| Name | Mr. Cole Stearns |
|---|---|
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| Organization | University of Florida |
| Position | Graduate Student |
| Invited | No |
| Type | Oral |
| Topic | Organic Chemistry |
| Title | Structure-property relationships in heterofunctionalized [2.2]paracylophane supramolecular monomers |
| Author(s) | Cole D. Stearns, Ajeet Kumar, and Ronald K. Castellano |
| Author Location(s) | University of Florida |
| Abstract | [2.2]Paracyclophanes ([2.2]pCps) have been widely studied for decades due to their unique reactivity, optical properties and stereoelectronics, with many applications in donor-acceptor complexes, thin-film devices and organocatalysis. However, [2.2]pCps, unlike many other π-systems, have been virtually unexplored in a supramolecular context, and the first [2.2]Paracyclophane supramolecular polymers ([2.2]pCpSPs) were reported by our group in 2016. Experiments and computation have since shown that a strong macrodipole, solubility and amide connectivity can reliably dictate strong, cooperative supramolecular assemblies. In this work, we target these variables by synthesizing a library of tetrasubstituted hybrid-deck [2.2]pCps. These novel derivatives each have unique bis-(anilide) and bis-(carboxamide) functionalization and regiochemistry that significantly affect the assembly dipoles, interaction energies, and assembly strength of the resultant [2.2]pCpSPs. Solution studies, X-ray crystallography and density functional theory (DFT) are used to determine H-bonding geometry, elongation constant (Ke), assembly mechanism, SP macrodipole and many other parameters critical to optimizing this supramolecular scaffold. We are keen on applying our findings towards the realization of supramolecular block copolymers and chain-growth assemblies. |
| Date | 05/31/2024 |
| Time | 11:15 AM |
