Self-complementary and narcissistic self-sorting of bis-acridinium tweezers

Abstract

A molecular tweezer incorporating two acridinium moieties linked by a 1,3-dipyridylbenzene spacer was synthesized in three steps. The formation of its self-complementary dimer in water was demonstrated as a result of π–π stacking and hydrophobic interactions. Moreover, a 1 : 1 mixture of this bis-acridinium tweezer with one built on a 2,6-diphenylpyridyl spacer evidenced its narcissistic self-sorting behaviour in water.