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Synthesis of a donor–acceptor heterodimer via trifunctional completive self-sorting

Author

Listed:
  • Sunit Kumar

    (Uniwersytet Wrocławski)

  • Yogesh Kumar Maurya

    (Uniwersytet Wrocławski)

  • Tadeusz Lis

    (Uniwersytet Wrocławski)

  • Marcin Stępień

    (Uniwersytet Wrocławski)

Abstract

Selective self-assembly of heterodimers consisting of two non-identical subunits plays important roles in Nature but is rarely encountered in synthetic supramolecular systems. Here we show that photocleavage of a donor–acceptor porphyrin complex produces an heterodimeric structure with surprising selectivity. The system forms via a multi-step sequence that starts with an oxidative ring opening, which produces an equimolar mixture of two isomeric degradation products (zinc(II) bilatrien-abc-ones, BTOs). These two isomers are susceptible to water addition, yielding the corresponding zinc(II) 15-hydroxybiladien-ab-ones (HBDOs). However, in the photocleavage experiment only one HBDO isomer is formed, and it quantitatively combines with the remaining BTO isomer. The resulting heterodimer is stabilized by a Zn–O coordination bond and extended dispersion interactions between the overlapping π-surfaces of the monomers. The observed selectivity can be seen as a case of completive self-sorting, simultaneously controlled by three types of complementary interactions.

Suggested Citation

  • Sunit Kumar & Yogesh Kumar Maurya & Tadeusz Lis & Marcin Stępień, 2022. "Synthesis of a donor–acceptor heterodimer via trifunctional completive self-sorting," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30859-7
    DOI: 10.1038/s41467-022-30859-7
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