Rational design of ambipolar organic semiconductors: Is core planarity central to ambipolarity in thiophene-naphthalene semiconductors?

Rocío Ponce Ortiz, Helena Herrera, Carlos Seoane, José L. Segura, Antonio Facchetti, Tobin J Marks

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Herein, we report a new family of naphthaleneamidinemonoimide-fused oligothiophene semiconductors designed for facile charge transport in organic field-effect transistors (OFETs). These molecules have planar skeletons that induce high degrees of crystallinity and hence good charge-transport properties. By modulating the length of the oligothiophene fragment, the majority carrier charge transport can be switched from n-type to ambipolar behavior. The highest FET performance is achieved for solution-processed films of 10-[(2,2′- bithiophen)-5-yl]-2-octylbenzo[lmn]thieno[3′,4′:4,5]imidazo[2,1-b] [3,8]phenanthroline-1,3,6(2 H)-trione (NDI-3 Tp), with optimized film mobilities of 2à- 10 -2 and 0.7à- 10 -2 cm 2 V -1 s -1 for electrons and holes, respectively. Finally, these planar semiconductors are compared with their twisted-skeleton counterparts, which exhibit only n-type mobility, in order to understand the origin of the ambipolarity in this new series of molecular semiconductors.

Original languageEnglish
Pages (from-to)532-543
Number of pages12
JournalChemistry - A European Journal
Volume18
Issue number2
DOIs
Publication statusPublished - Jan 9 2012

Fingerprint

Thiophenes
Semiconducting organic compounds
Thiophene
Naphthalene
Charge transfer
Semiconductor materials
Organic field effect transistors
Phenanthrolines
Field effect transistors
Transport properties
Molecules
Electrons
naphthalene

Keywords

  • ambipolarity
  • naphthalenes
  • organic field-effect transistors
  • semiconductors
  • sulfur heterocycles

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Rational design of ambipolar organic semiconductors : Is core planarity central to ambipolarity in thiophene-naphthalene semiconductors? / Ortiz, Rocío Ponce; Herrera, Helena; Seoane, Carlos; Segura, José L.; Facchetti, Antonio; Marks, Tobin J.

In: Chemistry - A European Journal, Vol. 18, No. 2, 09.01.2012, p. 532-543.

Research output: Contribution to journalArticle

Ortiz, Rocío Ponce ; Herrera, Helena ; Seoane, Carlos ; Segura, José L. ; Facchetti, Antonio ; Marks, Tobin J. / Rational design of ambipolar organic semiconductors : Is core planarity central to ambipolarity in thiophene-naphthalene semiconductors?. In: Chemistry - A European Journal. 2012 ; Vol. 18, No. 2. pp. 532-543.
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