|MIT Department: Chemistry
Faculty Mentor: Prof. Tim Swager
Undergraduate Institution: Case Western Reserve University
Website: LinkedIn, Twitter
My name is Cindy Serena Ngompe Massado (I go by Massado), and I am from Bafoussam, Cameroon. I am a rising senior at Case Western Reserve University majoring in Chemistry and minoring in Social Justice. Being someone who thrives on doing interdisciplinary work I value my current position as an undergraduate researcher in the Samia Lab doing nanomaterials research. My particular research interested lie in engineering nanomaterials and nanoparticle surfaces for various applications. My research goals are tied to and driven by my identity, and the issues I care about. My long-term goal, through earning a Ph.D. and going into academia as a researcher, is to build avenues of entry for those that have historically been excluded from or been ignored by these spaces. I feel that not only would this enrich the chemical discipline intellectually, it will make for a healthier, more welcoming research space.
Functionalized Carbon Nanotubes for Asymmetric Electrochemical Epoxidation
Cindy Serena Ngompe Massado1, Shao-Xiong Lennon Luo2 and
Timothy M. Swager2
1Department of Chemistry, Case Western Reserve University
2Department of Chemistry, Massachusetts Institute of Technology
Chiral epoxides serve as reagents for the synthesis of enantiomerically pure, biologically useful molecules. The synthesis of chiral epoxides is therefore crucial to the production of pharmaceutical compounds. The production of epoxides on a large scale often uses a heterogeneous system with peroxide-based oxidants such as hydrogen peroxide or alkyl peroxides which require extreme and toxic conditions. Homogeneous systems for obtaining enantio-enriched epoxides have involved asymmetric catalysis by metal complexes with chiral organic ligands. These have displayed great selectivity and yield but poor scalability. An ideal system would merge the benefits of these systems for more efficient large-scale synthesis. In this study, we present an electrochemical system utilising multi-walled carbon nanotubes (MWCNTs) functionalized with chiral ligands chelated to metal catalysts for the asymmetric epoxidation of olefins with water as an oxygen source. Here we show the optimization of synthesis conditions for the monooxazole and bisoxazole chiral ligand precursors. This was confirmed by NMR and MS results. These were then used for functionalization of MWCNTs. Functionalization by the bisoxazoline precursor was evaluated by XPS to yield 2.2 functional groups per 100 CNT carbons. By continuing this work, we aim to address the pitfalls of both heterogeneous and homogeneous systems. This system is expected to operate at room temperature and produce benign side products, making the system safer than the industry standard, while maintaining efficiency due to enhanced electrochemical electron transfer by the functionalized MWCNTs. These results would present new opportunities in enantioselective epoxidation and possibly dihydroxylation, as well as other asymmetric catalysis more broadly.