Synthesis and photochromic properties of quinoxalino[e]-annelated dimethyldihydropyrene with planar chirality

9,10-Diacetyl-2,7-di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene annelated with a quinoxaline unit (q-DM-DHP, 3) was prepared from 5,13-di-tert-butyl-8,16-dimethyl[2.2]metacyclophane-1,2,9,10-tetraoxide (2) and o-phenylenediamine in two steps. The photochromic isomers of q-DM-DHP 3, closed form 3a and open form 3b, were separated by reverse-phase HPLC, and their isolated UV–visible spectra were estimated. The chiral HPLC analyses of q-DM-DHP 3 indicated their planar chirality, and their CD spectra were measured. The photochromic properties and thermodynamic properties of 3 were also discussed based on their UV–visible, 1H NMR, CD, and fluorescence spectra.