Changing π-Interactions and Conformational Adjustments of N-(Isonicotinylhydrazide)-1,8-naphthalimide by Hydration and Complexation Affect Photophysical Properties

Abstract

Noncovalent self-assemblies of different forms of a 1,8-naphthalimide derivative N-(isonicotinylhydrazide)-1,8-naphthalimide adopt different conformational adjustments due to the interplay of weak interactions. In such assemblies stacking interactions significantly contribute to direct the orientations of tether, which also influenced packing patterns. Effects of weak noncovalent interactions are reflected in the physicochemical properties of solvate and metal complexes of this naphthalimide derivative. Dual fluorescence emissions were observed from hydrate and silver complex of N-(isonicotinylhydrazide)-1,8-naphthalimide, which was not observed in anhydrous form of the compound. These results are compared with fluorescence emission study performed with solution of N-(isonicotinylhydrazide)-1,8-naphthalimide. Aggregation induced fluorescence emission of a solution in DMSO was caused by adding water. This emission in solution occurred at a much different emission wavelength than the emission observed from the hydrated sample in the solid state. It is also established that the aggregation induced fluorescence of N-(isonicotinylhydrazide)-1,8-naphthalimide caused by adding water to a solution of the compound in dimethyl sulfoxide can be quenched by different nitro-phenols.

ICT and AIE Characteristics Two Cyano-Functionalized Probes and Their Photophysical Properties, DFT Calculations, Cytotoxicity, and Cell Imaging Applications

“…Nowadays, AIE and AIEE active materials have been extensively used for their potential applications in biomedical science [19], in ions and explosive compounds detection [20,21], as an optoelectronic material [22], in the detection of active biomolecules [23], or in the detection of hazardous materials [24,25]. The fluorescent properties of some fluorophores are quenched because of intramolecular charge transfer (ICT) or the PET effect and become highly fluorescent on suppression of these effects in their aggregation state [26,27].…”

Stacking among the clips of the poly-aromatic rings of phenazine with hydroxy-aromatics and photophysical properties

“…[36][37][38][39][40][41][42][43] The solvent molecules within lattices are of concern in discerning optical properties. 44 Thus, the structures of self-assemblies are of general concern in the elucidation of photoluminescence properties. The dimer-like emissions [45][46][47] and Förster resonance transfer emission 48 require designs to hold the uorophores in close proximity in denite orientations.…”

Changes in Emission Properties by π‐Stacking and Conformation Adjustment of an Imidazole‐Tethered Naphthalimide Derivative

“…Modulation of fluorescence of naphthalimide derivatives can be caused by interacting with ions and neutral molecules . We have been studying molecular recognitions, ion recognitions and conformational aspects of imide containing compounds that have nitrogen based heterocyclic units attached through flexible tethers . Those studies have been carried out with a philosophy that a flexible tether either keeps away or brings close to a fluorophore from an interacting group located at a remote site.…”