Self-assembled zinc chlorin rod antennae powered by peripheral light-harvesting chromophores

Cornelia Röger, Y. Miloslavina, Doris Brunner, Alfred R. Holzwarth, Frank Würthner

Research output: Contribution to journalArticle

98 Citations (Scopus)

Abstract

The multichromophoric dyads 1, 2 and triad 3 have been synthesized by coupling of the appropriately functionalized chlorin derivative with naphthalene diimide dyes through esterification, and subsequent metalation of the chlorin center with zinc acetate. The self-assembly properties of naphthalene diimide (NDI)-zinc chlorin (ZnChl) dyads 1, 2 and triad 3 have been studied in nonpolar, aprotic solvents by UV-vis, CD, and steady-state emission spectroscopy, revealing formation of rod-like structures by noncovalent interactions of zinc chlorin units, while the appended naphthalene diimide dyes do not aggregate at the periphery of the rod antennae. In all these systems, photoexcitation of the enveloping naphthalene diimides at 540 and 620 nm, respectively, leads to highly efficient energy-transfer processes (FRET; φET ≥ 0.99) to the inner zinc chlorin backbone, as explored by time-resolved fluorescence spectroscopy on the picosecond time scale. The efficiencies of zinc chlorin rod aggregates for the harvesting of solar light are markedly increased from 26% for dyad 2 up to 63% for triad 3, compared to the LH capacity of the monochromophoric aggregates of model system ZnChl 6a. Thus, with the self-assembled zinc chlorin rod antenna based on triad 3, a highly efficient artificial LH system has been achieved.

Original languageEnglish
Pages (from-to)5929-5939
Number of pages11
JournalJournal of the American Chemical Society
Volume130
Issue number18
DOIs
Publication statusPublished - May 7 2008

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Chromophores
Zinc
Antennas
Light
Naphthalene
Coloring Agents
Zinc Acetate
Dyes
Photoexcitation
Esterification
Fluorescence Spectrometry
Energy Transfer
Fluorescence spectroscopy
Emission spectroscopy
Energy transfer
Self assembly
zinc chlorin
Spectrum Analysis
Derivatives
naphthalenediimide

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Self-assembled zinc chlorin rod antennae powered by peripheral light-harvesting chromophores. / Röger, Cornelia; Miloslavina, Y.; Brunner, Doris; Holzwarth, Alfred R.; Würthner, Frank.

In: Journal of the American Chemical Society, Vol. 130, No. 18, 07.05.2008, p. 5929-5939.

Research output: Contribution to journalArticle

Röger, Cornelia ; Miloslavina, Y. ; Brunner, Doris ; Holzwarth, Alfred R. ; Würthner, Frank. / Self-assembled zinc chlorin rod antennae powered by peripheral light-harvesting chromophores. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 18. pp. 5929-5939.
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