Triphenylamine-based receptor for selective recognition of dicarboxylates

A new triphenylamine-based receptor 1 has been designed and synthesized for the recognition of aliphatic dicarboxylates of various chain lengths. This receptor has been designed to utilize an amide–urea conjugate for binding dicarboxylates. The receptor 1 is found to bind the dicarboxylates with moderate binding strength under a semi rigid, propeller shaped, fluorescent triphenylamine spacer. The binding behavior was studied in CH3CN using 1H NMR, fluorescence and UV–vis spectroscopic methods. The conformational behavior of 1 and its complexation modes have been investigated using classical and quantum mechanical theoretical methods. The receptor is found to be selective for long chain suberate.