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Proton-Coupled Self-Assembly of a Porphyrin-Naphthalenediimide Dyad

Authors

  • Siyu Tu,

    1. Department of Chemistry, The Ohio State University, 100W. 18th. Avenue, Columbus, Ohio 43210 (USA)
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  • Se Hye Kim,

    1. Department of Chemistry, The Ohio State University, 100W. 18th. Avenue, Columbus, Ohio 43210 (USA)
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  • Jojo Joseph,

    1. Department of Chemistry and The Center for Laser and Optical Spectroscopy, The University of Akron, Akron, Ohio 44325-3601 (USA)
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  • Prof. David A. Modarelli,

    Corresponding author
    1. Department of Chemistry and The Center for Laser and Optical Spectroscopy, The University of Akron, Akron, Ohio 44325-3601 (USA)
    • Department of Chemistry and The Center for Laser and Optical Spectroscopy, The University of Akron, Akron, Ohio 44325-3601 (USA)
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  • Prof. Jon R. Parquette

    Corresponding author
    1. Department of Chemistry, The Ohio State University, 100W. 18th. Avenue, Columbus, Ohio 43210 (USA)
    • Department of Chemistry, The Ohio State University, 100W. 18th. Avenue, Columbus, Ohio 43210 (USA)
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Abstract

The construction of an n–p heterojunction through the self-assembly of a dyad based on tetraphenylporphyrin (TPP) and 1,4,5,8-naphthalenedimide (NDI) (1) is described. Proton transfer from the lysine head group of 1 to the porphyrin ring occurs concomitantly with self-assembly into 1D nanorods in CHCl3. TEM and AFM studies showed that the nanorods are formed by the lateral and vertical fusion of multilameller vesicles into networks and hollow ribbons, respectively. These intermediate structures transitioned to nanorods over the course of 4–6 days. Time-resolved spectroscopy revealed that photoinduced charge separation occurs with rate constants that depend on the nature of the aggregation.

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