Synthesis, binding and self-assembly properties of a well-defined pillar[5]arene end functionalised polydimethylacrylamideElectronic supplementary information (ESI) available. See DOI: 10.1039/c5py01186h

The synthesis, binding and self-assembly properties of a well-defined pillar[5]arene end-functionalised poly(dimethylacrylamide)( MePilla-PDMAC ) are reported. In order to synthesise MePilla-PDMAC , a new trithiocarbonate type RAFT agent MePilla-CTA was developed incorporting a partially methylated pillar[5]arene moiety. Kinetic studies clearly indicated the propensity of MePilla-CTA to control the polymerisation of DMAC. Interestingly, as PDMAC type chains display good solubilty both in organic and aqueous media, MePilla-PDMAC was able of specifically bind electron deficient guest molecules at the α-chain-end both in chloroform and water. Complex formation was found to be reversible upon addition of chloride anions or heating in organic and aqueous media, respectively. Furthermore, cryo-TEM, VT-NMR ( 1 H) and VT-DLS investigations also indicated the ability of MePilla-PDMAC to self-assemble into micelle-like aggregates in water showing reversible recognition properties. The synthesis, binding and self-assembly properties of a well-defined pillar[5]arene end functionalised polydimethylacrylamide are reported.