An amphiphilic [2]biphenyl-extended pillar[6]arene: Synthesis, controllable self-assembly in water and application in cell-imaging

Synthesis and functionalization of novel macrocyclic host molecules are important topics in supramolecular chemistry. In this work, the first amphiphilic [2]biphenyl-extended pillar[6]arene (AM-[2]BP-ExP6) was designed and synthesized with poly(ethylene glycol) chains as the hydrophilic tails and a rigid cavity as the hydrophobic core. Due to its amphiphilic nature, AM-[2]BP-ExP6 could self-assemble to stable fibers in water. What's more, AM-[2]BP-ExP6 could associate with quaternary ammonium modified tetraphenylethylene guest (QTPE) to form a 2:1 host-guest complex, accompanied by significant enhanced fluorescence. Interestingly, different like AM-[2]BP-ExP6, AM-[2]BP-ExP6⊃QTPE host-guest complex self-assembled into fluorescent particles with diameter about 310 nm, the obtained fluorescent particles can be further employed in living cell imaging. [Display omitted] The first amphiphilic [2]biphenyl-extended pillar[6]arene was designed and synthesized successfully, which showed controllable self-assembly property in water and can be further applied in living cell imaging.