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 that the most probable trans-4-III isomer in S-AMP-CBA prevents the intermolecular facial contact of fullerenes, thereby hindering the electron transporting. Furthermore, the nanomorphology of S-AMP-CBA and R-AMP-CBA active layers could be different because of their different three-dimensional structures. This research demonstrated that steric effect of regio-isomers in a given C60 bis-adduct is more crucial than electronic shallow-trap effect.
A new cross-linkable fullerene material, bis(2-(trichlorosilyl)propyl)-malonate C 60 (TSMC), functionalized with two trichlorosilane groups, was easily synthesized by Pt-catalyzed olefin hydrosilylation. By making use of facile hydrolysis of the trichlorosilyl moieties, TSMC can be spontaneously self-assembled and cross-linked on the TiO x surface by a simple spin-coating processing without the aid of photoirradiation or post-thermal treatments. The rapid formation of self-assembled and crosslinked TSMC (SA-C-TSMC) effectively passivates the residual hydroxyl groups on the TiO x surface. More significantly, the solvent-resistant TSMC network features a nanostructured surface to provide extra charge-generating interfacial area and straight electron transport pathways. The device (ITO/TiO x /SA-C-TSMC/P3HT:PC 61 BM (1:1, w/w)/PEDOT:PSS/Ag) with this C 60 interlayer exhibited an efficiency of 3.9% which greatly outperformed the device without this layer. Furthermore, the strategy can also be effectively applied to the device (ITO/TiO x /PDITTDTBT:PC 71 BM(1:4, w/w)/MoO x /Ag) incorporating a conjugated polymer, poly(diindenothiophene-alt-dithienylbenzothiadizole) copolymer (PDITTDTBT). This device delivered a high efficiency of 5.8% which represents a 35% enhancement over the device without SA-C-TSMC. This new generation of trichlorosilane-based fullerene offers an easy and accelerated processing technique to produce efficient and cost-effective inverted solar cells.
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