Aliphatic amine responsive organogel system based on a simple naphthalimide derivative

Cao, Xinhua; Zhang, Tingting; Gao, Aiping; Li, Keli; Cheng, Qiuli; Song, Lijuan; Zhang, Min

doi:10.1039/c4ob00728j

Cited by 20 publications

(10 citation statements)

References 47 publications

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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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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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“…These compounds, largely because of their large, flat aromatic structure, readily participate in π- π stacking interactions within or between the molecules, enabling the “trapping” of organic solvents within the ordered structure . Moreover, because naphthalimide has a well-studied and highly tunable fluorescence emission profile, structures containing naphthalimide can be characterized via fluorescence spectroscopy and/or fluorescence-based microscopy, and supramolecular structural changes (i.e., gelation and de-gelation) can be easily detected …”

Section: Introductionmentioning

confidence: 99%

“…19 These compounds, largely because of their large, flat aromatic structure, readily participate in π-π stacking interactions within or between the molecules, enabling the "trapping" of organic solvents within the ordered structure. 20 Moreover, because naphthalimide has a well-studied and highly tunable fluorescence emission profile, 21 fluorescence-based microscopy, 22 and supramolecular structural changes (i.e., gelation and de-gelation) can be easily detected. 23 Despite the significant interest in amide-containing small molecule gelators, 24 and the known ability of naphthalimide to participate in and/or induce gelation, 25 there are only isolated instances in which amide moieties and naphthalimides have been combined in the same gelator molecule.…”

Section: ■ Introductionmentioning

confidence: 99%

Sonication-Induced, Solvent-Selective Gelation of a 1,8-Napthalimide-Conjugated Amide: Structural Insights and Pollutant Removal Applications

et al. 2021

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Reported herein is the synthesis, characterization, and dye removal applications of a highly solvent-selective organogel-forming amide, compound 1, which contains a 1,8-naphthalmide moiety, flexible n-hexyl chain, and benzene ring. This compound displayed remarkable solvent selectivity, with gel formation occurring only in the presence of alkylated aromatic solvents. Detailed structural characterization of the gels, combined with notable theoretical insights, is invoked to explain the highly selective gelation properties of compound 1, as is a comparison to non-gel forming structural isomer 2, which contains the same structural elements in a different arrangement. Finally, the ability of the gel derived from compound 1 to act as a reusable material for the efficient removal of cationic organic dyes from contaminated aqueous environments is also reported, with up to 11 repeated uses of the gel still maintaining the ability to effectively remove Rhodamine B.

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“…47 We have reported a series of 1,8-naphthalimide derivatives as gelators, which are sensitive to amine and toxic nitrite anions in the gel state. 48,49 NACs have an obvious characteristic of electron deficiency and are prone to interact with electron-rich organic fluorescent molecules. Herein, we have incorporated 4-pyridinol and phenol into the 1,8-naphthalimide-based gel molecule (G-P and G-B in Scheme 1) to generate two novel fluorescent gelators with the ability of visual detection of TNP in solution and in the gel state.…”

Section: ■ Introductionmentioning

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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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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Aliphatic amine responsive organogel system based on a simple naphthalimide derivative

Cited by 20 publications

References 47 publications

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

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

Sonication-Induced, Solvent-Selective Gelation of a 1,8-Napthalimide-Conjugated Amide: Structural Insights and Pollutant Removal Applications

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

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