Synthesis and Fluorescent Property Study of Novel 1,8-Naphthalimide-Based Chemosensors

Abstract

A series of novel mono- and di-substituted N-n-butyl-1,8-naphthalimide derivatives were synthesized simultaneously via a three-step reaction. The single crystal structure of N-n-butyl-4-[N′,N′-bis(2′,4′-dichlorobenzoyl)ethylamino]-1,8-naphthalimide (3f) was determined. The UV-vis and fluorescence properties of compound 3f were investigated. The 3f showed highly selective and sensitive fluorescence changes response towards Pb2+. A titration of monomer with Pb2+ ion was performed. When Pb2+ ion concentration increased from 0 to 10 eq., the fluorescent intensity of 3f decreased from 199.97 to 48.21. The pH effect on 3f showed that it is stable in a wide range of pH. The results indicated that 3f might be a probe molecule for Pb2+.

A systematic review on 1,8-naphthalimide derivatives as emissive materials in organic light-emitting diodes

“…NI derivatives have been utilized in different applications including laser active media, fluorescence switchers, fluorescent markers in biology, photoinduced electron transfer sensors, ion probes [57,58], etc. Attractive derivatives can be created from NI skeleton, which can display strong fluorescent emission on irradiation, and their rich photophysical properties enable them to function as prime molecular entities for use in optoelectronic devices [59,60]. The presence of electron-deficient center in NI derivatives generally permit them to achieve high electron affinity, which validates their usage as HBL in OLEDs [61,62].…”

Functional aromatic polyamides for the preparation of coated fibres as smart labels for the visual detection of biogenic amine vapours and fish spoilage

“…According to literature, bromonaphthalimides react with amines rendering coloured arylamines by nucleophilic aromatic substitution of the halide. [26][27]28 Thus, the chemical reaction and the evolution of colour can be used to detect amines. Accordingly, we thought that polymers with bromonaphthalimides moieties could be worth to prepare sensory material and we designed aromatic polyamides containing these moieties.…”

Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing

“…[ 1 , 2 , 3 , 4 , 5 ]. These versatile characteristics make naphthalimides potential materials for fluorescent sensors and molecular switchers, laser active media, light emitting diodes, dyes for natural synthetic fibers, fluorescent markers in biology, antitumor treatments, DNA targeting binders, and photoinitiators [ 2 , 3 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ]. The optical and photophysical properties of naphthalimide derivatives depend on the substituent nature of the heterocycle as well as the position of the substituents [ 2 , 17 ].…”

“…The chemical modification of the naphthalimide structure mainly on the imide N site or at the position 4 of the naphthalene moiety gives the possibility to tune their absorption and emission parameters. By substituting electron-donating groups at the C-4 position of the naphthalimides, the emission quantum yield can be usually increased and the fluorescence color can be varied from blue to yellowish-green [ 13 , 15 , 18 , 19 ]. Also, the photophysical properties of the naphthalimide derivatives can be tuned by the appropriate choice of the push-pull substituents at imide nitrogen and C4 position at naphthalene ring due to the intramolecular charge transfer in this system [ 18 , 20 , 21 ].…”

“…Naphthalimide derivatives are very attractive to be used as photoactive components in colorimetric and fluorometric chemosensors due to the great diversity of their photophysical characteristics. Therefore, the naphthalimide compounds have been applied to detect different metal ions such as Cu 2+ , Zn 2+ , Hg 2+ , Ag + , Fe 3+ , Cr 3+ , or fluoride ion [ 13 , 22 , 23 , 24 , 25 ]. Also, naphthalimide derivatives were explored successfully for monitoring hypochlorous acid and hypochlorite [ 26 , 27 , 28 ].…”