Bis-naphthalimides self-assembly organogel formation and application in detection of p-phenylenediamine

Cao, Xinhua; Zhao, Na; Gao, Aiping; Lv, Haiting; Jia, Yuling; Wu, Ren-Miao; Wu, Yongquan

doi:10.1016/j.msec.2016.08.079

Cited by 20 publications

(9 citation statements)

References 35 publications

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“…Therefore, the gel system could be potentially manipulated like solids, and the gel system itself could intimately contact with environmental liquid phases because of their high surface areas and rapid internal diffusion kinetics. We had reported several gel systems with the ability of detecting cysteine and amine in the gel state. , Herein, the gel G-P was used as the smart material for TNP removal from water. The gel G-P was prepared using 5 mg of G-P gelator and 400 μL of a mixed solvent of acetonitrile/H 2 O (1/1, v/v).…”

Section: Resultsmentioning

confidence: 91%

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Strong Blue Emissive Supramolecular Self-Assembly System Based on Naphthalimide Derivatives and Its Ability of Detection and Removal of 2,4,6-Trinitrophenol

Cao

Zhao

et al. 2017

Langmuir

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Two simple and novel gelators (G-P with pyridine and G-B with benzene) with different C-4 substitution groups on naphthalimide derivatives have been designed and characterized. Two gelators could form organogels in some solvents or mixed solvents. The self-assembly processes of G-P in a mixed solvent of acetonitrile/HO (1/1, v/v) and G-B in acetonitrile were studied by means of electron microscopy and spectroscopy. The organogel of G-P in the mixed solvent of acetonitrile/HO (1/1, v/v) formed an intertwined fiber network, and its emission spectrum had an obvious blue shift compared with that of solution. By contrast, the organogel of G-B in acetonitrile formed a straight fiber, and its emission had an obvious red shift compared with that of solution. G-P and G-B were employed in detecting nitroaromatic compounds because of their electron-rich property. G-P is more sensitive and selective toward 2,4,6-trinitrophenol (TNP) compared with G-B. The sensing mechanisms were investigated by H NMR spectroscopic experiments and theoretical calculations. From these experimental results, it is proposed that electron transfer occurs from the electron-rich G-P molecule to the electron-deficient TNP because of the possibility of complex formation between G-P and TNP. The G-P molecule could detect TNP in water, organic solvent media, as well as using test strips. It is worth mentioning that the organogel G-P can not only detect TNP but also remove TNP from the solution into the organogel system.

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Section: Resultsmentioning

confidence: 91%

“…We had reported several gel systems with the ability of detecting cysteine and amine in the gel state. 46,76 Herein, the gel G-P was used as the smart material for TNP removal from water. The gel G-P was prepared using 5 mg of G-P gelator and 400 μL of a mixed solvent of acetonitrile/H 2 O (1/1, v/v).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Strong Blue Emissive Supramolecular Self-Assembly System Based on Naphthalimide Derivatives and Its Ability of Detection and Removal of 2,4,6-Trinitrophenol

Cao

Zhao

et al. 2017

Langmuir

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“…MeOH xerogel film possesses the largest WCA (132°), whereas cyclohexane xerogel film possesses the smallest WCA (100°). The wettability of the xerogel film is usually a result of the chemical composition and the xerogel microstructure [46] . The difference in the WCAs herein may result from the combined effects of molecular hydrophobicity and the xerogel morphology.…”

Section: Resultsmentioning

confidence: 99%

“…The wettability of the xerogel film is usually a result of the chemical composition and the xerogel microstructure. [46] The difference in the WCAs herein may result from the combined effects of molecular hydrophobicity and the xerogel morphology. The tunable wettability also suggests that the organogels could be cast into coating films with on-demand wettability surfaces.…”

Section: Wca Testmentioning

confidence: 99%

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

et al. 2022

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The development of low molecular‐weight gelators for the construction of stimuli‐responsive gels is increasing attention because of the great application potential. In this work, we report the design and synthesis of two new naphthalimide derivatives, GSSN and GN, as supramolecular organogelators. GSSN contains a disulfide bond in the molecule, while GN contains no disulfide bond. As a result, only GSSN exhibited reduction responsiveness. A series of tests, including UV‐vis, temperature‐dependent 1H NMR, XRD, and SEM, were carried out to characterize the gelation capability and probe into the gelation mechanism. Results showed that GN can gelate more organic solvents than GSSN. Both hydrogen bonding and π stacking contribute to the gelation. Due to the difference in the assembly of the organogelator molecules, the organogels formed by GSSN and GN presented distinct morphologies. Moreover, strong hydrophobicity was found in the organogel films of GSSN and GN, suggesting potential application as hydrophobic coating materials.

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“…The principal difference between the HOMO of N-4 and that of deprotonated N-4 was that the negative ions of oxygen of deprotonated N-4 had a higher electron cloud Fluorescent probes toward organic amines had been reported in many previous works. [22][23][24][25]29 Few ratiometric fluorescence probes for organic amines have been reported. Some frequently used organic amines including 4-chloroaniline, pyridine, aniline, TEA, diethylamine, ethylenediamine, and n-butylamine were used to verify the response performance of this self-assembly system.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Sensing Organic Amines and Quantitative Monitoring of Intracellular pH Change Using a Fluorescent Self-Assembly System

Cao

Gao

et al. 2019

ACS Appl. Polym. Mater.

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A series of supramolecular self-assembly gelators (N-4, N-12, and N-18) were designed and synthesized. N-12 and N-18 could gelate some single or mixed solvents. Microbelts and nanofibers were obtained in the self-assembly process. The hydrophobic xerogel N-18 film surface had water contact angles of 119−148.5°. Interestingly, these compounds exhibited solvatochromism properties, and compound N-18 had ratiometric detection ability toward organic amines with a detection limit for triethylamine (TEA) of 2.23 × 10 −6 M. At the same time, compound N-18 in solution and the organogel state could distinguish aromatic amines and fatty amines through its fluorescence changing. These compounds exhibited a specific pH-dependence fluorescence behavior in the the pH value range of 3−11. Compound N-4 was successfully applied to bioimaging for quantitative monitoring of pH change in cell. This work provides a new window for the preparation of self-assembly for sensitive detection organic amines and pH probes for accurate intracellular pH mapping and quantifying.

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Bis-naphthalimides self-assembly organogel formation and application in detection of p-phenylenediamine

Cited by 20 publications

References 35 publications

Strong Blue Emissive Supramolecular Self-Assembly System Based on Naphthalimide Derivatives and Its Ability of Detection and Removal of 2,4,6-Trinitrophenol

Strong Blue Emissive Supramolecular Self-Assembly System Based on Naphthalimide Derivatives and Its Ability of Detection and Removal of 2,4,6-Trinitrophenol

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

Sensing Organic Amines and Quantitative Monitoring of Intracellular pH Change Using a Fluorescent Self-Assembly System

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