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A Green Fluorescent Nitrogen‐Doped Aromatic Belt Containing a [6]Cycloparaphenylene Skeleton

Fan Zhang, Xu‐Sheng Du, Da‐Wei Zhang, Yinfeng Wang, Haiyan Lu, Chuan‐Feng Chen

2021Angewandte Chemie10 citationsDOI

Abstract

Abstract The design and synthesis of nitrogen‐doped aromatic belts with conjugated structures still remain a challenge. Here, we report the first nitrogen‐doped aromatic belt with a [6]cycloparaphenylene skeleton, which is conveniently synthesized from the easily available calix[3]carbazole. The aromatic belt has a rigid conjugated structure and deep cavity, and it can encapsulate one dichloromethane both in solution and in the solid state. Interestingly, the aromatic belt shows strong green fluorescence with a quantum yield of 0.39 and exhibits a narrow HOMO–LUMO energy gap of 2.02 eV. The belt‐shaped conjugated structure composed of three carbazole subunits has specific optoelectronic properties that will promote wide applications in supramolecular chemistry and materials science.

Topics & Concepts

Conjugated systemCarbazoleHOMO/LUMOFluorescenceSupramolecular chemistryChemistryAromaticityQuantum yieldNitrogenPhotochemistryDopingMaterials scienceOrganic chemistryCrystal structureMoleculePolymerOptoelectronicsPhysicsQuantum mechanicsSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsOrganic Electronics and Photovoltaics