TY - JOUR
T1 - 1,3‐Bis(2‐thienylmethylene)1‐1H,3H1‐thieno[3,4‐c]thiophene
T2 - A Precursor for a New Low Band Gap Polymer
AU - Hanack, Michael
AU - Schmid, Ulrich
AU - Röhrig, Ursula
AU - Toussaint, Jean‐Marc ‐M
AU - Adant, Christine
AU - Brédas, Jean‐Luc ‐L
PY - 1993/6
Y1 - 1993/6
N2 - A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1H,3H1‐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 1H,3H1‐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.
AB - A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1H,3H1‐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 1H,3H1‐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.
KW - 1H,3H1‐Thieno[3,4‐c]thiophene derivative
KW - Polyarenemethylenes
KW - Polymers, low band gap
UR - http://www.scopus.com/inward/record.url?scp=0342719536&partnerID=8YFLogxK
U2 - 10.1002/cber.19931260633
DO - 10.1002/cber.19931260633
M3 - Article
AN - SCOPUS:0342719536
SN - 0009-2940
VL - 126
SP - 1487
EP - 1491
JO - Chemische Berichte
JF - Chemische Berichte
IS - 6
ER -