Bismaleimides and bisitaconimides bearing diphenylmethylamine, triphenylamine, or 2,5-diphenyl-1,3,4-oxadiazole chromophore (symbolized as A(=)−D
(*)
−A(=)), as well as their saturated model
compounds were synthesized, and their steady-state and time-resolved fluorescence spectra were
investigated. These A(=)−D(*)−A(=) monomers display strong intramolecular fluorescence quenching. Their
fluorescence quantum yields and lifetimes are generally lower than those of their model compounds. It
was found that the electron-poor CC bond of maleimide and itaconimide units (A(=)) plays a key role in
the intramolecular quenching, which is correlated to the electron-accepting ability of A(=) and the geometry
arrangement between A(=) and electron-donating chromophore (D(*)). The intramolecular quenching was
attributed to an intramolecular charge transfer interaction, which was confirmed by intermolecular
fluorescence quenching and time-resolved fluorescence studies. On the basis of the intramolecular
quenching, a new fluorescence approach can be developed to monitor the process of the polymerization
and curing of bismaleimides, which can directly reflect the CC bond consumption during polymerization
and curing. The new fluorescence approach can be utilized not only by an intrinsic fluorescence technique
but also by an extrinsic fluorescence technique.