Professional Education

  • PhD, University of Florida, Chemistry (2021)
  • B.S., Florida Institute of Technology, Biochemistry (2016)

Stanford Advisors

All Publications

  • Tuning Supramolecular Polymer Assembly through Stereoelectronic Interactions. Journal of the American Chemical Society Henderson, W. R., Liu, G., Abboud, K. A., Castellano, R. K. 2021


    The supramolecular polymerization of 2,11-dithia[3.3]paracyclophanes through self-complementary intermolecular and transannular amide hydrogen bonding is presented. An n pi* interaction between the amide hydrogen bonding units and the central bridging atom results from the single-point exchange of a carbon atom for a sulfur atom. This orbital donor-acceptor interaction can be strengthened by oxidizing the sulfide to a sulfone which acts to shorten the donor···acceptor distance and increase orbital overlap. Experimental signatures of the increased n pi* interaction include larger isodesmic polymerization elongation constants in solution, changes in characteristic bond stretching frequencies, and geometric/structural changes evaluated by X-ray crystallography. The experimental data are supported by extensive computational investigations of both assembling and nonassembling 2,11-dithia[3.3]paracyclophanes as well as a rationally designed model system to confirm the role of stereoelectronic effects on supramolecular polymer assembly.

    View details for DOI 10.1021/jacs.1c05522

    View details for PubMedID 34346675