Zwitter-ion with imidazole cation and malononitrile anion structure, preparation method and application thereof

An imidazolium cation and zwitterion technology, applied in organic chemistry, nonlinear optics, optics, etc., can solve the problems of large absorption wavelength and low thermal stability, and achieve simple preparation process, high nonlinear optical coefficient, and good optical transparency. Transient effects

Inactive Publication Date: 2014-07-02
XI'AN INST OF OPTICS & FINE MECHANICS - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention provides a zwitterion with imidazolium cation and malononitrile anion structure and its preparation method to solve the technical problems of low thermal stability and large absorption wavelength of existing organic nonlinear optical materials

Method used

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  • Zwitter-ion with imidazole cation and malononitrile anion structure, preparation method and application thereof
  • Zwitter-ion with imidazole cation and malononitrile anion structure, preparation method and application thereof
  • Zwitter-ion with imidazole cation and malononitrile anion structure, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Embodiments 1-6 fully reflect two synthetic processes of 4-(3-methyl-1-imidazole)-2-phenylmalononitrile zwitterion; wherein, for the intermediate product 4-(3-methyl-1 The preparation of -imidazole)-2-phenylmalononitrile, two routes are given: embodiment 1,3 or embodiment 2,4.

Embodiment 7-10

[0034] Examples 7-10 fully reflect the synthesis process of 1-methyl-3-(2,6-dimethyl-4-malononitrile anionyl)phenyl-2,4,5-trimethylimidazole;

[0035] Examples 11-14 fully demonstrate the synthesis process of 1-methyl-3-(2,6-dimethyl-4-malononitrile anionyl)phenyl-2,4,5-triphenylimidazole.

[0036] Example 1: Synthesis of 1-(4-bromobenzene)-imidazole

[0037]

[0038] 8.601 g (0.050 mol) of 4-bromoaniline, 25 ml of methanol, and 7.383 g of 40% glyoxal aqueous solution (containing 0.051 mol of glyoxal) were added to a 250 ml three-necked flask, and the mixture was stirred at room temperature for 16 h. Then 5.349 g (0.100 mol) NH was added in sequence 4 Cl, 8.108 g of 37% aqueous formaldehyde solution (containing 0.100 mol of formaldehyde), 200 ml of methanol. After stirring and refluxing for 1h, 80% H was added dropwise over 10min 3 PO 4 7ml, and then continued to stir and reflux for 8h to stop the reaction.

[0039]The solvent was removed by rotary evaporation, the bla...

Embodiment 2

[0041] Example 2: Synthesis of 1-(4-iodobenzene)-imidazole

[0042]

[0043] 5.476 g (0.025 mol) of 4-iodoaniline and 12 ml of methanol were added to a 250 ml three-necked flask, and 4.2 ml of 40% glyoxal aqueous solution (containing 0.025 mol of glyoxal) was added, and the mixture was stirred at room temperature for 16 h. Then 2.675 g (0.050 mol) NH was added in sequence 4 Cl, 4 ml of 37% aqueous formaldehyde solution (containing 0.050 mol of formaldehyde), and 100 ml of methanol. After stirring and refluxing for 1h, 80% H was added dropwise in 30min 3 PO 4 3.5ml, and then continued to stir and reflux for 8h to stop the reaction.

[0044] The solvent was removed by rotary evaporation, the black residue was poured into 75 g of ice water, and the pH of the mixture was adjusted to 9 with 40% KOH solution. Extracted with dichloromethane (4×50ml), the organic phase was washed with water and saturated brine respectively, and anhydrous NaSO was added. 4 dried, filtered to r...

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Abstract

The invention discloses a zwitter-ion with an imidazole cation and malononitrile anion structure, a preparation method and application thereof. The zwitter-ion structure is characterized in that: a perssad which is connected onto a nitrogen atom in a molecule is an imidazole cation of an accepter electron group which is formed by alkyl groups, the other perssad which is connected onto the nitrogen atom is benzene ring or aromatic heterocycle, and one end of the benzene ring or aromatic heterocycle is connected with a malononitrile anion as a donor electron group. The zwitter-ion with the donor and accepter electron structures has good optical permeability, higher nonlinear value and good application prospect in the nonlinear optical material field.

Description

technical field [0001] The invention relates to the field of organic nonlinear optical materials and zwitterions, in particular to a zwitterion with imidazolium cation and malononitrile anion structures, a preparation method and application thereof. Background technique [0002] With the rapid development of communication technology and IT technology, people put forward higher requirements for nonlinear optical materials. Compared with inorganic nonlinear optical materials, organic materials have outstanding advantages such as designable structure, fast response, large optical nonlinear coefficient, and low price. Its disadvantages are low thermal stability and large absorption wavelength, which limit the practical application of organic nonlinear optical materials (J.Am.Chem.Soc., 2003, 125, 15651). [0003] Organic nonlinear optical materials are usually composed of large conjugated systems (Functional Organic Materials [M]. Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 200...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/56G02F1/361
Inventor 彭波王进韦玮高潮
Owner XI'AN INST OF OPTICS & FINE MECHANICS - CHINESE ACAD OF SCI
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