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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 Chemie International Edition72 citationsDOI

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 chemistryNitrogenAromaticityPhotochemistryQuantum yieldChemistryDopingMaterials scienceOrganic chemistryCrystal structurePolymerMoleculeOptoelectronicsPhysicsQuantum mechanicsSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsOrganic Electronics and Photovoltaics
A Green Fluorescent Nitrogen‐Doped Aromatic Belt Containing a [6]Cycloparaphenylene Skeleton | Litcius