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
Recommended Citation
Vences, Kelly Xiomara, "In Pursuit of a Stable Luminescent Radical: Investigating an Olefin Synthesis via the Horner-Wadsworth-Emmons Reaction" (2021). Lawrence University Honors Projects. 165.
https://lux.lawrence.edu/luhp/165