The mechanochemical response of an anthracene and maleimide Diels-Alder adduct (1) was investigated for the purpose of demonstrating small molecule release and unveiling masked fluorescence under applied force.  The synthesis of 1 began with the reaction of 2,6-bis(hydroxymethyl) anthracene and n-ethylmaleimide through the Diels-Alder reaction.  Polymer handles were necessary for the transduction of force under pulsed ultrasound, so a difunctional initiator was synthesized from 1 via esterification of hydroxyl groups to create 2-bromoisobutyrate esters and polymer chains were grown with ATRP.   GPC-UV analysis after pulsed ultrasound indicated polymer chain scission, but did not reveal an increase in UV absorbance at 365 nm as expected.

Probing Diels-Alder adducts of anthracene and maleimide as mechanically active functional groups

245th National Meeting (2013)

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