Inclusion of polymethine cyanine dyes in the cavity of macrocyclic receptors is an effective strategy to alter their absorption and emission behavior in aqueous solution. In this paper, the effect of the host-guest interaction between cucurbit[8]uril (CB[8]) and a model trimethine indocyanine (Cy3) on dye spectral properties and aggregation in water is investigated. Solution studies, performed by a combination of spectroscopic and calorimetric techniques, indicate that the addition of CB[8] disrupts Cy3 aggregates leading to the formation of a 1:1 host-guest complex with an association constant of 1.5 × 10 6 M -1 . At concentrations suitable for NMR experiments, the slow formation of a supramolecular polymer was observed, followed by precipitation. Single crystals X-ray structure elucidation confirmed the formation of a polymer with 1:1 stoichiometry in the solid state.

Encapsulation of trimethine cyanine in cucurbit[8]uril: solution versus solid-state inclusion behavior / Soavi, Giuseppe; Pedrini, Alessandro; Das, Anjali Devi; Terenziani, Francesca; Pinalli, Roberta; Hickey, Neal; Medagli, Barbara; Geremia, Silvano; Dalcanale, Enrico. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 28:(2022). [10.1002/chem.202200185]

Encapsulation of trimethine cyanine in cucurbit[8]uril: solution versus solid-state inclusion behavior

Soavi, Giuseppe;Pedrini, Alessandro;Das, Anjali Devi;Terenziani, Francesca;Pinalli, Roberta;Dalcanale, Enrico
2022-01-01

Abstract

Inclusion of polymethine cyanine dyes in the cavity of macrocyclic receptors is an effective strategy to alter their absorption and emission behavior in aqueous solution. In this paper, the effect of the host-guest interaction between cucurbit[8]uril (CB[8]) and a model trimethine indocyanine (Cy3) on dye spectral properties and aggregation in water is investigated. Solution studies, performed by a combination of spectroscopic and calorimetric techniques, indicate that the addition of CB[8] disrupts Cy3 aggregates leading to the formation of a 1:1 host-guest complex with an association constant of 1.5 × 10 6 M -1 . At concentrations suitable for NMR experiments, the slow formation of a supramolecular polymer was observed, followed by precipitation. Single crystals X-ray structure elucidation confirmed the formation of a polymer with 1:1 stoichiometry in the solid state.
Encapsulation of trimethine cyanine in cucurbit[8]uril: solution versus solid-state inclusion behavior / Soavi, Giuseppe; Pedrini, Alessandro; Das, Anjali Devi; Terenziani, Francesca; Pinalli, Roberta; Hickey, Neal; Medagli, Barbara; Geremia, Silvano; Dalcanale, Enrico. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 28:(2022). [10.1002/chem.202200185]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2917576
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