Luminescent Superbenzene with Diarylamino and Diarylboryl Groups

Dianisylamino donor and dimesitylboryl acceptor substituents were introduced at the 2,11-positions of hexa-peri-hexabonzocoronene (HBC) to demonstrate an,effective fluorescent enhancement of HBC as virtually nonfluorescent superbenzene. The present donor-acceptor substitution replaced the typical weak alpha-band with an intense intramolecular charge transfer band in the absorption spectrum) thereby leading to a much larger fluorescence quantum yield (Phi(f) = 0.56 in CH2Cl2) than any other HBC derivatives.