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Abstract
We developed a fully abiotic approach to template the synthesis of discrete unimolecular polyolefins. Discrete, unimolecular oligo(thiophene)s with alternating sequence were obtained by iterative convergent/divergent couplings and then functionalized with pendant cyclic olefin monomers in the side chains. Upon treatment with the Grubbs third-generation catalyst in dilute solution (0.15 mM in DCM at 0 °C), the pendant monomers undergo templated ring-opening metathesis (TROM). Then, the daughter olefin is liberated from the parent thiophene by hydrolysis. Cyclooctenes undergo TROM to afford macrocyclic products that exactly replicate the chain length of the parent oligomer, as evidenced by MALDI MS/MS and NMR. Norbornene derivatives also undergo TROM and replicate unimolecular chain lengths, but in contrast, they exclusively form the linear oligomeric products with styrenic end groups. A template that was functionalized with one norbornene unit at the α chain end, followed by five cyclooctene units along th...
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