Circularly polarized peroxyoxalate chemiluminescence with chiral activators

Abstract

A series of planar chiral macrocyclic compounds derived from [2.2]-paracyclophane scaffold and helicenes in enantiomers were synthesized and found to be efficient circularly polarized emitters. These chiral macrocyclic compounds and helicenes were used as activators in peroxyoxalate chemiluminescence. Among the blue, green, or yellow chemiluminescent activators, compound 2R containing electron-donating dimethylamino groups with lowest oxidation potential showed the best chemiluminescence quantum yield of 0.21% (higher than 0.17% of 9,10-diphenylanthracene at the concentration of 1.0 × 10−4 mol dm−3). Appreciable circularly polarized chemiluminescence with dissymmetry factors (|gCL|) in the range of 1.4 × 10−3−5.4 × 10−3 have been recorded for these chiral chemiluminescent activators.