Journal
CHEMSUSCHEM
Volume 8, Issue 17, Pages 2967-2977Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201500085
Keywords
cross-coupling; density functional calculations; donor-acceptor systems; porphyrins; solar cells
Funding
- Global Frontier R&D Program on Center for Multiscale Energy System - National Research Foundation under the Ministry of Science, ITC Future, Korea [2012-8-2081]
- United States National Science Foundation [CHE-1402004]
- Korea Institute of Science and Technology Institutional Program [2E25371]
- Robert A. Welch Foundation [F-1018]
- Japan Society for the Promotion of Science [26810024]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1402004] Funding Source: National Science Foundation
- Grants-in-Aid for Scientific Research [26810024] Funding Source: KAKEN
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A series of new beta-functionalized push-pull-structured porphyrin dyes were synthesized so as to investigate the effect of the p-conjugated spacer on the performance of dye-sensitized solar cells (DSSCs). Suzuki-and Heck-type palladium-catalyzed coupling methodologies were used to obtain various beta-functionalized porphyrins and beta-benzoic acid (ZnPHn) and beta-vinylbenzoic acid (ZnPVn) derivatives from beta-borylated porphyrin precursors. Photophysical studies of the resulting porphyrins revealed a clear dependence on the nature of the beta linker. In particular, it was found that a beta-vinylene linkage perturbs the electronic structure of the porphyrin core; this is less true for a beta-phenyl linkage. Theoretical analyses provided support for the intrinsic intramolecular charge-transfer character of the beta-functionalized, push-pull porphyrins of this study. The extent of charge transfer depends on the nature of the beta-conjugated linkage. The photovoltaic performances of the cells sensitized with beta-phenylenevinylene ZnPVn exhibited higher power conversion efficiency values than those bearing beta-phenyl linkages (ZnPHn). This was ascribed to differences in light-harvesting efficiency. Furthermore, compared to the use of a standard iodine-based electrolyte, the DSSC performance of cells made from the present porphyrins was improved by more than 1% upon using a cobalt(II/III)-based electrolyte. Under standard AM 1.5 illumination, the highest efficiency, 8.2 %, was obtained by using cells made from the doubly beta-butadiene-linked porphyrin.
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