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A novel type of mono-substituted polyacetylene: Synthesis and characterization of poly(N-propargylthiourea)s

Designed Monomers and Polymers, ISSN: 1385-772X, Vol: 14, Issue: 2, Page: 143-154
2011
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This article reports for the first time about a novel category of mono-substituted acetylene monomers (1-4, M1-M4) (C≡CCH NHCSNHR, R for M1 = CHCH; M2 = (CH )CH; M3 = (CH) CH; M4 = CH). The four monomers were identified by FT-IR, H-NMR, C-NMR spectroscopy and elementary analysis. In the presence of a rhodium catalyst ((nbd)Rh B(CH) (nbd = 2,5-norbornadiene)), M1-M4 underwent polymerization and provided the expected poly(N-propargylthiourea)s in a moderate to high yield (58-92%) and with a high cis content (≥91%) in the polymer backbones. The substituents had a big influence on the solubility of poly(N-propargylthioureas). Among the four polymers, polymer 4 (poly(4)) showed good solubility and relatively higher number-average molecular weight (up to 12 000). This polymer was further characterized by FT-IR and UV-Vis spectroscopy. TGA analysis demonstrated that the polymer remained stable up to 175° C. Poly(4) exhibited considerable adsorption ability toward to Fe ions. The novel substituted polyacetylenes are also expected to exhibit some unique properties, such as inhibition of bacteria, chiral recognition, metal extraction and metal detection, derived from a combination of conjugated polymer backbones and highly functional thiourea groups in the side-chains. © 2010 Koninklijke Brill NV, Leiden.

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