Abstract
Naphthalene diimide (NDI) compounds are widely used as electron acceptors in various applications. Herein, we combine NDI with quaternary ammonium groups for the synthesis of a highly electron-deficient linear compound 2 and macrocycle 3. The complexation studies of the water-soluble macrocycle 3 with aromatic di- and tetra- carboxylate anions in water were done using absorption, emission, 1 H NMR and NOESY spectroscopic titrations. The NDI incorporated macrocycle 3 showed high binding affinities towards linear aromatic tetracarboxylate anions owing to the size and charge complementarity of the host-guest complex. Macrocycle 3 binds tetracarboxylate anion much better than dicarboxylate anions. Furthermore, the macrocycle 3 is solvated differently in acetonitrile and in water or dimethyl sulfoxide, which induces changes in conformation and photophysical properties. Such electron-deficient optically active macrocycles are useful for developing useful sensor materials.
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