Complexation of Paraquat and Diazapyrenium Derivatives with Dipyrido[30]crown‐10

Abstract

Abstract A new pyridine‐containing crown ether, dipyrido[30]crown‐10 (DP30C10), has been synthesized and has been shown to form [2]pseudorotaxanes spontaneously with paraquat derivatives in solution, as demonstrated by proton NMR spectroscopy and mass spectrometry, and in the solid state, as proved by single‐crystal X‐ray analysis. The complexation between DP30C10 and N , N′ ‐dimethyl‐2,7‐diazapyrenium bis(hexafluorophosphate) was also investigated, and was found to have an association constant of 8.2 × 10 3 M –1 in acetonitrile. Based on this recognition motif, a dual‐action acid/base and base/acid‐controllable molecular switch was demonstrated.