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

Two vinyloxy monomers bearing electron-accepting naphthalimide with different spacer lengths, i.e.N-(2-vinyloxyethyl)-1,8-naphthalimide (VOENI) and N-(6-vinyloxyethyl)-1,8-napholimide (VOHNI) were synthesized by the reaction of potassium 1,8-naphthalimide with corresponding omega -chloroalkyl vinyl ethers. These monomers can be polymerized cationically, and copolymerized radically with N-actoxyethylmaleimide (AEMI). The fluorescence behaviors of the two monomers were studied by comparing with that of their saturated model compound in order to further understand the nature of fluorescence structural self-quenching effect (SSQE). It was found that the SSQE of these monomers depends on the spacer lengths between the naphthalimide moiety and the vinyloxy group, as well as the properties of solvents used. It is demonstrated that the SSQE of these monomers occurs mainly via the intramolecular charge transfer interaction between the electron-donating vinyloxy group and the electron-accepting 1,8-naphthalimide chromophore upon UV irradiation. In addition, the fluorescence behavior of the copolymer of VOENI and AEMI was also studied. Copyright (C) 2000 John Wiley & Sons, Ltd.Polymer ScienceSCI(E)EI2ARTICLE8-12798-8041