NDI-integrated rotaxane/catenane and their interactions with anions

Abstract

Complexation of alkali and alkaline earth metal ions with the heteroditopic Phen-ester oxy-ether macrocyclic wheel (PhenMC) is established for the synthesis of interlocked molecular systems. The single crystal X-ray structure of Na-bound PhenMC confirms the hexacoordinated geometry around the Na ion in the macrocycle. Further, Ca-ion-bound PhenMC (Ca-PhenMC) is explored with a fluorophoric azide-terminated NDI (naphthalene diimide) axle (NDIAz) for the synthesis of fluorophoric [2]rotaxane (NDIROT) and [2]catenane (NDICAT) via Cu(I)-catalyzed cycloaddition reaction. Characterizations of these two new interlocked molecular systems are performed by ESI-MS, NMR, UV-vis and PL spectroscopic studies wherever applicable. Moreover, the new molecular systems are explored towards anion sensing applications via colorimetric, UV-vis-NIR, PL and other spectroscopic studies.