Novel zinc phthalocyanine-benzoquinone rigid dyad and its photoinduced electron transfer properties

Chi Hang Lee, Jiangchang Guo, Lin X Chen, Braja K. Mandal

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

(Chemical Equation Presented) While preparing the first structurally rigid zinc phthalocyanine-benzoquinone (ZnPc-BQ) dyad as a model for photoinduced charge separation mimicking natural photosynthesis, a convenient method is developed for in situ generation of a benzoquinone chromophore in the dyad using an iso-butyryl mask. The dyad has no rotamers and possesses a fixed distance between ZnPc and BQ moieties (center-to-center and edge-to-edge distances are 9.40 and 2.14 Å, respectively). The dyad displays unusual electronic perturbation in the ground state, resulting from the interactions between Pc and BQ, and exhibits photoinduced electron transfer with a lifetime of 40 ps of the charged separated states. The steady-state fluorescence and electrochemical behavior of the dyad are evaluated. This study opens a route to subsequent dyads, triads, and complex architectures of electron donor-acceptor arrays with rigid structures and long charge separation states.

Original languageEnglish (US)
Pages (from-to)8219-8227
Number of pages9
JournalJournal of Organic Chemistry
Volume73
Issue number21
DOIs
StatePublished - Nov 7 2008

ASJC Scopus subject areas

  • Organic Chemistry

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