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

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.

Highly efficient charge transport across carbon nanobelts

“…The [6]CNB_M6 and [6]CNB_N3 containing the pentagon ring represent the segment structures of unconventional Haeckelite CNTs and are synthesized according to previously reported procedures (fig. S1) (14,15). All molecules are dissolved into 1-chloronaphthalene solvent with a concentration of ~0.1 mM for the STM-BJ measurement in ambient conditions and room temperature.…”

“…The first armchair CNB consisting of solely fused benzene rings was first synthesized in 2017 and extended in 2018 (9,10), and later, two types of all-benzene CNBs with chiral and zigzag structures have been reported (11)(12)(13). Recently, the family of CNBs is further expanded by the synthesis of new forms of CNBs containing nonhexagonal rings (14)(15)(16)(17)(18), heteroatom dopants (15,17,(19)(20)(21)(22), and complex topologies (23,24). These breakthroughs inspire intensive experimental and theoretical explorations of fundamental physical properties associated with the unique belt-shaped structures of CNBs (25)(26)(27)(28).…”