Dynamic covalent chemistry (DCC) is a synthetic strategy to make use of reversible formation and breaking of covalent bonds to produce complex supramolecules. As dynamic covalent components, disulfides have been shown to be effective partners in the self-assembly of supramolecular systems. In this poster, we aim to advance our fundamental understanding of pnictogen-assisted iodine oxidation of thiols to disulfides by exclusively focusing on a DCC approach, where varying degrees of social sorting can be exploited to create functional assemblies. We will show that the distribution of the disulfide products derived from the previously unreported bis(mercaptomethyl) biphenyl system can be easily tuned by changing ligand concentration and equivalents of the iodine oxidant. We will also demonstrate that social self-sorting is favored in the “mixed” DCC system than the more commonly observed narcissistic self-sorting in related systems in the literature. By carefully choosing two ligands of similar shapes and coordination motifs but different sizes, we will report the isolation of novel and traditionally elusive “heteroleptic” trimers, which open new directions into the synthesis of lower symmetry cyclophanes, a field traditionally dominated by more symmetric, “homoleptic” structures.

Self-sorting behavior in two dynamic covalent chemistry systems generated from pnictogen-assisted iodine oxidation

2019 Spring National Meeting

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