Document Type

Honors Project

Publication Date

6-2021

Abstract

We investigate the synthesis of allyl radical compounds, such as C. F. Koelsch’s free radical bis(diphenylene)-9’-phenylallyl (BDPA). BDPA is a persistent organic radical with magnetization properties. BDPA doesnot fluoresce, but we believe the substitution of a fluorene group with the chromophore 1-azaxanthone will induce luminescent properties and create a BDPA•derivative bis(diphenylene)-9’-azaxanthylene phenylallyl (BAxPA•). A convergent synthetic path was conducted in the development of BAxPA. The synthesis of 1-azaxanthone via a Friedel crafts reaction and a subsequent condensation produced the chromophore. The BDPA framework was created via varying Pudovik reactions that gave precursor molecules that will be used for the Horner-Wadsworth-Emmons reaction which combines azaxanthone with the BDPA framework. Several synthetic issues are explored in this investigation and a proposal for a new HWE route ensues. NMR and EPR spectroscopy are used to identify and characterize the compounds.

Level of Honors

magna cum laude

Department

Chemistry

Advisor

Graham Sazama

Available for download on Thursday, June 16, 2022

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