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Synthesis, Characterization, and Electron‐Transport Properties of a π‐Conjugated Heteromacrocycle: A Selenium‐Bridged Neutral Annulene
Author(s) -
Liu Hang,
Qin Yunke,
Xu Wei,
Zhu Daoben
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402157
Subject(s) - annulene , chemistry , conjugated system , aromaticity , thermostability , electron mobility , carbon fibers , selenium , electrochemistry , crystallography , polymer , molecule , stereochemistry , organic chemistry , optoelectronics , materials science , electrode , composite number , composite material , enzyme
An aromatic heteromacrocycle, selenium bridged neutral annulene 5,16‐diphenyltetraselenolo[22]annulene[2,1,2,1] (DPTSA) was synthesized through a convenient four‐step procedure. DPTSA is a symmetrical macrocyclic architecture consisting of four selenophene units linked with unsaturated carbon–carbon bonds. DPTSA was shown to have high aromaticity by 1 H NMR and UV/vis absorption spectra. Its electrochemical properties and thermostability were studied. A thin‐film transistor based on DPTSA was fabricated to evaluate the possibility of its application in organic field‐effect transistors (OFETs). DPTSA performed as a p ‐type semiconductor with the best hole mobility of 2.8×10 −3 cm 2 V −1 S −1 and the on/off ratio of 1.0×10 5 . The thin‐film morphology of devices based on DPTSA was also characterized to preliminarily reveal the structure‐property relationships.