With the aim of preparing a catalyst useful for di(cyanate ester) trimerization, a family of bis(aminoalkyl)norbornene ligands is under investigation.  There are many late transition metal complexes that can promote the cyclization of di(cyanate esters) to produce high-temperature thermosets useful in fiber reinforced composites.  However, the action of producing thermosetting materials dictates that the catalyst will be entrained in the thermoset for its lifetime.  There are concerns that over time, these residual catalytic species will degrade the material and thus limit its useful lifetime.  If a ligand can be designed to undergo a high-temperature, post-cure transformation to a molecule that will coordinatively saturate the metal catalyst, then it is likely that any entrained metal species will not have a long-term detrimental effect.  The work presented will focus on the design and synthesis of bis(aminoalkyl)norbornenes  that can chelate to a number of potential metal catalysts (<b>1</b>), and when thermally heated, undergo a retro-Diels-Alder reaction to a highly-reactive bis(aminoalkyl)cyclopentadiene (<b>2</b>).  This reactive cyclopentadiene is expected to combine with the metal and prevent any undesired long-term metal-assisted thermoset degradation chemistry.

Ligand design for permanent catalytic deactivation

2019 Fall National Meeting

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