Artificial photosynthetic antenna-reaction center complexes based on a hexaphenylbenzene core

Yuichi Terazono, Paul A. Liddell, Vikas Garg, Gerdenis Kodis, Alicia Brune, Michael Hambourger, Ana L Moore, Thomas A Moore, John Devens Gust

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

A hexaphenylbenzene scaffold has been used to organize the components of artificial photosynthetic antennas and antenna-reaction center mimics that feature bis(phenylethynyl)anthracene antenna moieties and porphyrin-fullerene charge-separation units. The five bis(phenylethynyl)-anthracene chromophores absorb in the spectral region around 430-480 nm, where porphyrins have low extinction coefficients but solar irradiance is maximal. The hexaphenylbenzene core was built up by the well-known Diels-Alder reaction of diarylacetylenes with substituted tetraphenylcyclopentadienones. The latter were in turn prepared by condensation of substituted benzils and dibenzyl ketones, allowing flexibility in the design of the substitution pattern on the core. The spacing between the various chromophores is suitable for rapid singlet-singlet energy transfer among antenna moieties and the porphyrin, and the relatively rigid structure of the hexaphenylbenzene limits conformational heterogeneity that could reduce the efficiency of energy and electron transfer. NMR studies reveal a high barrier to rotation of the porphyirn plane relative to the hexaphenylbenzene.

Original languageEnglish
Pages (from-to)706-723
Number of pages18
JournalJournal of Porphyrins and Phthalocyanines
Volume9
Issue number10-11
Publication statusPublished - 2005

Fingerprint

Porphyrins
Antennas
Chromophores
Fullerenes
Rigid structures
Ketones
Scaffolds
Energy transfer
Condensation
Substitution reactions
Nuclear magnetic resonance
Electrons
anthracene

Keywords

  • Hexaphenylbenzene
  • Photoinduced electron transfer
  • Porphyrin
  • Singlet energy transfer
  • Synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Terazono, Y., Liddell, P. A., Garg, V., Kodis, G., Brune, A., Hambourger, M., ... Gust, J. D. (2005). Artificial photosynthetic antenna-reaction center complexes based on a hexaphenylbenzene core. Journal of Porphyrins and Phthalocyanines, 9(10-11), 706-723.

Artificial photosynthetic antenna-reaction center complexes based on a hexaphenylbenzene core. / Terazono, Yuichi; Liddell, Paul A.; Garg, Vikas; Kodis, Gerdenis; Brune, Alicia; Hambourger, Michael; Moore, Ana L; Moore, Thomas A; Gust, John Devens.

In: Journal of Porphyrins and Phthalocyanines, Vol. 9, No. 10-11, 2005, p. 706-723.

Research output: Contribution to journalArticle

Terazono, Y, Liddell, PA, Garg, V, Kodis, G, Brune, A, Hambourger, M, Moore, AL, Moore, TA & Gust, JD 2005, 'Artificial photosynthetic antenna-reaction center complexes based on a hexaphenylbenzene core', Journal of Porphyrins and Phthalocyanines, vol. 9, no. 10-11, pp. 706-723.
Terazono Y, Liddell PA, Garg V, Kodis G, Brune A, Hambourger M et al. Artificial photosynthetic antenna-reaction center complexes based on a hexaphenylbenzene core. Journal of Porphyrins and Phthalocyanines. 2005;9(10-11):706-723.
Terazono, Yuichi ; Liddell, Paul A. ; Garg, Vikas ; Kodis, Gerdenis ; Brune, Alicia ; Hambourger, Michael ; Moore, Ana L ; Moore, Thomas A ; Gust, John Devens. / Artificial photosynthetic antenna-reaction center complexes based on a hexaphenylbenzene core. In: Journal of Porphyrins and Phthalocyanines. 2005 ; Vol. 9, No. 10-11. pp. 706-723.
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