Tetraphenylethylene[3]arene: synthesis, structure, and sensing of I−

Abstract

A novel luminous macrocyclic arene, named tetraphenylethylene[3]arene 1, was conveniently synthesized by Lewis acid-promoted one-pot condensation of 1,1′,4,4′-tetramethoxytetraphenylethylene and paraformaldehyde in dichloromethane at room temperature. 1 showed a unique stretched hexagon structure and exhibited strong bright blue fluorescence both in the solid state and THF–H₂O mixtures with water f_w ≥ 60%. In particular, it was found that 1 exhibited exceptional performance in selective sensing of I⁻ ions among other anions such as AcO⁻, NO₃⁻, ClO₄⁻, HSO₄⁻, F⁻, Cl⁻, Br⁻, PF₆⁻, H₂PO₄⁻, BF₄⁻ and CO₃F₃S⁻.