Synthesis and Properties of New N-Heteroheptacenes for Solution-Based Organic Field Effect Transistors

Fei Zhou, Sheng Liu, Bernard D. Santarsiero, Donald J. Wink, Damien Boudinet, Antonio Facchetti, Tom Driver*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


A series of N-heteroheptacenes was synthesized from ortho-thiophene-substituted aryl azides using a Rh2II-catalyzed C−H bond amination reaction to construct the thienoindole moieties. This reaction tolerated the presence of electron-donating or withdrawing groups on the aryl azide without adversely affecting the yield of the amination reaction. The central thiophene ring was created from two thienoindole pieces through a Pd-catalyzed Stille reaction to install the thioether followed by a Cu-mediated Ullman reaction to trigger the cyclization. The photophysical and electrochemical properties of the resulting focused library of N-heteroheptacenes revealed that the electronic nature is controlled by the arene substituent while single crystals grown reveal that the packing motif is influenced by the N-substituent. Solution-processed thin-film OFET devices were fabricated with the N-heteroheptacenes, and one exhibited a hole-mobility of 0.02 cm2 V−1 s−1.

Original languageEnglish (US)
Pages (from-to)12542-12549
Number of pages8
JournalChemistry - A European Journal
Issue number51
StatePublished - Sep 12 2017


  • C−H bond amination
  • N-heteroacenes
  • field effect transistor
  • nitrenes
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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