A high-yield, one-step synthesis of o-phenylene ethynylene cyclic trimer via precipitation-driven alkyne metathesis |
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| Authors: | Zhang Wei Brombosz Scott M Mendoza Jose L Moore Jeffrey S |
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| Institution: | Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA. |
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| Abstract: | reaction: see text] A shape-persistent, conjugated o-phenylene ethynylene cyclic trimer was prepared in one step from tetrasubstituted benzene monomer 4 in 86% isolated yield through precipitation-driven alkyne metathesis. The template-free, selective generation of the molecular triangle 5 is a thermodynamically favored process and under equilibrium control. A novel tetrameric macrocycle 7 was generated via scrambling metathesis between tricycle 5 and hexacycle 6 using this dynamic covalent chemistry. |
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