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
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.
Available for download on Thursday, June 16, 2022