We report the synthesis and characterization of a novel type of nanohoop, consisting of a cycloparaphenylene derivative incorporating a curved heptagon-containing π-extended polycyclic aromatic hydrocarbon (PAH) unit. We demonstrate that this new macrocycle behaves as a supramolecular receptor of curved π-systems such as fullerenes C60 and C70, with remarkably large binding constants (ca. 107 M−1), as estimated by fluorescence measurements. Nanosecond and femtosecond spectroscopic analysis show that these host-guest complexes are capable of quasi-instantaneous charge separation upon photoexcitation, due to the ultrafast charge transfer from the macrocycle to the complexed fullerene. These results demonstrate saddle-shaped PAHs with dibenzocycloheptatrienone motifs as structural components for new macrocycles displaying molecular receptor abilities and versatile photochemical responses with promising electron-donor properties in host-guest complexes.

Mora-Fuentes J.P., Codesal M.D., Reale M., Cruz C.M., Jimenez V.G., Sciortino A., et al. (2023). Heptagon-Containing Nanographene Embedded into [10]Cycloparaphenylene. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, e202301356 [10.1002/anie.202301356].

Heptagon-Containing Nanographene Embedded into [10]Cycloparaphenylene

Reale M.;Sciortino A.;Cannas M.;Messina F.;
2023-03-21

Abstract

We report the synthesis and characterization of a novel type of nanohoop, consisting of a cycloparaphenylene derivative incorporating a curved heptagon-containing π-extended polycyclic aromatic hydrocarbon (PAH) unit. We demonstrate that this new macrocycle behaves as a supramolecular receptor of curved π-systems such as fullerenes C60 and C70, with remarkably large binding constants (ca. 107 M−1), as estimated by fluorescence measurements. Nanosecond and femtosecond spectroscopic analysis show that these host-guest complexes are capable of quasi-instantaneous charge separation upon photoexcitation, due to the ultrafast charge transfer from the macrocycle to the complexed fullerene. These results demonstrate saddle-shaped PAHs with dibenzocycloheptatrienone motifs as structural components for new macrocycles displaying molecular receptor abilities and versatile photochemical responses with promising electron-donor properties in host-guest complexes.
21-mar-2023
Settore FIS/01 - Fisica Sperimentale
Mora-Fuentes J.P., Codesal M.D., Reale M., Cruz C.M., Jimenez V.G., Sciortino A., et al. (2023). Heptagon-Containing Nanographene Embedded into [10]Cycloparaphenylene. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, e202301356 [10.1002/anie.202301356].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/588259
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