Organic luminescent radicals have been proposed to increase the efficiency of OLEDs and other electronic technologies. BDPA is a persistent organic radical that has been well known for decades and utilizes bulky fluorene groups to enhance stability of the radical. Our group is interested in synthesizing luminescent derivatives, particularly a compound we have named BAxPA, which replaces one of the fluorenes present in BDPA with azaxanthone. The main challenge in creating a molecule with the necessary steric bulk to prevent reactivity of a radical electron is maneuvering such bulky components to fit together. Our proposed strategy involves the use of phosphonate esters with reduced bulk in the Horner-Wadsworth-Emmons reaction to form the key chromophore-containing piece of our candidate radical BAxPA. I will outline my synthetic efforts toward making this key component of the radical and my experience with phosphorus-based chemistry.

Accessing tetrasubstituted alkenes en route to the organic radical BAxPA

ACS Spring 2022

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