End-cap Group Engineering of a Small Molecule Non-Fullerene Acceptor: The Influence of Benzothiophene DioxideClick to copy article linkArticle link copied!
- Hongda CaoHongda CaoDepartment of Chemistry and Biochemistry, The University of Alabama, Tuscaloosa, Alabama 35487, United StatesMore by Hongda Cao
- Nicole BauerNicole BauerDepartment of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United StatesMore by Nicole Bauer
- Chao PangChao PangState Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing, Jiangsu 210009, P. R. ChinaCenter for Materials for Information Technology (MINT), The University of Alabama, Tuscaloosa, Alabama 35487, United StatesMore by Chao Pang
- Jeromy RechJeromy RechDepartment of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United StatesMore by Jeromy Rech
- Wei YouWei YouDepartment of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United StatesMore by Wei You
- Paul A. Rupar*Paul A. Rupar*E-mail: [email protected]Department of Chemistry and Biochemistry, The University of Alabama, Tuscaloosa, Alabama 35487, United StatesMore by Paul A. Rupar
Abstract
In this study, a sulfonyl-containing end-capping moiety, benzothiophene dioxide, was selected to prepare the nonfullerene acceptor ITBC. ITBC has an acceptor–donor–acceptor (A-D-A) structure, with indacenodithieno[3,2-b]thiophene (IDTT) as the electron-rich core moiety. The strong electron-withdrawing sulfonyl acceptor units leads to extended UV–vis absorption into the near-IR region and relatively low frontier molecular orbital energy levels (LUMO/HOMO: −4.13 eV/–5.61 eV) with a narrow bandgap of 1.48 eV. These values compare favorably to the well-studied small molecule acceptor 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile end-capped indacenodithieno[3,2-b]thiophene (ITIC). A power conversion efficiency of 4.17% was achieved by fabricating organic solar cells with the fluorinated conjugated polymer FTAZ as the donor and ITBC as the acceptor. These results indicate that benzothiophene dioxide is a novel electron-withdrawing end-capping unit for ITBC, and can be used as an electron acceptor for organic solar cells.
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