The polymerization of phenylacetylene with the L-lysine was performed in THF using Rh(nbd)BPh4 as a catalyst ([1]/[Rh(nbd)BPh4] = 50, [1] = 0.030 mol L-1) to afford the corresponding poly(phenylacetylene) derivative (poly-1). The number average molecular weight (Mn) and polydispersity (Mw/Mn) of poly-1 were determined to be 2.5 � 105 and 3.4, respectively. A different color change in poly-1 solution with respect to tetra-n-butylammonium L-leucine (TBA-L-Leu) and D-leucine (TBA-D-Leu) was observed and further supported by the UV-vis measurements. In the CD spectra, the first Cotton effect was observed in the absorption domain of the main chain of TBA-L-Leu, but not in the case of TBA-D-Leu. These results suggested that poly-1 possessed chiral responsiveness, which find important applications particularly as chiral sensors.

Chirality sensing towards amino acid using poly(phenylacetylene) conjugated with l-lysine through urea linkage

241st National Meeting (2011)

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