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Double-caged fullerene acceptors: effect of alkyl chain length on photovoltaic performanceElectronic supplementary information (ESI) available: Experimental details and mass spectral and NMR data. See DOI: 10.1039/c8tc05971c

We report the synthesis and spectroscopic and electrochemical characterization of the benzyl, C 4 , C 6 , C 8 , C 9 , C 10 , and C 18 n -alkyl esters of double-caged fullerene compounds ( dFR ). Counterintuitively, their solubility depends nonmonotonically on the alkyl chain length with a minimum at...

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Main Authors: Brotsman, Victor A, Rybalchenko, Alexey V, Zubov, Dmitry N, Paraschuk, Dmitry Yu, Goryunkov, Alexey A
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Summary:We report the synthesis and spectroscopic and electrochemical characterization of the benzyl, C 4 , C 6 , C 8 , C 9 , C 10 , and C 18 n -alkyl esters of double-caged fullerene compounds ( dFR ). Counterintuitively, their solubility depends nonmonotonically on the alkyl chain length with a minimum at n -octyl. The series of dFR compounds were tested in organic solar cells (OSCs) as an acceptor material blended with the poly(3-hexylthiophene-2,5-diyl) (P3HT) donor. With the exception of the n -octadecyl derivative, the performance of the P3HT/ dFR solar cells correlates with the solubility of the dFR component, likely due to the improved bulk heterojunction morphology and its favorable effect on J SC via lower series resistance. A peak PCE of 3.0% was found for the n -nonyl compound, thus exceeding other known fullerene oligomers with fused fullerene cages or cross-linked fullerene dimers. The poor performance of compounds with too long alkyl chains like n -octadecyl reflects larger series resistance that results from a higher degree of phase segregation. Alkyl chain length in double-caged fullerene compounds ( dFR ) nonmonotonically correlates with dFR solubility providing best BHJ morphology and photovoltaic performance for the highly-soluble n -nonyl derivative.
ISSN:2050-7526
2050-7534
DOI:10.1039/c8tc05971c