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Unveiling the nature of supramolecular crown ether–C 60 interactions

2015; Royal Society of Chemistry; Volume: 6; Issue: 8 Linguagem: Inglês

10.1039/c5sc00850f

2041-6539

Luis Moreira, Joaquín Calbo, Rafael M. Krick Calderón, José Santos, Beatriz M. Illescas, Juan Aragó, Jean‐François Nierengarten, Dirk M. Guldi, Enrique Ortı́, Nazario Martı́n,

Boron and Carbon Nanomaterials Research

A series of exTTF-(crown ether)2 receptors, designed to host C60, has been prepared. The size of the crown ether and the nature of the heteroatoms have been systematically changed to fine tune the association constants. Electrochemical measurements and transient absorption spectroscopy assisted in corroborating charge transfer in the ground state and in the excited state, leading to the formation of radical ion pairs featuring lifetimes in the range from 12 to 21 ps. To rationalize the nature of the exTTF-(crown ether)2·C60 stabilizing interactions, theoretical calculations have been carried out, suggesting a synergetic interplay of donor-acceptor, π-π, n-π and CH···π interactions, which is the basis for the affinity of our novel receptors towards C60.