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A Naphthalene Diimide Based Macrocycle Containing Quaternary Ammonium Groups: An Electron‐Deficient Host for Aromatic Carboxylate Derivatives
Author(s) -
Türel Tankut,
Valiyaveettil Suresh
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000258
Subject(s) - chemistry , diimide , acetonitrile , carboxylate , titration , photochemistry , cyclophane , naphthalene , polymer chemistry , stereochemistry , organic chemistry , molecule , perylene
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.