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Designing New Macromolecular Architectures

Over the past twenty-five years, the feasibility of synthesizing 3D cages and (more recently) COFs with large-volume cavities via multitopic Dynamic Covalent Chemistry has been demonstrated. To date, DCC has utilized imine, boronic ester condensation, disulfide exchange reactions and alkene metathesis. Although feasibility has been demonstrated, it remains a challenge to predict the outcome of a multitopic precursor subjected to DCC. We (and others) surmised that a simpler connecting geometry would alleviate this problem. Toward this end, alkyne metathesis (AM) has emerged as an attractive addition to the DCC toolbox. AM exchanges carbon-carbon triple bonds – a connecting group with a simple, linear geometry that has no directionality. However, even with these simplifications, product prediction remains a challenge with AM. Our project aims to better understand how to more reliably use AM in DCC.
kinetically viable pathways for mutlitopic dynamic covalent chemistry via alkyne metathesis border=


Representative Publications

  1. Moneypenny, T.P.; Walter, N.P.; Cai, Z.; Miao, Y.-R.; Gray, D.L.; Hinman, J.J.; Lee, S.; Zhang, Y. and Moore, J.S. Impact of Shape Persistence on the Porosity of Molecular Cages. J. Am. Chem. Soc. 2017, 139, 3259-3264. DOI: 10.1021/jacs.7b00189
  2. Lee, S.; Chenard, E.; Gray, D.L.; Moore, J.S. Synthesis of Cycloparaphenyleneacetylene via Alkyne Metathesis: C70 Complexation and Copper-Free Triple Click Reaction, J. Am. Chem. Soc., 2016, 138, 13814-13817.DOI: 10.1021/jacs.6b08752
  3. Lee, S.; Yang, A., Moneypenny II, T.; Moore, J.S. "Kinetically Trapped Tetrahedral Cages via Alkyne Metathesis", J. Am. Chem. Soc., 2016, 138, pp 2182–2185. DOI:10.1021/jacs.6b00468
  4. Gross, D.E.; Moore, J.S. "Arylene-Ethynylene Macrocycles via Depolymerization-Macrocyclization" Macromolecules 2011, 44, 3685-3687. DOI: 10.1021/ma2006552
  5. Sisco, S.W.; Moore, J.S. "Directional Cyclooligomers via Alkyne Metathesis" J. Am. Chem. Soc. 2012, 134, 9114-9117. DOI:10.1021/ja303572k
  6. Finke, A.D.; Gross, D.E.; Han, A.; Moore, J.S. "Engineering Solid-State Morphologies in Carbazole–Ethynylene Macrocycles", J.Am.Chem. Soc. 2011, 133, 14063-14070. DOI: 10.1021/ja204795q
  7. Elliott, E.L.; Hartley, S.; Moore, J.S. "Covalent Ladder Formation Becomes Kinetically Trapped Beyond Four Rungs" Chem. Comm. 2011, 47, 5028-5030. DOI: 10.1039/C1CC11242B