Unveiling a Quinoidal 2,3:10,11-Dibenzoheptazethrene

Parent 2,3:10,11-dibenzoheptazethrene is a singlet diradicaloid polycyclic hydrocarbon in the ground state that did not change its diradical character upon substitution (methyl and triisopropylsilylethynyl). Described herein are the synthesis andcharacterization of an ethoxy/3,5-(CF3)2C6H3-substituted 2,3:10,11-dibenzoheptazethrene3that prefers to retain itsp-quinoidalcore and shows zero diradical character, as determined by single-crystal analysis and density functional theory calculations. Negativesolvatochromism,pi-pi interactions, Csp2-HmiddotmiddotmiddotO hydrogen bonding, intramolecular charge transfer, redox amphotericity, and anarrow HOMO-LUMO energy gap make3a potential candidate for application in optoelectronics

Automated summary

This article describes the synthesis and characterization of a 2,3:10,11-dibenzoheptazethrene material with ethoxy / 3,5-(trifluoromethyl) 2C6H3 substitution. The material retains its p-quinoidal core and lacks diradical character, as confirmed by single-crystal analysis and density functional theory calculations. It exhibits negative solvatochromism, π-π interactions, hydrogen bonding, charge transfer, redox amphotericity, and a narrow energy gap, making it a potential candidate for optoelectronic applications.