Bismaleimides bearing electron-donating chromophore moieties, A (=)-D (*)-A (=) type monomers, i.e. N,N-bis(4-maleimidophenyl)methylamine (BMIPMA), N,N-bis(4-maleimidophenyl)aniline(BMIPA) and 2,5-bis(4-maleimido phenyl)-1,3,4-oxadiazole(BMIPODA) as well as their corresponding saturated model compounds, i.e. N,N-bis(4-succinimidophenyl)methylamine( BSIPMA), N,N-bis(4-succinimidophenyl)aniline(BSIPA) and 2,5-bis(4-succimidophenyl)-1,3,4-oxadiazole (BSIPODA) were synthesized. It was found that the fluorescence quantum yields of A (=)-D (*)-A (=) monomers were always dramatically lower than those of their corresponding saturated model compounds. These A (=)-D (*)-A (=) bismaleimides possess a strong SSQE, which is attributed to an intramolecular charge transfer interaction.
A β-diketone-bridged chromophore-containing acrylic monomer, 1-(4-dimethylaminophenyl)-4-methyl-4-pentene-1,3-diketone(DMPDK) and its saturated model compound, 1-(4-dimethyl aminophenyl)-1,3-butanedione(DMBDK) were synthesized and investigated by spectroscopy. It was found that the fluorescence intensity of DMPDK was much lower than that of DMBDK at the same concentration, which indicates that DMPDK, a β-diketone-bridged acrylic monomer having chromophore moiety, also showed fluorescence structural self-quenching effect(SSQE). Photo-induced tautomerization of DMBDK in acetonitrile was studied by means of UV and fluorescence spectroscopy. The results imply that the fluorescence method is capable of monitoring tautomerization of some fluorescent β-diketones.
