Developing ligands that can mimic a biological material in either its structure or function continues to be a highly active area of research. Cryptands have been investigated for their abilities in metal selectivity, increased binding stability, and as analogs to biological redox systems. Continued investigation into the N2S2, 1,8-dithia-4,11-diazacyclotetradecane has led us to investigate cryptand properties and the bridging effect on the macrocyclic ring. To understand the physical properties associated by incorporating the bridge, we synthesized varying lengths of the bridging carbon atoms (C3-C12). Cryptand bridging lengths C7 and C9 were synthesized in good yields and have fully characterized using 1H and 13C NMR in addition to COSY, HMBC and HMQC. X-ray analysis of C9 cryptamide has provided us with insight into the structural arrangement of the N2S2 ring. It is surmised that the cryptand ligands being developed will alter their redox properties through entropic modifications from the bridge length allowing variations in the metal redox potentials resulting in a tunable system.

Investigations into ligand tunability: Synthesis and characterization of NS containing cryptands

255th National Meeting (2018)

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