TY - JOUR
T1 - Dithienopyrrole-quinoxaline/pyridopyrazine donor-acceptor polymers
T2 - Synthesis and electrochemical, optical, charge-transport, and photovoltaic properties
AU - Zhang, Xuan
AU - Shim, Jae Won
AU - Tiwari, Shree Prakash
AU - Zhang, Qing
AU - Norton, Joseph E.
AU - Wu, Pei Tzu
AU - Barlow, Stephen
AU - Jenekhe, Samson A.
AU - Kippelen, Bernard
AU - Brédas, Jean Luc
AU - Marder, Seth R.
PY - 2011/4/7
Y1 - 2011/4/7
N2 - Soluble alternating copolymers of N-(3,4,5-tri-n-dodecyloxyphenyl) dithieno[3,2-b:2′,3′-d]pyrrole donor groups and 2,3-di-n- decylquinoxaline, 2,3-di-n-decylpyrido[3,4-b]pyrazine, 2,3,6,7-tetrakis(n- decyloxy)benzo[a,c]phenazine, or 2,3,6,7-tetrakis(n-decyloxy)dibenzo[f,h] pyrido[4,3-b]quinoxaline acceptors were synthesised using Stille coupling reactions. Experimental absorption maxima in THF range from 645 to 770 nm. These optical data, along with the results of quantum-chemical calculations and electrochemical measurements, show that, as expected, the pyridopyrazine moiety acts as a stronger acceptor than quinoxaline and that the extended species benzophenazine and dibenzopyridoquinoxaline are stronger acceptors than quinoxaline and pyridopyrazine, respectively. Modest average hole mobilities of up to ca. 3.0 × 10-4 cm2 V-1 s -1 were obtained in field-effect transistors. Bulk heterojunction photovoltaic devices made from blends of the benzo[a,c]phenazine-based polymer with 3′-phenyl-3′H-cyclopropa[1,9](C60-I h)[5,6]fullerene-3′-butanoic acid methyl ester (1:3 weight ratio) exhibited average power conversion efficiencies up to 1.4%.
AB - Soluble alternating copolymers of N-(3,4,5-tri-n-dodecyloxyphenyl) dithieno[3,2-b:2′,3′-d]pyrrole donor groups and 2,3-di-n- decylquinoxaline, 2,3-di-n-decylpyrido[3,4-b]pyrazine, 2,3,6,7-tetrakis(n- decyloxy)benzo[a,c]phenazine, or 2,3,6,7-tetrakis(n-decyloxy)dibenzo[f,h] pyrido[4,3-b]quinoxaline acceptors were synthesised using Stille coupling reactions. Experimental absorption maxima in THF range from 645 to 770 nm. These optical data, along with the results of quantum-chemical calculations and electrochemical measurements, show that, as expected, the pyridopyrazine moiety acts as a stronger acceptor than quinoxaline and that the extended species benzophenazine and dibenzopyridoquinoxaline are stronger acceptors than quinoxaline and pyridopyrazine, respectively. Modest average hole mobilities of up to ca. 3.0 × 10-4 cm2 V-1 s -1 were obtained in field-effect transistors. Bulk heterojunction photovoltaic devices made from blends of the benzo[a,c]phenazine-based polymer with 3′-phenyl-3′H-cyclopropa[1,9](C60-I h)[5,6]fullerene-3′-butanoic acid methyl ester (1:3 weight ratio) exhibited average power conversion efficiencies up to 1.4%.
UR - http://www.scopus.com/inward/record.url?scp=79952768541&partnerID=8YFLogxK
U2 - 10.1039/c0jm04290k
DO - 10.1039/c0jm04290k
M3 - Article
AN - SCOPUS:79952768541
SN - 0959-9428
VL - 21
SP - 4971
EP - 4982
JO - Journal of Materials Chemistry
JF - Journal of Materials Chemistry
IS - 13
ER -