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Side-chain functionalized glycopolymers have been successfully prepared in a well-controlled manner via a copper(0)-catalyzed one-pot reaction combining living radical polymerisation and ‘click chemistry’. The polymerisation was confirmed by the first-order kinetic plots, the linear relationships between molecular weights and the monomer conversions while keeping relatively narrow polydispersity (<1.33). The click conversion and polymerisation conversion versus reaction time plots for a Cu(0)-catalyzed one-pot reaction elucidate that the rates of click reaction are significantly faster than the polymerisation rates. Modified gold nanorods (GNRs) with glycopolymeric coatings were prepared through the interaction of Au–S bonds and the glycopolymer substituted GNRs showed strong, specific molecular recognition abilities with lectin (PNA).