Isomeric carbazolocarbazoles: Synthesis, characterization and comparative study in Organic Field Effect Transistors

Miriam Más-Montoya, Rocío Ponce Ortiz, David Curiel, Arturo Espinosa, Magali Allain, Antonio Facchetti, Tobin J. Marks

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

We report here the synthesis and characterization of a new family of isomeric carbazolocarbazole derivatives, namely carbazolo[1,2-a]carbazole, carbazolo[3,2-b]carbazole and carbazolo[4,3-c]carbazole. Thermal, optical, electrochemical, morphological and semiconducting properties have been studied to understand the influence of geometrical isomerism on the optoelectronic properties of these compounds. Different packing patterns have been observed by single crystal X-ray diffraction (XRD) which then correlate with the different morphologies of the evaporated thin films studied by XRD and Atomic Force Microscopy (AFM). The effect of N-substituents has also been evaluated for one of the isomers revealing a noticeable influence on the performance as organic semiconductors in Organic Field Effect Transistors (OFETs). A good p-channel field effect has been determined for N,N′-dioctylcarbazolo[4,3-c]carbazole with a mobility of 0.02 cm2 V-1 s-1 and I on/Ioff ratio of 106 in air. These preliminary results demonstrate the promising properties of molecular carbazolocarbazole systems which should be further explored in the area of organic semiconducting materials.

Original languageEnglish
Pages (from-to)1959-1969
Number of pages11
JournalJournal of Materials Chemistry C
Volume1
Issue number10
DOIs
Publication statusPublished - Mar 14 2013

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

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