Vinyl monomers bearing chromophore moieties and their polymers. II. Fluorescence and initiation behavior of N-(4-N′, N′-dimethylaminophenyl)maleimide and its polymer

✍ Scribed by Hui Cai; Xiao-Hui He; Dong-Ying Zheng; Jian Qiu; Zi-Chen Li; Fu-Mian Li

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 489 KB
• Volume: 34
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(199605)34:7<1245::aid-pola11>3.0.co;2-9

✦ Synopsis

A maleimide bearing electron-donating chromophore, N-(4-N,N-dimethylaminophenyI)maleimide (DMAPMI) was synthesized from N,N-dimethylaminoaniline and maleic anhydride in the presence of acetic anhydride and sodium acetate. DMAPMI can be easily copolymerized with vinyl acetate (VAc). In addition, it can be easily homopolymerized by UV light irradiation or by using AIBN or BPO as a n initiator. The fluorescence spectra of DMAPMI and its polymer or copolymer were recorded and compared at the same chromophore concentrations. It was observed that the fluorescence emission intensity of DMAPMI was much lower than those of its polymers. This may be due to the occurrence of intermolecular charge transfer interaction between the electron-donating dimethylaminophenyl moiety and acrylic electron-accepting carbon-carbon double bond in the monomer. The model compound, N-(4-N,N-dimethylaminophenyl)succinimide (DMAPSI), which has no carbon-carbon double bond, displayed the same fluorescence behavior as DMAPMI polymers. The fluorescence of DMAPMI polymers and DMAPSI can be quenched by electron-deficient compounds such as AN, TCNE, MMA, etc. All these results supported the above conclusion. This is another example of the "fluorescence structural self-quenching effect" termed by us previously and demonstrates again that this phenomenon is not an accidental but a general one for acrylic monomers bearing electron-donating chromophores. Study of the initiation behavior of DMAPMI and its polymer showed that they could initiate the photopolymerization of AN, by combination with BPO, they could also initiate the thermopolymerization of vinyl monomers such as MMA. 0