Synthesis and Properties of Conjugated Nanohoops Incorporating Dibenzo[<i>a</i>,<i>e</i>]pentalenes: [2]DBP[12]CPPs

Abstract

Conjugated nanohoops allow studying the effect of cyclic conjugation and bending on the incorporated π-systems. To date, no such system containing antiaromatic units has been reported. We herein present [12]cycloparaphenylenes incorporating two dibenzo[a,e]pentalene units: [2]DBP[12]CPP nanohoops. Dibenzo[a,e]pentalene is a nonalternant hydrocarbon with antiaromatic character. The syntheses and optoelectronic properties of two different [2]DBP[12]CPP nanohoops with electronically modifying substituents are reported, accompanied by TDDFT calculations.