Cation-Dependent Fluorescent Properties of Naphthalimide Derivatives with N-Benzocrown Ether Fragment

Abstract

The investigation of N-phenyl-4-amino- and N-phenyl-4-acetamido-1,8-naphthalimides containing N-benzo-15-crown-5 ether substituent showed that the presence of ionophoric fragment as N-substituent in naphthalimide molecule provides the design of compound possessing the properties of fluorescent receptor. The addition of metal cations does not change the position of absorption and emission bands but substantial increases the fluorescence intensity. The study of molecules included the theoretical and experimental (optical, NMR) methods, analysis of intramolecular charge (electron) transfer and fluorescence properties in the presence and absence of metal ions.

Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors

“…[21][22][23] It is thus no surprise that this structure has found application in the field of anion recognition and sensing, and in the last seven years or so many excellent examples of naphthalimide-based anion sensors have been published, clearly demonstrating the versatility of this structure within this fast growing field of research.…”

Synthesis, Optical Characteristics and Complex Formation of Molecular Receptors Based on 1,8-Naphthalimide Derivatives in Solution and in Composition of Hybrid Tin Dioxide Nanoparticles

“…The former observation of naphthalimide containing oxocrown ether in N-aryl moiety [23] by X-ray crystallography method showed Molecular Receptors Based on 1,8-Naphthalimide Derivatives the dihedral angle between the naphthalimide moiety and N-aryl group to be close to 90°. Thus, one can conclude that the π-electronic interaction between these two fragments is very weak and negligible in the ground state.…”

“…It was shown also that the presence of crown ether group in the N-aryl moiety of naphthalimide leads to dramatic decrease of emission intensity with respect to crown free N-phenylnaphthalimide due to efficient electron transfer between naphthalimide chromophore and receptor unit. [23,24] Upon the addition of metal ions the lone pair of electrons of crown ether receptor's heteroatoms are engaged in cation binding, this suppresses PET process and causes fluorescence enhancement (Scheme 5).…”

FRET versus PET: ratiometric chemosensors assembled from naphthalimide dyes and crown ethers

“…29,30 A few chemosensors for metal cations and protons containing aminonaphthalimide and rhodamine units in which spirolactam to ring-open amide equilibrium of rhodamine dyes is used to switch FRET from the amino-naphthalimide fragment were studied. [41][42][43] These compounds displayed pronounced enhancement of emission intensity by coordination with metal cations, which was a result of inhibition of PET between crown ether receptor conjugated with N-phenyl ring and fluorophore. Structure of compounds MNI1-7 and BNI1- 3 We recently developed monochromophoric amino-and amido-naphthalimide derivatives MNI4-6 (Scheme 1) bearing crown ether groups as fluorescent sensors exploiting process of photoinduced electron transfer.…”