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Updated: Jul 13, 2026

Microwave-assisted Functionalization of Poly(ethylene glycol) and On-resin Peptides for Use in Chain Polymerizations and Hydrogel Formation
Published on: October 29, 2013
Efficient, high-yield route to long, functionalized p-phenylene oligomers containing perfluorinated segments, and
1Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley 94720, USA.
Abstract:
Linear oligophenylene diynes containing 6, 9, and 12 phenylene rings were synthesized in high yields using the nucleophilic aromatic substitution (S(N)Ar) of perfluoroarenes by aryllithium reagents as the key carbon-carbon bond-forming reaction. This reaction was demonstrated to proceed readily at low temperatures with sterically hindered substrates and in the presence of base-sensitive silylalkynyl groups. Diynes synthesized by this methodology were readily zirconocene-coupled into large dimeric macrocycles using the zirconocene reagent Cp(2)Zr(py)(Me(3)SiC triple bond CSiMe(3)).
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