Artificial photosynthetic reaction centers with carotenoid antennas

Stephanie L. Gould, Gerdenis Kodis, Paul A. Liddell, Rodrigo E. Palacios, Alicia Brune, Devens Gust, Thomas A. Moore, Ana L. Moore

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Two reaction center-antenna models based on a purpurin macrocycle linked to a C60 and to a carotenoid polyene have been synthesized. In these systems the C60 moiety is the primary electron acceptor, the purpurin is the primary electron donor and the carotenoid moiety acts both as an antenna and secondary electron donor. Formation of the initial charge separated state, C-Pur+-C60-, following excitation with light absorbed by either the purpurin or C60 takes place on the 10 ps time scale. The final charge separated state, C+-Pur-C60 -, is formed in one of the compounds with a quantum yield of 32% based upon light absorbed by the carotenoid. In order to function as an antenna, the carotenoid pigment must be electronically coupled to the purpurin. The purpurin C ring provides an excellent framework for locating a carotenoid polyene in partial conjugation with the macrocycle, leading to a relatively strong electronic communication between the chromophores; functionalization of a meso position of the purpurin provides a site for the covalent attachment of C60.

Original languageEnglish
Pages (from-to)2074-2096
Number of pages23
JournalTetrahedron
Volume62
Issue number9
DOIs
Publication statusPublished - Feb 27 2006

Keywords

  • Antenna
  • C as primary electron acceptor
  • Carotenoid
  • Energy transfer
  • Photoinduced electron transfer
  • Porphyrin
  • Purpurin
  • Pyrroles

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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