Polymers are generally found in just about every aspect of daily life. Whether they be synthetic polymers or naturally-occurring polymers, many play important roles in material science. Self-healing polymers could unlock the door to a more efficient solution to repairing polymers. Thermal self-healing polymers are able to repair breaks in their chains by the application of heat from an external source. The Diels-Alder reaction is capable of producing the precursors of thermal self-healing polymer chemistry because the reaction is a single, concerted step that is also reversible at high temperatures. This study deals with the kinetics and thermodynamics of Diels-Alder reactions between several dienes and a single fluorinated dienophile, N-(4-fluorophenyl)maleimide. The dienes synthesized were 2-furylmethyl benzoate and 2-(methoxymethyl)furan. These dienes were produced to determine how substituent groups affect the relative rates in these Diels-Alder reactions. These reactions were also subjected to thermodynamic studies at varying temperatures and were monitored using 1H & 19F NMR spectroscopy. The data collected from both the kinetic and thermodynamic studies of these two dienes will be discussed.

Kinetic & thermodynamic studies of 2-furylmethyl benzoate and 2-(methoxymethyl)furan in model Diels-Alder reactions

255th National Meeting (2018)

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