Vinyl monomers bearing chromophore moieties and their polymers. VIII. synthesis and fluorescence behavior of a vinyloxy monomer having an electron-accepting chromophore moiety,p-((vinyloxy)methyl)benzonitrile, and its polymers

Du, Fu‐Sheng; Li, Zi‐Chen; Li, Fu‐Mian

doi:10.1002/(sici)1099-0518(19990115)37:2<179::aid-pola8>3.0.co;2-4

Cited by 7 publications

(1 citation statement)

References 15 publications

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“…These monomers could be photopolymerized and acted as sensitizers to initiate the photopolymerizations of other electron‐deficient monomers, such as methyl methacrylate (MMA) and acrylonitrile (AN), through a photoinduced charge‐transfer intermediate. However, for vinyl monomers with an opposite state in their electronic structure as compared to the aforementioned acrylic monomers, SSQE also has been observed 6, 7. This means that SSQE is not an accidental phenomenon but commonly is observed in monomers whose carbon–carbon double bonds and fluorescent chromophore moieties are opposite in their electronic properties.…”

Section: Introductionmentioning

confidence: 99%

Vinyl monomers bearing chromophore moieties and their polymers. XI. Synthesis and photochemical behavior of carbazole‐containing methacrylic monomers and their polymers

Hong

et al. 2000

J. Polym. Sci. A Polym. Chem.

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Three carbazole‐containing methacrylic monomers, 2‐(N‐carbazolyl)ethyl methacrylate(CzEMA), 6‐(N‐carbazolyl)hexyl methacrylate(CzHMA), and 11‐(N‐carbazolyl)undecyl methacrylate (CzUMA), and their saturated model compounds, 2‐(N‐carbazolyl)ethyl isobutyrate, 6‐(N‐carbazolyl)hexyl isobutyrate, and 11‐(N‐carbazolyl)undecyl isobutyrate, were synthesized and polymerized. UV absorption spectra showed that there was either negligible or no interaction between the carbon–carbon double bond of the methacrylic group and the carbazolyl chromophore moiety in the ground state for these monomers. Fluorescence spectra of the monomers, their model compounds, and the polymers were recorded in the solvents with different polarities. CzEMA exhibited the fluorescence structural self‐quenching effect (SSQE), but CzHMA and CzUMA did not. In addition, the SSQE of CzEMA depended strongly on the polarity of the solvents. That is, the stronger the polarity of a solvent was, the more obvious the SSQE was. Therefore, the SSQE of CzEMA mainly was caused by the intramolecular charge‐transfer interaction between the excited electron‐donating carbazolyl chromophore moiety and the electron‐accepting carbon–carbon double bond of the methacrylic group. This was confirmed by the fluorescence‐decay curves and the fluorescence lifetimes of the monomers, their model compounds, and the polymers. The monomers, their model compounds, and the polymers initiated the photopolymerization of methyl methacrylate (MMA) upon UV irradiation. CzEMA showed greater initiation ability than the other two monomers and their model compounds; this was ascribed to the photoinduced intramolecular charge‐transfer interaction. The higher initiation efficiency of the homopolymers compared to that of the copolymers with MMA was interpreted as the result of singlet energy migration of the excited carbazolyl chromophores along the polymer chains. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 679–688, 2000

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Section: Introductionmentioning

confidence: 99%

Vinyl monomers bearing chromophore moieties and their polymers. XI. Synthesis and photochemical behavior of carbazole‐containing methacrylic monomers and their polymers

Hong

et al. 2000

J. Polym. Sci. A Polym. Chem.

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Vinyl monomers bearing chromophore moieties and their polymers. XII. Synthesis and fluorescence behavior of vinyloxy monomers having 1,8-naphthalimide moiety with different spacer lengths and their polymers

Zhou

et al. 2000

Polym. Adv. Technol.

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Mono‐, bis‐, and trismaleimides having electron‐donating chromophores: Fluorescence, electrochemical properties, polymerization, and cure monitoring

Zhang

Wang

et al. 2005

J. Polym. Sci. A Polym. Chem.

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Mono‐, bis‐, and trismaleimides (MM‐2, BM‐4, and TM‐6, respectively) bearing electron‐donating chromophores generally displayed strong fluorescence quenching. The quenching mechanism of fluorescence was revealed by electrochemical studies. On the basis of the electrochemical data, an energy level diagram was established for these maleimides. The electron‐donating ability increased in the order of TM‐6 < BM‐4 < MM‐2. The electron‐accepting ability increased in the opposite order, that is, from MM‐2 to BM‐4 to TM‐6. The copolymerization of multimaleimides with diamine could be well monitored by fluorescence spectroscopy. Compared with fluorescence probe techniques, the fluorescence monitoring could directly reflect the consumption of CC bonds. Furthermore, a novel trismaleimide resin was preliminarily studied, in which TM‐6 was a dual‐purpose functional monomer acting not only as a crosslinker but also as an intrinsic fluorophore to monitor its crosslinking or cure process. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 304–313, 2006

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Vinyl monomers bearing chromophore moieties and their polymers. VIII. synthesis and fluorescence behavior of a vinyloxy monomer having an electron-accepting chromophore moiety,p-((vinyloxy)methyl)benzonitrile, and its polymers

Cited by 7 publications

References 15 publications

Vinyl monomers bearing chromophore moieties and their polymers. XI. Synthesis and photochemical behavior of carbazole‐containing methacrylic monomers and their polymers

Vinyl monomers bearing chromophore moieties and their polymers. XI. Synthesis and photochemical behavior of carbazole‐containing methacrylic monomers and their polymers

Vinyl monomers bearing chromophore moieties and their polymers. XII. Synthesis and fluorescence behavior of vinyloxy monomers having 1,8-naphthalimide moiety with different spacer lengths and their polymers

Mono‐, bis‐, and trismaleimides having electron‐donating chromophores: Fluorescence, electrochemical properties, polymerization, and cure monitoring

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