Organic fluorescent gel compound based on naphthalimide and preparation method and application thereof

A technology of hydroxynaphthimide and naphthalimide, which is applied in the field of supramolecular chemistry, can solve problems such as difficulties, complex synthesis, and difficult purification, and achieve the effect of sensitive detection

Inactive Publication Date: 2014-08-20
XINYANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Most of the currently studied gelling factors are compounds with complex structures, such as steroids, sugars, alkoxybenzenes, amino acids, long hydrophilic chain hydrocarbons, metal compounds, dendrimers, etc. Most of them are complicated to synthesize and difficult to purify, so it is difficult for them to enter practical application in the future.

Method used

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  • Organic fluorescent gel compound based on naphthalimide and preparation method and application thereof
  • Organic fluorescent gel compound based on naphthalimide and preparation method and application thereof
  • Organic fluorescent gel compound based on naphthalimide and preparation method and application thereof

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Embodiment

[0044] 4-Methoxy-N-hexanoyl-1,8-naphthalimide [4-CH3O-C12H5NO2-(CH2)5-COOH]: 4-bromo-p-phenylene-N-hexanoic acid-1, 8-Naphthalimide (a known compound (3g, 6.15 mmol) was dissolved in anhydrous methanol (60 mL), added K2CO3 (5g, 36.25 mmol), and heated to reflux for 10 hours. After the reaction was completed, filter and wash with dichloromethane After washing 3 times, the organic phases were combined and the solvent was removed under reduced pressure, followed by column chromatography (methanol / dichloromethane=1 / 20, v / v) to obtain a light yellow solid with a yield of 80%. 1HNMR (400 MHz, d6-DMSO, such as Image 6 shown): δ 12.018(s, 1H), 8.479 (d, J = 6.8 Hz, 1H), 8.450 (d, J = 6.0 Hz, 1H), 8.409 (d, J = 6.8 Hz, 1H), 7.771 ( t, J = 6.0 Hz, 1H), 7.283 (d, J = 6.8 Hz, 1H), 4.117 (s, 3H), 3.993 (t, J = 6.0 Hz, 2H), 2.223 (T, J = 6.0 Hz, 2H), 1.617 (m, 2H), 1.556 (m, 2H), 1.346 (m, 2H); 13C NMR (100 MHz, d6-DMSO): δ 174.96, 163.96, 163.32, 160.73, 133.66, 131.42, 128.94, 128.63,...

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Abstract

The invention discloses an organic fluorescent gel compound based on naphthalimide. The compound is alkyl chain carboxylic acid 4-hydroxyl-N-caproyl-1,8-naphthalimide with 4-hydroxy naphthalimide as a chromophore, and has a structural formula as below, and a molecular formula of [6-HO-C12H5NO2-(CH2)5-COOH]. The invention uses simple fatty acids to introduce the naphthalimide group with fluorescence property, and provides a novel simple gel system; at the same time, the gelator has response function to triethylamine, addition of triethylamine results in fluorescence quenching, and addition of a certain amount of acid generates fluorescence recovery, therefore the invention uses this property, to realize sensitive detection of tri ethylamine by the gel system.

Description

technical field [0001] The invention belongs to the technical field of supramolecular chemistry, and specifically relates to a naphthalimide-based organogel compound and a preparation method thereof, as well as an organogel obtained from the organogel compound and applications thereof. Background technique [0002] Organogels are colloids formed by the intermolecular non-covalent bond interaction of gelling factors and the mutual synergistic effect and encapsulation of various organic solvents. This organogel has both the rheology of a solid (with a certain viscosity and elasticity) and the homogeneity of a liquid, and exhibits good dynamic reversibility and spontaneous actuation behavior. Because organogels can respond to external stimuli, they have broad application prospects in drug sustained release, cell culture, smart molecular devices, biomimetic materials, sensing, and light harvesting. In addition, organogels construct multi-dimensional and multi-scale micro-nano m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/643
Inventor 曹新华宋力归风铁高爱萍
Owner XINYANG NORMAL UNIVERSITY
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