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Method for preparing platinum (II) and zinc (II) metal complex of benzothiazole ligand based on carbazole bridging structure and its application

A metal complex, benzothiazole technology, applied in zinc organic compounds, compounds containing elements of Group 8/9/10/18 of the periodic table, chemical instruments and methods, etc., can solve difficult processing, life, brightness and other directions. The problem of low luminescence chromaticity, easy crystallization, etc., achieves the effects of high yield, easy molecular design, and low cost

Active Publication Date: 2014-08-06
NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the organic small molecule luminescent material is formed into a film by vacuum evaporation, which has the disadvantages of being difficult to process and easy to crystallize; while the polymer luminescent material is formed into a film by spin coating, which has good film-forming properties and thermal stability. And mechanical properties, and the preparation process of the device is simple, the response speed is fast, and it can prepare large-area flexible display devices; but it is not as good as small organic molecules in terms of life, brightness, and luminous chromaticity.

Method used

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  • Method for preparing platinum (II) and zinc (II) metal complex of benzothiazole ligand based on carbazole bridging structure and its application
  • Method for preparing platinum (II) and zinc (II) metal complex of benzothiazole ligand based on carbazole bridging structure and its application
  • Method for preparing platinum (II) and zinc (II) metal complex of benzothiazole ligand based on carbazole bridging structure and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add 1-51.9mg (0.10mmol) of aldehyde, 26.2mg (0.21mmol, 2.1eq) of aminothiophenol, and 2.5mL of dimethyl sulfoxide to the sealed tube, and react at 180°C for 2-3h. The reacted system was extracted with dichloromethane (3mL×10), washed with water several times (20mL×10), the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated, and silica gel column chromatography (n-hexane:ethyl acetate= 20:1), to obtain 2-61.6mg of bright yellow solid, yield 88.0%.

[0035]1 H NMR (CDCl3, 300MHz, ppm): δ12.56 (s, 2H), 9.01-7.0 (m, 20H), 4.38 (t, J=7.0Hz, 2H) 1.97-1.92 (m, 2H), 1.25- 1.14(m, 10H), 0.88(t, J=5.7Hz, 3H).

[0036] IR (KBr tablet) cm -1 : v 3057, 2924, 2852, 1655, 1625, 1593, 1478, 1381, 1278, 1204, 983, 803, 759, 725.

[0037]

[0038] Add 2-42.0mg (0.060mmol) of thiazole, 14.5mg (0.066mmol, 1.1eq) of zinc acetate dihydrate, and 5.0mL of N,N-dimethylformamide into the sealed tube, and react at 100°C for 24h. Methanol was added...

Embodiment 2

[0041]

[0042] Add 4-63.1mg (0.10mmol) of aldehyde, 26.2mg (0.21mmol, 2.1eq) of aminothiophenol, and 2.5mL of dimethyl sulfoxide into the sealed tube, and react at 180°C for 2-3h. The reacted system was extracted with dichloromethane (3mL×10), washed with water several times (20mL×10), the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated, and silica gel column chromatography (n-hexane:ethyl acetate= 20:1), to obtain bright yellow solid 2-81.6mg, yield 86.0%

[0043] 1 H NMR (CDCl3, 300MHz, ppm): δ13.19(s, 2H), 8.36-7.38(m, 18H), 4.38(t, J=7.0Hz, 2H) 1.95(m, 2H), 1.92(s, 18H), 1.27(m, 10H), 0.86(t, J=5.7Hz, 3H).

[0044] IR (KBr tablet) cm -1 : v 2954, 2926, 28528, 1608, 1582, 1495, 1396, 1358, 1255, 1178, 1081, 806, 756, 725.

[0045]

[0046] Add 5-52.0mg (0.060mmol) of thiazole, 14.5mg (0.066mmol, 1.1eq) of zinc acetate dihydrate, and 5.0mL of N,N-dimethylformamide into the sealed tube, and react at 100°C for 24h. Methanol was add...

Embodiment 3

[0049] The ultraviolet absorption and fluorescence emission spectra of the thiazole ligands and corresponding metal complexes synthesized in the examples were measured in dichloromethane solution by using a Cary Eclipse fluorescence photometer (Varian, USA). (the compounds to be tested are all made into 10 -4 mol / L solution)

[0050] Carbazole-based ligand 2 and complex 3, as well as ligand 5 and complex 6, all have an obvious absorption peak at 300-320nm. This is the characteristic absorption peak of the benzene ring, which is π→π allowed by the spin * produced by the transition. At 350-450nm, 2 and 3 have a weak absorption peak, and 5 and 6 have a slightly stronger absorption peak. This is π→π for the C=N double bond * and n→π * The absorption peak generated by the transition is also spin-allowed. Compared with the ligands (2, 5), the characteristic absorption bands of complexes (3, 6) are red-shifted, indicating that the nitrogen atom participates in the coordination ...

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Abstract

The invention relates to a platinum (II) and zinc (II) metal complex of a benzothiazole ligand based on a carbazole bridging structure, its preparation method and its application, The platinum (II) and zinc (II) metal complex possesses a following structure shown in the description, wherein, M (II) is Zn (II) or Pt (II); R is H, OCH3, t-Bu or an aryl radical, and n is 1 to 100. The series metal complex possesses good photoluminescence performance and simple preparation method, and can be used for the aspects of organic electroluminescence materials.

Description

technical field [0001] The present invention relates to metal-organic complexes and their synthesis methods and applications, in particular to a series of platinum (II) and zinc (II) metal complexes based on carbazole bridged structure benzothiazole ligands, and their synthesis Methods and applications in the field of organic light emitting. technical background [0002] For the product: there is no report in the literature, and what is synthesized is a platinum (II) and zinc (II) metal complex based on a benzothiazole ligand with a carbazole bridge structure. [0003] For the method: the synthesis of the metal complex of the benzothiazole ligand based on the carbazole bridge structure is generally carried out in dimethyl sulfoxide, and the zinc and platinum complexes of the same kind of ligand are also carried out in dimethyl sulfoxide . [0004] Regarding the application: the synthesized platinum (II) and zinc (II) metal complexes based on the carbazole bridge structure ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/06C07F15/00C07D417/14C09K11/06
Inventor 姚小泉贾云超李可朱荔
Owner NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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