Litcius/Paper detail

Heptagon‐Containing Nanographene Embedded into [10]Cycloparaphenylene

Juan P. Mora‐Fuentes, Marcos D. Codesal, Marco Reale, Carlos M. Cruz, Vicente G. Jiménez, Alice Sciortino, M. Cannas, Fabrizio Messina, Víctor Blanco, Araceli G. Campaña

2023Angewandte Chemie International Edition32 citationsDOIOpen Access PDF

Abstract

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 C 60 and C 70 , with remarkably large binding constants (ca. 10 7 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.

Topics & Concepts

PhotoexcitationFullereneSupramolecular chemistryNanosecondFemtosecondDerivative (finance)CorannuleneMaterials scienceCharge (physics)ChemistryPhotochemistryMoleculeChemical physicsOrganic chemistryExcited stateLaserAtomic physicsFinancial economicsOpticsPhysicsEconomicsQuantum mechanicsFullerene Chemistry and ApplicationsSynthesis and Properties of Aromatic CompoundsGraphene research and applications