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The use of 2,3,4,5,6‐pentafluorobenzyl methacrylate (PFBMA) as a core‐forming monomer in ethanolic reversible addition–fragmentation chain transfer dispersion polymerization formulations is presented. Poly[poly(ethylene glycol) methyl ether methacrylate] (pPEGMA) macromolecular chain transfer agents were chain‐extended with PFBMA leading to nanoparticle formation via polymerization‐induced self‐assembly (PISA). pPEGMA‐pPFBMA particles exhibited the full range of morphologies (spheres, worms, and vesicles), including pure and mixed phases. Worm phases formed gels that underwent a thermo‐reversible degelation and morphological transition to spheres (or spheres and vesicles) upon heating. Postsynthesis, the pPFBMA cores were modified through thiol–para‐fluoro substitution reactions in ethanol using 1,8‐diazabicyclo[5.4.0]undec‐7‐ene as the base. For monothiols, conversions were 64 …