Aggregation-induced emission enhancement characteristics of naphthalimide derivatives and their applications in cell imaging

Abstract

Novel naphthalimide derivatives (NIM) with donor-acceptor architecture were successfully constructed and their unique fluorescent properties were investigated. In particular, the fluorescence intensities of 4-methoxystyrene substituted NIM-1 were solvent independent and its quantum yields varied from 0.4 in toluene to 0.52 in MeOH. However, 4-(N,N-diphenylamino) styrene substituted NIM-2 and 4-nitrostyrene substituted NIM-3 exhibited low luminescence in dilute solutions but were efficiently fluorescent under conditions of molecular aggregation. NIM-2 showed strong solid fluorescence with a longer wavelength emission and larger Stokes shift. In addition, NIM-3 showed unexpected blue-green fluorescence due to the formation of fluorescent organic nanoparticles (FONs) under mixed solution. These two cases were ascribed to the aggregation-induced enhanced emission (AIEE) effects and which can also reasonably explain the bright cellular images observed when cells were incubated with NIM-2 and NIM-3. Furthermore, compound NIM-2 can be used to recognize cancer cells owing to its subcellular behaviour

Synthesis and sensor propeties of crown-containing derivatives of 4-(1,5-diphenyl-Δ2-pyrazolin-3-yl)-1,8-naphthalimide

“…At the same time, in recent years, it has been shown that distinct advantages in the development of optical sensors arise upon using fluorophores having a longer wavelength position of bands in fluorescence spectra and higher value of the Stokes shift [18,19]. The possibility of conducting analysis under conditions relating to biological objects; of determination of cat ions of the d block elements, the coordination com pounds of which often have absorption bands in the vis ible region; and of decreasing the measurement errors related to fluorescence self absorption and scattering of exciting light are to be considered such advantages first and foremost.…”

Multifunctional Nanoparticles Self‐Assembled from Small Organic Building Blocks for Biomedicine

“…Stable fluorescent nanoparticles from a self‐assembled small π‐conjugated compound DPA‐TSB (Figure ) were also developed by Ma and co‐workers, showing good cell‐staining ability. Other types of π‐conjugates that afford nanoparticle formation are shown in Figure …”

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

“…After the reaction mixture was cooled to room temperature, the catalyst was filtered off, the filtrate was evaporated in vacuo. The residue was purified by column chromatography (silica gel, eluent PhH-EtOH, gradient elution) to yield 23 mg (16 % (1) 6-(2- (2,3,5,6,8,9,11, [1,4,10,7,13] …”

“…Derivatives of 1,8-naphthalimide are an important class of organic luminophores, which are widely used as optical brighteners, [5] laser dyes, [6] solar cells elements, [7] fluorescent markers in biology, [8] electroluminescent materials, [9] anticancer drugs, [10] fluoroscent crack detection reagents.…”