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1,3‐Bis(2‐thienylmethylene)1‐1 H ,3 H 1‐thieno[3,4‐ c ]thiophene: A Precursor for a New Low Band Gap Polymer
Author(s) -
Hanack Michael,
Schmid Ulrich,
Röhrig Ursula,
Toussaint JeanMarc,
Adant Christine,
Brédas JeanLuc
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260633
Subject(s) - chemistry , thiophene , knoevenagel condensation , cyclic voltammetry , mndo , sulfoxide , band gap , pseudopotential , crystallography , medicinal chemistry , photochemistry , stereochemistry , molecule , electrochemistry , organic chemistry , electrode , catalysis , physics , quantum mechanics , condensed matter physics
A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1 H ,3 H 1‐thieno‐[3,4‐ c ]thiophene( 9 ), for polyarenemethylenes (PAM), which are predicted to be low band gap polymers, is obtained by a Knoevenagel‐type condensation of 1 H ,3 H 1‐thieno[3,4‐ c ]thiophene 2‐oxide ( 7 ) with 2‐thiophenecarbaldehyde followed by reduction of the intermediate sulfoxide 8 with 2‐chloro‐1,3,2‐benzodioxaphosphole. Several investigations with cyclic voltammetry and UV‐Vis‐NIR spectroelectrochemistry (SEC) are carried out on 9 . The experimental data are compared with the results of electronic band structure calculated on the basis of an MNDO‐optimized geometric structure by VEH pseudopotential method.