Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Imidazole-like ionic salt with electron donor-acceptor structure, preparation method and use thereof

A push-pull electron and ionic salt technology, applied in the field of nonlinear optical materials and ionic salts, can solve the problems of limited practical application, poor processability, low thermal stability, etc., and achieves simple reaction and post-processing operations, high product purity, The effect of good application prospects

Inactive Publication Date: 2008-03-19
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantages are low thermal stability and poor processability, which limit the practical application of organic NLO crystal materials (J.Am.Chem.Soc., 2003, 125, 15651)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Imidazole-like ionic salt with electron donor-acceptor structure, preparation method and use thereof
  • Imidazole-like ionic salt with electron donor-acceptor structure, preparation method and use thereof
  • Imidazole-like ionic salt with electron donor-acceptor structure, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: Preparation of N-(p-methoxyphenyl)-N'-(2,4-dinitrophenyl) imidazole chloride salt

[0028]

[0029]Add 1 mmol of N-(p-methylphenyl)imidazole, 1.1 mmol of 2,4-dinitrochlorobenzene and 1 ml of acetonitrile into the sealed tube, tighten the plug of the sealed tube, and stir the reaction in an oil bath at 110°C for 4 hours. After the heating was stopped and the reaction system was cooled, it was filtered, and the filter residue was washed several times with ether to obtain a white solid product. Yield 90%.

[0030] 1 HNMR (CD 3 SOCD 3 ) δ (ppm) 10.37 (s, 1H, --- NH), 9.06 (d, 1H, J = 2.4Hz), 8.91 (d-d, 1H, J = 2.4Hz, J = 8.7Hz), 8.55 (S, 1H) 8.40(s, 1H), 8.37(s, 1H), 7.83(d, 2H, J=8.4Hz), 7.23(d, 2H, J=8.4Hz), 3.85(s, 3H, OCH 3 ) MS (ESI) M / Z (%) 314.2 (M + )IR (KBr) v3402, 3140, 3021, 2886, 2771, 1849, 1665, 1618, 1508, 1358, 1250, 1078, 1017, 953, 897, 860, 773, 662, 530

[0031] UV (ethanol, alcohol): λ (max) = 265nm

[0032] EA. Found: C, 50.78;...

Embodiment 2

[0033] Embodiment 2: the preparation of N-phenyl-N'-(2,4-dinitrophenyl) imidazolium chloride salt

[0034]

[0035] Add 1 mmol of N-phenylimidazole, 1.1 mmol of 2,4-dinitrochlorobenzene and 1 ml of acetonitrile into the sealed tube, tighten the plug of the sealed tube, and stir the reaction in an oil bath at 110°C for 2 hours. After the heating was stopped and the reaction system was cooled, it was filtered, and the filter residue was washed several times with ether to obtain a white solid product. Yield 82%.

[0036] 1 HNMR (D 2 O) δ (ppm) 9.21 (s, 1H), 8.77 (d, 1H, J = 9.6HZ), 8.09 (br, 2H,) 7.95 (s, 1H), 7.61 (m, 5H) MS (ESI) M / Z(%)311.2(M + )IR (KBr) v3029, 2878, 2785, 1859, 1607, 1549, 1494, 1457, 1350, 1260, 1147, 1085, 899, 837, 778, 760, 738, 688, 653, 521.

[0037] UV (alcohol): λ (max) = 237nm

[0038] EA. Found: C, 52.00; H, 3.24; N, 16.38; Theoretical: C, 51.96; H, 3.20; N, 16.16.

Embodiment 3

[0039] Embodiment 3: Preparation of N-(p-methylphenyl)-N'-(2,4-dinitrophenyl) imidazolium chloride salt

[0040]

[0041] Add 1 mmol of N-(p-methylphenyl) imidazole, 1.1 mmol of 2,4-dinitrochlorobenzene and 1 ml of acetonitrile into the sealed tube, tighten the plug of the sealed tube, and stir the reaction in an oil bath at 110°C for 12 hours. After the heating was stopped and the reaction system was cooled, it was filtered, and the filter residue was washed several times with ether to obtain a white solid product. Yield 87%.

[0042] 1 HNMR (D 2 O) δ (ppm) 9.21 (s, 1H), 8.78 (d, 1H, J = 8.4Hz), 8.11 (d, 1H, J = 8.4Hz) 8.07 (S, 1H), 7.97 (s, 1H) 7.54 (d, 2H, J=8.4Hz), 7.56(d, 2H, J=8.4Hz) 2.36(s, 3H, CH 3 )

[0043] MS(ESI)M / Z(%)325.2(M + )

[0044] IR(KBr)v3495, 3247, 3167, 3058, 2778, 1983, 1774, 1621, 1508, 1357, 1242, 1067, 956, 911, 815, 739, 651, 624, 523

[0045] UV (alcohol): λ (max) = 238nm

[0046] EA. Found: C, 53.16; H, 3.68; N, 15.31; Theoretical: C, ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a new imidazole ion salt with a push-pull electronic structure and a preparation method, which can be applied to the field of nonlinear optical materials in the class of organic crystal. According to a certain molar ratio, electronic radicel-substituted aryl N-substituted imidazole reacts with electron-attracting radicel-substituted halogenated aromatic hydrocarbon under organic solvent and reaction temperature, so that the imidazole ion salt with the push-pull electronic structure is produced. Moreover, the negative ions of the ion salt are exchanged with other negative ions, so that a series of ion salts with the push-pull electronic structure can be produced. The imidazole ion salt with the push-pull electronic structure of the invention is a new class of ion salts, and as a nonlinear optical material, has a big nonlinear optical coefficient and high thermal stability. The synthesis method of the invention is characterized in simple reaction and post-processing operation, high purity of products, etc.

Description

technical field [0001] The invention relates to the fields of nonlinear optical materials and ionic salts, in particular to a new type of imidazole ionic salt compound with a push-pull electronic structure and a preparation method thereof. Background technique [0002] Nonlinear optical materials have been a hot spot in the field of materials research in recent decades. Such materials not only play a vital role in solid-state laser technology as frequency conversion materials, but also are widely used in information transmission, storage, extraction, processing and display technologies. The existing nonlinear optical materials can be roughly divided into the following three categories according to their chemical composition and physical properties: inorganic substances, organic substances and inorganic-organic composite materials. One category of organic matter is divided into two categories: organic crystals and organic polymers. The advantages and disadvantages of organi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D233/64G02F1/361
Inventor 肖吉昌姜明月陈超森
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com