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Au@poly(N-propargylamide) Nanoparticles: Preparation and Chiral Recognition

Chaohong Zhang,Ci Song,Wantai Yang,Jianping Deng

This communication reports the first gold nanoparticles (NPs) chirally functionalized with optically active helical substituted polyacetylene (the resulting hybrid particles are defined as Au@PPA NPs). The novel nanoparticles consist of gold as core and optically active helical poly( N -propargylamide) as shell and show considerable optical activity derived from helical poly( N -propargylamide) chains with predominantly one-handed screw sense. The Au@PPA NPs are prepared by a three-step approach: i) a thiol-containing N -propargylamide monomer [M th , HC≡CCH 2 NHCO(CH 2 ) 10 SH] is synthesized and characterized with FTIR and 1 HNMR spectroscopy and elemental analysis; ii) a copolymer (poly(M th - co -M ch )) was prepared by starting from monomer M th and another chiral N -propargylamide monomer (M ch ); poly(M th - co -M ch ) formed helical conformations and showed optical activities; and, iii) Au@PPA NPs are prepared from hydrogen tetrachloroaurate (III) and poly(M th - co -M ch ) through a one-spot procedure by using LiBH 4 as reducing agent. The as-obtained hybrid nanoparticles are characterized by FTIR spectroscopy, TEM, UV-vis absorption and circular dichroism (CD) techniques. UV-vis and CD measurements demonstrated the remarkable optical activity of the Au@PPA NPs. More interestingly, the Au@PPA NPs show much stronger UV-vis and CD sigals when compared to the corresponding orginal helical copolymer, poly(M th - co -M ch ). The chiral hybrid nanoparticles demonstrate different absorption toward (R)-(+)- and (S)-(−)-1-phenylethylamines, preferentially adsorbing the (S)-isomer.