Even and odd oligothiophene-bridged bis-naphthalimides for n-type and ambipolar organic field effect transistors

A. Riaño Carnerero, G. López Espejo, M. J. Mancheño Real, B. Eckstein, R. C. González-Cano, F. S. Melkonyan, A. Facchetti, Tobin J Marks, J. Casado, J. T. López Navarrete, J. L. Segura, R. Ponce Ortiz

Research output: Contribution to journalArticle

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Abstract

The synthesis and characterization of a new family of thiophene bridged bis-naphthalimides (2NDI-XT) are presented here. These semiconductors have been designed to have an even or an odd number of thiophene rings, with the aim of studying molecules with varying and alternant molecular dipolar moments, which are expected to significantly impact molecular packing. Following a theoretical analysis, the stability of a series of π-dimers showing either parallel or antiparallel packing dispositions has been predicted. Our results point out to a molecular packing motif in which both the NDI and oligothiophene fragments are cofacial for all the semiconductors investigated, regardless of their estimated molecular dipole moments. These, in principle, unexpected results are in good agreement with the field-effect mobilities measured in a bottom-gate top-contact transistor architecture, which show no straightforward correlation between device performance and dipolar moment. Ambipolar field-effect mobilities are recorded for the most extended π-systems, 5,5′-bis(2-hexyldecylbenzo[lmn]thieno[3′,4′:4,5]imidazo[2,1-b][3,8]phenanthroline-1,3,6(2H)-trione-10-yl)-2,2′-bithiophene, 2NDI-4T and 5,5′′-bis(2-hexyldecylbenzo[lmn]thieno[3′,4′:4,5]imidazo[2,1-b][3,8]phenanthroline-1,3,6(2H)-trione-10-yl)-2,2′:5′,2′′-terthiophene, 2NDI-5T, with the latter showing quite balanced electron and hole mobilities of 1.8 × 10-3 cm2 V-1 s-1 and 8.4 × 10-3 cm2 V-1 s-1, respectively.

Original languageEnglish
Pages (from-to)9439-9450
Number of pages12
JournalJournal of Materials Chemistry C
Volume5
Issue number36
DOIs
Publication statusPublished - Jan 1 2017

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Naphthalimides
Organic field effect transistors
Thiophenes
Phenanthrolines
Thiophene
Semiconductor materials
Hole mobility
Electron mobility
Dipole moment
Dimers
Transistors
Molecules

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

Cite this

Riaño Carnerero, A., López Espejo, G., Mancheño Real, M. J., Eckstein, B., González-Cano, R. C., Melkonyan, F. S., ... Ponce Ortiz, R. (2017). Even and odd oligothiophene-bridged bis-naphthalimides for n-type and ambipolar organic field effect transistors. Journal of Materials Chemistry C, 5(36), 9439-9450. https://doi.org/10.1039/c7tc02023f

Even and odd oligothiophene-bridged bis-naphthalimides for n-type and ambipolar organic field effect transistors. / Riaño Carnerero, A.; López Espejo, G.; Mancheño Real, M. J.; Eckstein, B.; González-Cano, R. C.; Melkonyan, F. S.; Facchetti, A.; Marks, Tobin J; Casado, J.; López Navarrete, J. T.; Segura, J. L.; Ponce Ortiz, R.

In: Journal of Materials Chemistry C, Vol. 5, No. 36, 01.01.2017, p. 9439-9450.

Research output: Contribution to journalArticle

Riaño Carnerero, A, López Espejo, G, Mancheño Real, MJ, Eckstein, B, González-Cano, RC, Melkonyan, FS, Facchetti, A, Marks, TJ, Casado, J, López Navarrete, JT, Segura, JL & Ponce Ortiz, R 2017, 'Even and odd oligothiophene-bridged bis-naphthalimides for n-type and ambipolar organic field effect transistors', Journal of Materials Chemistry C, vol. 5, no. 36, pp. 9439-9450. https://doi.org/10.1039/c7tc02023f
Riaño Carnerero A, López Espejo G, Mancheño Real MJ, Eckstein B, González-Cano RC, Melkonyan FS et al. Even and odd oligothiophene-bridged bis-naphthalimides for n-type and ambipolar organic field effect transistors. Journal of Materials Chemistry C. 2017 Jan 1;5(36):9439-9450. https://doi.org/10.1039/c7tc02023f
Riaño Carnerero, A. ; López Espejo, G. ; Mancheño Real, M. J. ; Eckstein, B. ; González-Cano, R. C. ; Melkonyan, F. S. ; Facchetti, A. ; Marks, Tobin J ; Casado, J. ; López Navarrete, J. T. ; Segura, J. L. ; Ponce Ortiz, R. / Even and odd oligothiophene-bridged bis-naphthalimides for n-type and ambipolar organic field effect transistors. In: Journal of Materials Chemistry C. 2017 ; Vol. 5, No. 36. pp. 9439-9450.
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AU - Riaño Carnerero, A.

AU - López Espejo, G.

AU - Mancheño Real, M. J.

AU - Eckstein, B.

AU - González-Cano, R. C.

AU - Melkonyan, F. S.

AU - Facchetti, A.

AU - Marks, Tobin J

AU - Casado, J.

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