β-Functionalized Push-Pull Porphyrin Sensitizers in Dye-Sensitized Solar Cells: Effect of π-Conjugated Spacers

Masatoshi Ishida, Daesub Hwang, Zhan Zhang, Yung Ji Choi, Juwon Oh, Vincent M. Lynch, Dong Young Kim, Jonanthan L. Sessler, Dongho Kim

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

A series of new β-functionalized push-pull-structured porphyrin dyes were synthesized so as to investigate the effect of the π-conjugated spacer on the performance of dye-sensitized solar cells (DSSCs). Suzuki- and Heck-type palladium-catalyzed coupling methodologies were used to obtain various β-functionalized porphyrins and β-benzoic acid (ZnPHn) and β-vinylbenzoic acid (ZnPVn) derivatives from β-borylated porphyrin precursors. Photophysical studies of the resulting porphyrins revealed a clear dependence on the nature of the β linker. In particular, it was found that a β-vinylene linkage perturbs the electronic structure of the porphyrin core; this is less true for a β-phenyl linkage. Theoretical analyses provided support for the intrinsic intramolecular charge-transfer character of the β-functionalized, push-pull porphyrins of this study. The extent of charge transfer depends on the nature of the β-conjugated linkage. The photovoltaic performances of the cells sensitized with β-phenylenevinylene ZnPVn exhibited higher power conversion efficiency values than those bearing β-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 β-butadiene-linked porphyrin.

Original languageEnglish
Pages (from-to)2967-2977
Number of pages11
JournalChemSusChem
Volume8
Issue number17
DOIs
Publication statusPublished - Sep 1 2015

Fingerprint

porphyrin
Porphyrins
dye
electrolyte
Electrolytes
Charge transfer
acid
Bearings (structural)
Acids
Benzoic Acid
Benzoic acid
effect
solar cell
Dye-sensitized solar cells
palladium
Palladium
iodine
Cobalt
Iodine
Butadiene

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Chemical Engineering(all)
  • Materials Science(all)
  • Energy(all)

Cite this

β-Functionalized Push-Pull Porphyrin Sensitizers in Dye-Sensitized Solar Cells : Effect of π-Conjugated Spacers. / Ishida, Masatoshi; Hwang, Daesub; Zhang, Zhan; Choi, Yung Ji; Oh, Juwon; Lynch, Vincent M.; Kim, Dong Young; Sessler, Jonanthan L.; Kim, Dongho.

In: ChemSusChem, Vol. 8, No. 17, 01.09.2015, p. 2967-2977.

Research output: Contribution to journalArticle

Ishida, M, Hwang, D, Zhang, Z, Choi, YJ, Oh, J, Lynch, VM, Kim, DY, Sessler, JL & Kim, D 2015, 'β-Functionalized Push-Pull Porphyrin Sensitizers in Dye-Sensitized Solar Cells: Effect of π-Conjugated Spacers', ChemSusChem, vol. 8, no. 17, pp. 2967-2977. https://doi.org/10.1002/cssc.201500085
Ishida, Masatoshi ; Hwang, Daesub ; Zhang, Zhan ; Choi, Yung Ji ; Oh, Juwon ; Lynch, Vincent M. ; Kim, Dong Young ; Sessler, Jonanthan L. ; Kim, Dongho. / β-Functionalized Push-Pull Porphyrin Sensitizers in Dye-Sensitized Solar Cells : Effect of π-Conjugated Spacers. In: ChemSusChem. 2015 ; Vol. 8, No. 17. pp. 2967-2977.
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