College of Science and Health Theses and Dissertations

Date of Award

Winter 3-20-2020

Degree Type




First Advisor

Kyle Grice, PhD

Second Advisor

Ruben Perez, PhD


Novel trisubstituted ethylenes (TSE), chloro and fluoro 2-cyano-3-phenyl-2-propenoic propenoates (XPhCH=C(CN)CO2CH(CH3)2) were prepared and copolymerized with styrene (ST). The monomers were synthesized by modified crossed aldol condensation reaction (Knoevenagel condensation) of chloro and fluoro ring-substituted benzaldehydes with isopropyl cyanoacetate using piperidine as catalyst. They were subsequently characterized by IR, 1H and 13C-NMR and CHN analysis as well. The novel TSE monomers formed were then copolymerized with styrene (ST) in solution at 70 °C and 1,1′-Azobis(cyclohexanecarbonitrile) (ABCN) was used as radical initiator of the reaction. The composition of the novel copolymers was calculated from nitrogen analysis and their structures were analyzed by IR, 1H and 13C-NMR. The order of relative reactivity (1/r1) for the TSE monomers was calculated to be: 2,3,5,6-tetrafluoro (1.30) > 2,3,6-trichloro (1.21) > 2,3,4-trifluoro (1.20) > 3,4,5-trifluoro (1.17) > 2,3,4,5,6-pentafluoro (1.16) > 2,4,5-trifluoro (0.99) > 2,4,6-trifluoro (0.81). Thermogravimetric analysis (TGA) showed that decomposition of the synthesized copolymers in nitrogen occurred in two steps.

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