Benzothiazole derivatives metal coordination polymer based on bridged bis-salicylaldehyde structure as well as manufacture method and application thereof

A technology of benzothiazoles and metal coordination, which is applied in the synthesis of metal coordination polymers, the synthesis of benzothiazole ligands, and the application fields of organic electroluminescent materials to achieve good thermal stability and process operation Simple, solubility-improving effect

Inactive Publication Date: 2010-11-24
NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Since the existing display technology cannot meet people's increasingly higher requirements for information display equipment, organic light-emitting devices (organic light-emitting devices, OLEDs) emerged as a new generation of flat panel display technology and gradually ente...

Method used

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  • Benzothiazole derivatives metal coordination polymer based on bridged bis-salicylaldehyde structure as well as manufacture method and application thereof
  • Benzothiazole derivatives metal coordination polymer based on bridged bis-salicylaldehyde structure as well as manufacture method and application thereof
  • Benzothiazole derivatives metal coordination polymer based on bridged bis-salicylaldehyde structure as well as manufacture method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Add 128mg (0.5mmol) of aldehyde, 131mg (1.05mmol, 2.1eq) of aminothiophenol, 2.5mL of DMSO into the sealed tube, and react at 185°C for 3h. After the reaction solution was cooled to room temperature, it was poured into 60mL water to form a white emulsion, and 5mL saturated saline was added to break the emulsion, CH 2 Cl 2 Extraction (15 mL x 3). The organic phases were combined, dried and concentrated, followed by column chromatography (petroleum ether / ethyl acetate=20:1) to obtain a pale yellow solid, which was the ligand, with a yield of 36%. 1 H NMR (CDCl 3 , 300MHz, ppm) δ: 12.45(s, 2H), 7.99(d, J=8.1Hz, 2H), 7.89(d, J=7.8Hz, 2H), 7.53~7.48(m, 4H), 7.41(t , J=7.5Hz, 2H), 7.24(d, J=8.4Hz, 2H), 7.07(d, J=8.4Hz, 2H), 4.01(s, 2H). 13 C NMR (CDCl 3 , 300MHz, ppm) δ: 169.4, 156.6, 152.0, 133.6, 132.7, 132.0, 128.4, 126.8, 125.7, 122.3, 121.7, 118.3, 116.8, 40.0.

[0034] IR (KBr tablet) cm -1 : v 3058, 2839, 1625, 1591, 1498, 1438, 1266, 1216, 996, 760....

Embodiment 2

[0036]

[0037] In the dichloromethane solution that dissolves the ligand of 0.05mmol (23.3mg), add dropwise the solution that has 0.055mmol (1.1eq, 7mg) Zn (OAc) 2 2H 2 2 mL of ethanol solution of O was added, and 0.1 mmol (2 eq, 14 μL) of triethylamine was added, and the reaction was stirred at room temperature for 24 h. Centrifuge after the reaction (5000rpm, 2min). The target compound was obtained by washing with ethanol and ether in sequence, and weighed after drying. The yield was 78%. IR (KBr tablet) cm -1 : v 3059, 1617, 1589, 1536, 1497, 1446, 1397, 1342, 1215, 998, 825, 756.

Embodiment 3

[0039]

[0040] Add 142mg (0.5mmol) of aldehyde, 131mg (1.05mmol, 2.1eq) of aminothiophenol, 2.5mL of DMSO into the sealed tube, and react at 185°C for 3h. After the reaction solution was cooled to room temperature, it was poured into 60mL water to form a white emulsion, and 5mL saturated saline was added to break the emulsion, CH 2 Cl 2 Extraction (15 mL x 3). The organic phases were combined, dried and concentrated, followed by column chromatography (petroleum ether / ethyl acetate=20:1) to obtain a light yellow solid, which was the ligand, with a yield of 46%. 1 H NMR (CDCl 3 , 300MHz, ppm) δ: 12.45(s, 2H), 8.01(d, J=8.1Hz, 2H), 7.89(d, J=8.1Hz, 2H), 7.64(d, J=8.1Hz, 2H), 7.52(t, J=7.4Hz, 2H), 7.41(t, J=7.7Hz, 2H), 7.30(dd, J=2.1, 10.8Hz, 2H), 7.07(d, J=8.7Hz, 2H), 1.81(s, 6H). 13 C NMR (CDCl 3, 300MHz, ppm) δ: 169.7, 156.2, 152.1, 141.6, 132.2, 126.8, 125.9, 125.6, 122.3, 122.2, 121.6, 117.9, 116.1, 41.9, 31.0.IR (KBr tablet) cm -1 : v 3448, 3052, 2967, 1625, 1594,...

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Abstract

The invention relates to a benzothiazole derivatives metal coordination polymer based on a bridged bis-salicylaldehyde structure, characterized by having the following structure which is shown in the specification, wherein linker is CH2 or C(CH3)2, R is H+, halogen base, phenyl or biphenyl, and M is Zn2+, Be2+ or Ca2+. The benzothiazole derivatives metal coordination polymer has favorable thermal stability, good fluorescent emission performance and simple preparation method. The coordination polymer of the type can be applied to the organic electroluminescent material aspect.

Description

technical field [0001] The present invention relates to metal-organic coordination polymers and their synthesis methods and applications, specifically the synthesis of benzothiazole ligands based on bridging bisalicylaldehyde structures, the synthesis of metal coordination polymers, and their use in Applications of electroluminescent materials. Background technique [0002] For the product: there is no report in the literature, and what is synthesized is a novel metal-organic coordination polymer based on the bridging bisalicylaldehyde structure. [0003] For the method: the synthesis of simple benzothiazole compounds is generally carried out in DMSO, and the same kind of complexes are generally carried out in alcohol solution. [0004] For application: the synthesized benzothiazole coordination polymer based on the structure of double salicylaldehyde is a new complex, and there is no report on its application as an organic electroluminescent material. [0005] Since the e...

Claims

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Application Information

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IPC IPC(8): C08G79/00C07F3/06C07F3/00C07F3/04C07D277/66C09K11/06
Inventor 姚小泉谷刘园屠慧
Owner NANJING UNIV OF AERONAUTICS & ASTRONAUTICS
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