. In contrast, the small molecule bearing furo[3,2-b]pyrrole is completely inactive in field-effect transistors. To the best of our knowledge this is the first report to compare the smallest units of S,N and O,N-heteroacenes for organic field-effect transistors.

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