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The synthesis of gold nanoparticles (2–4 nm) carrying a single functional polystyrene chain and its characterization by gel permeation chromatography are reported. This has been achieved by a new type of macromolecular azo‐initiator based on telechelic polystyrene with containing α,ω‐methylcoumarin endgroups and an azo group in the middle of the polystyrene. The structure and the near‐quantitative functionality of the initiator have been verified by performing NMR, GPC, and UV–vis measurements. This macroinitiator has been used to initiate a surface polymerization of 4‐vinylthiophenol molecules immobilized on the surface of gold nanoparticles. As a product, gold nanoparticles carrying exactly one polystyrene chain have been synthesized with functionalization degrees of up to 90% (crude yield). Proof and quantification of the functionalization degree have been demonstrated by application of a GPC setup with a diode array detector for online UV–vis spectra.

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