Reducing regioisomers of fullerene-bisadducts by tether-directed remote functionalization: investigation of electronically and sterically isomeric effects on bulk-heterojunction solar cells

ACS Applied Materials & Interfaces
Ming-Hung LiaoYen-Ju Cheng

Abstract

C60 bis-adduct containing a mixture of regio-isomers with different LUMO energy levels and steric geometries could greatly affect the morphological and bulk properties. To investigate the regio-isomer effect on solar cell performance, we have successfully designed and synthesized a regio-selective 4-acetatephenyl-4'-methylphenylmethano C60 bis-adduct (S-APM-CBA) by "tether-directed remote functionalization" strategy and a random 4-acetatephenyl-4'-methylphenylmethano C60 bis-adduct denoted as R-APM-CBA by traditional cyclopropanation. The dramatic reduction in the number of regio-isomers in S-APM-CBA is confirmed by the (1)H NMR and HPLC measurements and theoretical calculation. Compared to the R-APM-CBA-based device with a Jsc of 6.63 mA/cm(2), an FF of 44.3% and a PCE of 2.46%, the device using S-APM-CBA yielded a much lower Jsc of 1.48 mA/cm(2), an FF of 32.2%, and a PCE of 0.38%. Consistently, the electron-only device using S-AMP-CBA exhibited lower electron mobility than the R-AMP-CBA-based device. These results imply that the electronic shallow-trap effect ascribed to the LUMO energy variations turned out to be insignificant in the AMP-CBA system. The lower efficiency and mobility of S-AMP-CBA might due to the assumption ...Continue Reading

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Citations

Sep 5, 2015·Organic & Biomolecular Chemistry·Bolong ZhangWallace W H Wong
May 21, 2015·Chemical Communications : Chem Comm·Bolong ZhangWallace W H Wong
Jan 15, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Marco CariniAurelio Mateo-Alonso
Dec 23, 2016·The Journal of Organic Chemistry·Maira R CerónLuis A Echegoyen
Jun 25, 2016·Beilstein Journal of Organic Chemistry·Bolong ZhangWallace Wing Ho Wong
May 20, 2015·Journal of the American Chemical Society·Maira R CerónLuis Echegoyen
Jul 19, 2019·Accounts of Chemical Research·Tomokazu Umeyama, Hiroshi Imahori

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