A Naphthalene Diimide Based Macrocycle Containing Quaternary Ammonium Groups: An Electron‐Deficient Host for Aromatic Carboxylate Derivatives

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, 1H 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.

Fine-Tuning the Electronic Properties of Azo Chromophore-Incorporated Perylene Bisimide Dyads

“…All azo-PBIs showed aggregation-induced emission quenching (AIQ) above 25 μM in chloroform, 46,47 thus all spectra were recorded at 12.50 μM to minimize the aggregation effects on the optical properties. Concentration-dependent emission spectra for all compounds are given in the Supporting Information (Figures S34−S41).…”

Water-soluble organic macrocycles based on dye chromophores and their applications

“…In addition, a water-soluble macrocycle 6 4+ as an organic or inorganic anion sensor in aqueous solution was reported by Valiyaveettil's group. 19 Macrocycle 6 4+ contains two NDI moieties and four quaternary ammonium centers that promote its water-solubility (Fig. 2b).…”

“…Since 2019, a series of water-soluble organic macrocycles have been constructed based on dye chromophores including naphthalene diimide (NDI), 16–19 perylene diimide (PDI), 20,21 azobenzene (azo), 22–24 tetraphenylethylene (TPE), 25–29 anthracene 30–32 and so on. In this paper, we select some examples from them and introduce their structural characteristics.…”