Stereochemical evidence for participation of a Donor-acceptor complex in alternating copolymerization. 1. Model compound synthesis

Abstract

The stereospecific synthesis of a series of model compounds for N-substituted maleimide/vinyl ether alternating copolymers is described. The stereochemistry of the compounds prepared could be unambiguously deduced via utilization of 1H NMR coupling constants. Comparison of the 13C NMR chemical shifts of the model compounds with those of the copolymers suggests that the predominant stereochemistry at the succinimide units in the copolymers is erythro. A detailed comparison of the several properties of the copolymers with those of the model compounds is reported in an accompanying paper.

Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization

“…It has been suggested that, if an EDA complex participate in a copolymerization, some structural evidences related to the structure of the complex may be found in the copolymer [24,28,29,31]. It has been also suggested [32] that the relative amounts of the cis and trans linkage configurations at the succinimide rings in the copolymers are closely related to the quantitative role of the EDA complex in alternating copolymerization.…”

Light-induced crosslinking polymerization of a novel N-substituted bis-maleimide monomer

“…The photoinduced polymerization of electron donor/-electron acceptor monomer systems has been extensively studied in the past few years, mainly the vinyl ether/maleimide combination, as such non-acrylate UV-curable resins have the distinct advantage of undergoing a rapid polymerization upon UV exposure in the absence of any added photoinitiator [1][2][3][4][5][6][7][8][9]. Some N-substituted maleimide monomers have been shown to undergo homopolymerization even when they are exposed neat to UV-radiation, provided that the monomer contains easily abstractable hydrogens [8].…”

Polymers Based on Phenols

“…The free-radical chain polymerization of maleimides and the N-substituted derivatives has been extensively studied 156,159,160,175,176,184 and both homo-and copolymerization reactions occur readily with a variety of N-substituents and comonomers 142,143,152 . Their reactivity is a consequence of the electron-withdrawing nature of the two adjacent carbonyl groups, which creates a very electron-deficient double bond.…”