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Tuning The Kinetics And Energetics Of Diels−Alder Cycloaddition Reactions To Improve Poling Efficiency And Thermal Stability Of High-Temperature Cross-Linked Electro-Optic Polymers

Z. Shi, W. Liang, J. Luo, Su Huang, B. Polishak, Xiaosong Li, T. R. Younkin, B. Block, A. Jen
Published 2010 · Materials Science

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A comprehensive theoretical and experimental study of the bromo effect on Diels−Alder (DA) and retro-Diels−Alder (rDA) reactions between the anthracene-containing dienes and maleimide dienophile has been conducted to improve thermal stability and poling efficiency of electro-optic (EO) polymers. Calculations with density functional theory (DFT) reveal that the bromo substitution on anthracene-based dienes leads to significantly increased cycloaddition exothermicities (9−12 kcal/mol) but has a minor effect on their activation barriers (0.6−3 kcal/mol) when reacted with N-phenylmaleimide dienophile. These calculated values correlate very well with the experimental results obtained from a series of model compounds. The DA/rDA cross-linking protocols based on these compounds can be applied to several nonlinear optical (NLO) polymers and result in large EO coefficients (r33) (as high as 69 pm/V) and greatly improved thermal stability (up to 250 °C). This demonstrates that controlled DA/rDA reactions can be use...

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