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A molecular modeling study of complex formation and self-aggregation behavior of a porphyrin–β-cyclodextrin conjugate

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Abstract

This paper reports a molecular modeling study of complex formation and aggregation behavior of a supramolecular system comprising three different moieties forming two distinct molecules. One molecule is a phenol derivative of porphyrin conjugated to a macrocyclic oligosaccharide, β-cyclodextrin (β-CD), and the other is 1-adamantanol (ADM). The inclusion complex of the latter molecule with the porphyrin–β-cyclodextrin (β-CD) conjugate, and the dimeric aggregates of the conjugate both in the presence and in the absence of the guest are investigated through molecular mechanics and molecular dynamics methods in vacuo, since the systems are scarcely soluble in polar solvents. In this way, we can find the most likely geometry of the complexes or aggregates and characterize the competitive inclusion behavior of ADM and of a porphyrin phenol within the β-CD cavity in terms of the various energy contributions stabilizing the resulting aggregates and/or inclusion complexes.

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Authors and Affiliations

  1. Dipartimento di Chimica, Materiali e Ingegneria Chimica “G. Natta”, Politecnico di Milano, Milan, Italy

    Giuseppina Raffaini & Fabio Ganazzoli

  2. INSTM, Unità Politecnico, Piazza Leonardo da Vinci 32, 20133, Milan, Italy

    Giuseppina Raffaini & Fabio Ganazzoli

Authors
  1. Giuseppina Raffaini
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  2. Fabio Ganazzoli
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Correspondence to Giuseppina Raffaini.

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Raffaini, G., Ganazzoli, F. A molecular modeling study of complex formation and self-aggregation behavior of a porphyrin–β-cyclodextrin conjugate. J Incl Phenom Macrocycl Chem 76, 213–221 (2013). https://doi.org/10.1007/s10847-012-0193-x

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  • DOI: https://doi.org/10.1007/s10847-012-0193-x

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