Macromolecules, Vol.42, No.13, 4430-4435, 2009
Effect of the Pendant Structure on Anion Signaling Property of Poly(phenylacetylene)s Conjugated to alpha-Amino Acids through Urea Groups
A colorimetric detection of guest counteranions has been demonstrated using poly(phenylacetylenes)s with urea functionalities and alpha-amino acids, such as L-leucinie, L-glutamic acid, L-aspartic acid, L-phenylalanine, L-isoleucine, and L-alanine (PPA-Leu, PPA-Glu, PIIA-Asp, PPA-Phe, PPA-Ile, and PPA-Ala, respectively). The polymers were prepared by the polymerization of the N-(4-ethynylphenylcarbamoyl)-L-amino acids ethyl ester (PA-Leu, PA-Glu, PA-Asp, PA-Phe, PA-Ile, and PA-Ala) using Rh+(2,5-norbornadiene)[(eta(6)-C6H5)B-(C6H5)(3)] (Rh(nbd)BPh4) as the catalyst. The biased helical conformations of all the urea-functionalized polymers were demonstrated through Cotton effects in the circular dichroism (CD) spectra. The addition of various ammonium salts including tetra-n-butylammonium acetate (TBAA), benzoate (TBAB), nitrate (TBAN), azide (TBAN(3)), fluoride (TBAF), chloride (TBACl), and bromide (TBABr) to,I solution of all the urea-functionalized polymers intensified the CD responses of the polymers, indicative of the chiral adjustability of the anion recognition using urea groups. The anion signaling property of the urea-functionalized polymers was different from each other. In particular, the signs of the induced Cotton effect for the urea-functionalized polymers in the presence of anions were strongly dependent on the pendant Structure of the alpha-amino acids.