This research aims to synthesize a dopamine-functionalized macromolecular anchor to perform surface modification on the target nanostructures. A molecular anchor, 3,4-dichloro-1-[2-(3,4-dihydroxyphenyl)ethyl]-1H-pyrrole-2,5-dione, was successfully synthesized from dopamine and 2,3-dichloromaleic anhydride. The anchor acted as a linkage to couple the chains of poly(pentafluorostyrene) (PPFS) which were synthesized via reversible addition fragmentation chain transfer (RAFT) polymerization. Modification was successfully performed to silver nanoparticles (AgNPs) by deposition of the dopamine-functionalized coupled PPFS onto the surface of the particles. The modified AgNPs had demonstrated improved dispersibility in organic solvent due to the hydrophobic nature of PPFS. To modify the surface chemistry of the nanoparticles further, thioglucose was grafted onto the structure of the coupled PPFS via thiol-fluoro nucleophilic substitution at the para-position of the pentafluorophenyl groups on the monomer units. The presence of sugar moieties on the coupled PPFS increased its hydrophilicity, which allowed the modified AgNPs to be readily dispersed in aqueous solvent.