Synthesis and Photophysics of a Red-Light Absorbing Supramolecular Chromophore System

Authors

  • Jeroen A. Rombouts,

    1. Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
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  • Janneke Ravensbergen,

    1. Department of Biophysics, VU University Amsterdam, De Boelelaan 1081, 1081 HV Amsterdam (The Netherlands)
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  • Dr. Raoul N. Frese,

    1. Department of Biophysics, VU University Amsterdam, De Boelelaan 1081, 1081 HV Amsterdam (The Netherlands)
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  • Dr. John T. M. Kennis,

    1. Department of Biophysics, VU University Amsterdam, De Boelelaan 1081, 1081 HV Amsterdam (The Netherlands)
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  • Dr. Andreas W. Ehlers,

    1. Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
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  • Dr. J. Chris Slootweg,

    1. Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
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  • Dr. Eelco Ruijter,

    1. Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
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  • Prof. Dr. Koop Lammertsma,

    Corresponding author
    1. Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    • Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)===

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  • Prof. Dr. Romano V. A. Orru

    Corresponding author
    1. Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
    • Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)===

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Abstract

In search of supramolecular antenna systems for light-harvesting applications, we report on a short and effective synthesis of a fused NDI–zinc–salphen-based chromophore (salphen = bis-salicylimide phenylene) and its photophysical properties. A supramolecular recognition motif is embedded into the chromophoric π-system of this compound. The fused π-chromophore behaves as one pigment, absorbs light between 600 and 750 nm and displays a modest Stokes shift. Upon binding pyridines, the compound (DATZnS) does not change its redox potentials, does not undergo any internal excited state quenching and does not appreciably alter its excited state lifetime. These notable properties define DATZnS as an alternative to porphyrin-based components used in supramolecular light-harvesting architectures.

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