Journal
MACROMOLECULES
Volume 45, Issue 10, Pages 4069-4074Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ma300589k
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Funding
- Office of Science, Office of Basic Energy Sciences, Material Sciences and Engineering Division, of the U.S. Department of Energy [DE-AC02-05CH11231]
- Frechet Various Donors gift fund
- Fondazione Banca del Monte di Lombardia
- National Science Foundation
- Camille and Henry Dreyfus Postdoctoral Program in Environmental Chemistry
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A series of low band gap isothianaphthene-based (ITN) polymers with various electron-withdrawing substituents and intrinsic quinoidal character were synthesized, characterized, and tested in organic photovoltaic (OPV) devices. The three investigated ITN cores contained either ester, imide, or nitrile functionalities and were each synthesized in only four linear steps. The relative electron-withdrawing strength of the three substituents on the ITN moiety was evaluated and correlated to the optical and electronic properties of ITN-based copolymers. The ester- and imide-containing p-type polymers reached device efficiencies as high as 3% in bulk heterojunction blends with phenyl C-61-butyric acid methyl ester (PC61BM), while the significantly electron-deficient nitrile-functionalized polymer behaved as an n-type material with an efficiency of 0.3% in bilayer devices with poly(3-(4-n-octyl)phenylthiophene) (POPT).
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