Organic n-channel field-effect transistors based on arylenediimide- thiophene derivatives

Rocío Ponce Ortiz, Helena Herrera, Raúl Blanco, Hui Huang, Antonio Facchetti, Tobin J Marks, Yan Zheng, José L. Segura

Research output: Contribution to journalArticle

109 Citations (Scopus)

Abstract

The synthesis, structural, electrochemical, and thin film electrical and electronic structural properties of a series of arylene diimide-oligothiophene n-type semiconductors are reported. This family of compounds allows analysis of the effects on thin film transistor performance of the following: (i) oligothiophene backbone catenation; (ii) naphthalenediimide vs perylenediimide core interchange; (iii) phenylene group introduction in the oligothiophene backbone. Electrochemical experiments indicate similar redox energetics for all members of this series, while thin film transistor measurements reveal markedly different charge transport performances. The highest electron mobility of 0.35 cm2 V-1 s-1 is recorded for films of benzo[lmn]thieno[3′,4′:4,5]imidazo[2,1-b][3,8]phenanthroline-1,3, 6(2H)-trione, 2-octyl (NDI-1T). Solution-processed field effect transistors were also fabricated and surprisingly exhibit electrical performances surpassing that of the vapor-deposited films in the case of isoquino[6′,5′, 4′:10,5,6]anthra[2,1,9-def]thieno[3′,4′:4,5]imidazo[2,1-a] isoquinoline-1,3,8(2H)-trione, 2-(1-heptyloctyl)-10,12-di-2-thienyl (PDI-3T).

Original languageEnglish
Pages (from-to)8440-8452
Number of pages13
JournalJournal of the American Chemical Society
Volume132
Issue number24
DOIs
Publication statusPublished - Jun 23 2010

Fingerprint

Thiophenes
Semiconductors
Phenanthrolines
Thiophene
Thin film transistors
Field effect transistors
Oxidation-Reduction
Electrons
Derivatives
Electron mobility
Interchanges
Charge transfer
Structural properties
Vapors
Semiconductor materials
Thin films
Experiments
naphthalenediimide
perylenediimide
heparinized hydrophilic polymer

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Organic n-channel field-effect transistors based on arylenediimide- thiophene derivatives. / Ortiz, Rocío Ponce; Herrera, Helena; Blanco, Raúl; Huang, Hui; Facchetti, Antonio; Marks, Tobin J; Zheng, Yan; Segura, José L.

In: Journal of the American Chemical Society, Vol. 132, No. 24, 23.06.2010, p. 8440-8452.

Research output: Contribution to journalArticle

Ortiz, RP, Herrera, H, Blanco, R, Huang, H, Facchetti, A, Marks, TJ, Zheng, Y & Segura, JL 2010, 'Organic n-channel field-effect transistors based on arylenediimide- thiophene derivatives', Journal of the American Chemical Society, vol. 132, no. 24, pp. 8440-8452. https://doi.org/10.1021/ja1018783
Ortiz, Rocío Ponce ; Herrera, Helena ; Blanco, Raúl ; Huang, Hui ; Facchetti, Antonio ; Marks, Tobin J ; Zheng, Yan ; Segura, José L. / Organic n-channel field-effect transistors based on arylenediimide- thiophene derivatives. In: Journal of the American Chemical Society. 2010 ; Vol. 132, No. 24. pp. 8440-8452.
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