Issue 28, 2011

Thiophene–benzothiadiazole–thiophene (D–A–D) based polymers: effect of donor/acceptor moieties adjacent to D–A–D segment on photophysical and photovoltaic properties

Abstract

New push–pull copolymers based on thiophene (donor) and benzothiadiazole (acceptor) units, poly[4,7-bis(3-dodecylthiophene-2-yl) benzothiadiazole-co-thiophene] (PT3B1) and poly[4,7-bis(3-dodecylthiophene-2-yl) benzothiadiazole-co-benzothiadiazole] (PT2B2), are designed and synthesized via Stille and Suzuki coupling routes respectively. Gel permeation chromatography shows the number average molecular weights are 31 100 and 8400 g mol−1 for the two polymers, respectively. Both polymers have shown absorption throughout a wide range of the UV-vis region, from 300 to 650 nm. A significant red shift of the absorption edge is observed in thin films compared to solution of the copolymers; the optical band gap is in the range of 1.7 to 1.8 eV. Cyclic voltammetry indicates reversible oxidation and reduction processes with HOMO energy levels calculated to be in the range of 5.2 to 5.4 eV. Upon testing both materials for organic field-effect transistors (OFETs), PT3B1 showed a hole mobility of 6.1 × 10−4 cm2 V−1 s−1, while PT2B2 did not show any field effect transport. Both copolymers displayed a photovoltaic response when combined with a methanofullerene as an electron acceptor. The best performance was achieved when the copolymer PT3B1 was blended with [70]PCBM in a 1 : 4 ratio, exhibiting a short-circuit current of 7.27 mA cm−2, an open circuit voltage of 0.85 V, and a fill factor of 41% yielding a power conversion efficiency of 2.54% under simulated air mass (AM) 1.5 global (1.5 G) illumination conditions (100 mW cm−2). Similar devices utilizing PT2B2 in place of PT3B1 demonstrated reduced performance with a short-circuit current of 4.8 mA cm−2, an open circuit voltage of 0.73 V, and a fill factor of 30% resulting in a power conversion efficiency of roughly 1.06%.

Graphical abstract: Thiophene–benzothiadiazole–thiophene (D–A–D) based polymers: effect of donor/acceptor moieties adjacent to D–A–D segment on photophysical and photovoltaic properties

Supplementary files

Article information

Article type
Paper
Submitted
14 Feb 2011
Accepted
20 Apr 2011
First published
07 Jun 2011

J. Mater. Chem., 2011,21, 10532-10541

Thiophenebenzothiadiazolethiophene (D–A–D) based polymers: effect of donor/acceptor moieties adjacent to D–A–D segment on photophysical and photovoltaic properties

P. Sonar, E. L. Williams, S. P. Singh and A. Dodabalapur, J. Mater. Chem., 2011, 21, 10532 DOI: 10.1039/C1JM10649J

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