We prepared a new overcrowded tristricyclic aromatic ene (TAE) and investigated its external stimuliresponsive behavior for the switching between a closed-shell folded form and an open-shell twisted form. Upon photoirradiation, the folded form transforms into the biradical twisted form, whereas by keeping the twisted form in the dark, the reverse reaction gradually occurs at room temperature. This switchable conformational change is analyzed by means of UV−vis and electron spin resonance spectroscopies, cyclic voltammetry, density functional theory calculations, and kinetic studies. Article pubs.acs.org/joc
Anthracene-attached tricyclic aromatic hydrocarbon radicals having different central polygons, Ant-5, Ant-6, and Ant-7,w ere synthesized to evaluatet he role of an anthracene substituent group in the stabilitya nd reactivity of tricyclic aromatich ydrocarbon radicals. The bulky anthryl group effectively protects ac arbon atom with high spin density,r esultingi nh igh persistence of the radicals. On the other hand, the combination of the anthrylg roup and the tricyclica romatic scaffold makes the molecular structure drastically change from at wisted form to af olded form and an unpaired electron movesi nto the anthryl moiety,e ventually affordingatail-to-tail s-dimer.[a] Dr.
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