Live Poster Session: Zoom Link
Thursday, July 30th 1:15-2:30pm EDT
Abstract: Dendrimers, a type of highly branched macromolecule, play a key role in drug delivery, tissue engineering and the design of specialty polymers. Diels-Alder and thiol-maleimide click chemistry reactions using furan maleimide have been previously studied as a means of synthesizing multilayered dendrimers, however, the maleimide derivatives were found to be poorly soluble in dendrimers of three generations or greater. Because insolubility limits dendrimer growth, it is beneficial to investigate alternative derivatives that might lead to more soluble dendrimers. Vinyl sulfone derivatives, an alternative to maleimide thought to be more soluble but still able to undergo reversible Diels-Alder reactions, were computationally investigated. In the Diels-Alder reactions studied, the energetics of a methyl vinyl sulfone dienophile reacting with different cyclic dienes such as furan, cyclopentadiene, thiophene and dimethyl fulvene were investigated. The changes in enthalpy and free energy for both the overall reactions and transition states were calculated using ab initio computations which were performed at the B3LYP/6-31G(d), M062x/6-311G(2d,p), wB97xd/6-311G(2d,p) and CBS-QB3 levels of theory using the program Gaussian16. The values generated indicate that the furan-methyl vinyl sulfone reaction is likely to be a reversible Diels-Alder reaction similar to that of furan-maleimide, though with a somewhat higher energetic barrier and smaller thermodynamic driving force.
Final-Summer-Research-2020Live Poster Session: Zoom Link
Thursday, July 30th 1:15-2:30pm EDT