A series of heteroditopic receptors containing halogen bond (XB) and unprecedented chalcogen bond (ChB) donors integrated into a 3,5‐bis‐triazole pyridine structure covalently linked to benzo‐15‐crown‐5 ether motifs exhibit remarkable cooperative recognition of halide anions. Multi‐nuclear 1 H, 13 C, 125 Te and 19 F NMR, ion pair binding investigations reveal sodium cation–benzo‐crown ether binding dramatically enhances the recognition of bromide and iodide halide anions, with the chalcogen bonding heteroditopic receptor notably displaying the largest enhancement of halide binding strength of over two hundred‐fold, in comparison to the halogen bonding and hydrogen bonding heteroditopic receptor analogues. DFT calculations suggest crown ether sodium cation complexation induces a polarisation of the sigma hole of ChB and XB heteroditopic receptor donors as a significant contribution to the origin of the unique cooperativity exhibited by these systems.

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The preparation of multifunctional polymer particles containing quaternary ammonium molecules by emulsion iodine transfer polymerization (emulsion ITP) via polymerization-induced self-assembly was proposed for the first time. Poly(2methacryloyloxy ethyl trimethyl ammonium chloride-dimethylamino ethyl methacrylate 12 alkyl chain length)-iodide (P(MTMA-QAC 12 ) 12 -I) was first synthesized by solution iodine transfer polymerization. It was simultaneously used as a macro-chain transfer agent and emulsifier in emulsion ITP. All conditions smoothly proceeded without coagulation, where the polymerization reached high conversion within only 4 h. When the methyl methacrylate-styrene (P(MMA-S)) copolymer was synthesized in the second block as P(MTMA-QAC 12 ) 12 -b-P(MMA-S) 462 , the water contact angle of the obtained particles was close to 90°, which was the most appropriate to use as the particulate surfactant. The P(MTMA-QAC 12 )12-b-P(MMA-S) 462 particles represented a good antimicrobial property based on the positive charge quaternary ammonium groups existing on surfaces. Using such P(MTMA-QAC 12 ) 12 -b-P(MMA-S) 462 nanoparticles (∼90 nm) at 1 wt %, the obtained cutting oil emulsion model represented high colloidal stability with approximately 50 μm oil droplet size without any coalescence. Moreover, foam formation was significantly reduced compared to the commercial cutting oil. According to their excellent properties, P(MTMA-QAC 12 ) 12 -b-P(MMA-S) 462 nanoparticles would be effectively used as a particulate surfactant in Pickering emulsion, including defoamers and antimicrobial agents.

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