TY - JOUR
T1 - Synthesis and electronic properties of 4- cyanophenylvinylenedithiathiophene
T2 - An EDOT derivative
AU - Sucsoran, Oznur
AU - Bekiroglu, Somer
AU - Ozturk, Turan
AU - Ertas, Erdal
PY - 2012/2
Y1 - 2012/2
N2 - Synthesis of 4-cyanophenylvinylenedithiathiophene, which is an analogue of ethylenedioxythiophene (EDOT), has been described. The synthesis was achieved by applying 1,8-diketone ring formation reaction occurring between 1,8-diketone and phosphorus decasulfide in boiling toluene. The target compound was characterized by cyclic voltammetry (CV), UV spectroscopy, and theoretical studies. Unlike the analogues similarly carrying phenyl groups substituted with other functional groups such as -OMe, -Br, -NO 2, neither electrochemical polymerization attempts nor chemical polymerization efforts with ferric chloride(III) (FeCl 3) succeeded in yielding any products. Results of spin density calculations revealed that the molecule did not have enough electron spin densities at the "α" carbons of the thiophene part. Moreover, during the polymerization attempt with FeCl 3, as the nitrile nitrogen could form complex with iron, spin density calculation was also performed for protonated form of the monomer, which indicated that the "α" carbons of the molecule had even lower spin densities.
AB - Synthesis of 4-cyanophenylvinylenedithiathiophene, which is an analogue of ethylenedioxythiophene (EDOT), has been described. The synthesis was achieved by applying 1,8-diketone ring formation reaction occurring between 1,8-diketone and phosphorus decasulfide in boiling toluene. The target compound was characterized by cyclic voltammetry (CV), UV spectroscopy, and theoretical studies. Unlike the analogues similarly carrying phenyl groups substituted with other functional groups such as -OMe, -Br, -NO 2, neither electrochemical polymerization attempts nor chemical polymerization efforts with ferric chloride(III) (FeCl 3) succeeded in yielding any products. Results of spin density calculations revealed that the molecule did not have enough electron spin densities at the "α" carbons of the thiophene part. Moreover, during the polymerization attempt with FeCl 3, as the nitrile nitrogen could form complex with iron, spin density calculation was also performed for protonated form of the monomer, which indicated that the "α" carbons of the molecule had even lower spin densities.
KW - 4-Cyanophenylvinylenedithiathiophene
KW - Ethylenedioxythiophene
KW - Phosphorus decasulfide (P S )
KW - Radical spin density dithiin
UR - http://www.scopus.com/inward/record.url?scp=84855873452&partnerID=8YFLogxK
U2 - 10.1016/j.synthmet.2011.11.007
DO - 10.1016/j.synthmet.2011.11.007
M3 - Article
AN - SCOPUS:84855873452
SN - 0379-6779
VL - 162
SP - 49
EP - 53
JO - Synthetic Metals
JF - Synthetic Metals
IS - 1-2
ER -