b'Preparation of the Polyoxotungstate,[n-(C 4 H 9 ) 4 N] 3 [a-PW 12 O 39 (NC 6 H 4 -CC-SI(CH 3 ) 3 )], by Sonogashira Coupling of Trimethylsilylacetylene with a- [PW 12 O 39 (NC 6 H 4 -I)] 3-Kahleel Guerrier, Thomas Mancil, Nathan Hart, and Alana HiersSponsor: Dr. DuncanThe functionalization of redox-active metal-oxide molecules with organic groups is a promising research direction for creating new functional materials wherein the organic components serve two principal functions: (1) they enable tuning of the metal-oxide redox potentials and extend their light absorption into the visible region; and (2) they enable the spatial organization and concomitant tuning of electronic couplings between metal-oxide molecules that are the principal functional units in supramolecular metal-oxide assemblies. Such functionalization permits the development of tunable redox/photoredox catalysts in artificial photosynthetic schemes and other complex multistep catalytic reactions, the construction of electronic devices operating at the nanometer length scale, and more generally, controlling the emergence of cooperative properties in metal-oxide materials. Using a synthetic protocol developed in our laboratory, we are able to functionalize metal oxide molecular anions, e.g. [PW12O40]3-, by formal replacement of surface oxide, O2-, with the isocharged arylimido group, C6H5N2-. In the research presented here, we show that the p-iodoarylimido derivative,a -[PW12O39(NC6H4-I]3-, is amenable to further modification by attaching additional organic groups to the aryl ring via Sonogashira carbon-carbon bond coupling reactions. We also report an important advancement in this chemistry, namely that creating three-dimensional bulk on the aryl ring enables separation of the persistent impurity, a -[PW12O40]3-, from the target compound by simple recrystallization. This is demonstrated for the tetra-n-butylammonium salt ofa -[PW12O39(NC6H4-CC-Si(CH3)3)]3-. Prior to this development, purification required cation metathesis followed by reversed phase chromatography, which proved to be tedious and difficult for these compounds. We report here progress on making and purifying multigram quantities ofa -[PW12O39(NC6H4-CC-Si(CH3)3)]3- isolated as a tetra-n-butylammonium salt along with efforts to obtain crystals suitable for single crystal X-ray diffraction analysis.Deep Eutectic Solvents as Green and Efficient Solvents for the Extraction of CarotenoidsJwalant Bijal ShahSponsors: Dr. Sreenilayam and Dr. FocsanThe extraction of bioactive compounds from natural products using conventional organic solvents can leave large traces of organic solvents behind. This can lead to pollution in the environment and can also leave traces of the organic solvents in the extracts. Even after having such an impact on the environment the extraction yields obtained are fairly low. It is important to find an alternative method of extraction that can solve these problems. Deep eutectic solvents (DESs) can be used as an alternative as they are considered more environmentally friendly, have low toxicity, low cost, and can give better extraction yields. In this study, a wide range of DESs will be synthesized for the extraction of B-carotene and Lycopene from tomato paste and paprika. The experimental approach will include sonication baths, vortexing, and centrifugation to obtain a proper mixture. The mixture will then be analyzed under a UV spectrophotometer and an HPLC. It is expected that using a DES solvent instead of a conventional organic solvent will reduce toxicity and increase extraction yield because of the nonpolar properties of DES solvents. Sufficient data from this study can induce a change that can make extractions environmentally friendly.22'