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Aryl-substituted terpyridyl compounds, and preparation method and application thereof

A terpyridine and compound technology, which is applied in chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc. The effect of obtaining, simple reaction conditions and high yield

Inactive Publication Date: 2014-09-10
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It was first discovered by Stille et al. in the 1970s. The reaction is generally carried out under anhydrous and oxygen-free conditions, but the common organotin compounds in the experiment usually have high toxicity, thus limiting its application.
[0006] Ulmann coupling reaction is a reaction in which halogenated aromatic compounds and copper powder are co-heated to form biaryl compounds. This reaction was discovered by German chemist Ulmann in 1901, but most of the reactions require higher reaction temperatures.
Its application is limited due to its less mild reaction conditions

Method used

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  • Aryl-substituted terpyridyl compounds, and preparation method and application thereof
  • Aryl-substituted terpyridyl compounds, and preparation method and application thereof
  • Aryl-substituted terpyridyl compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of 2-bromophenyl-2,2':6'2"-terpyridine (II)

[0042]

[0043] In a round bottom flask containing 200 mL of methanol, 4-bromobenzaldehyde (2.0 g, 10.80 mmol), 2-acetylpyridine (4.4 g, 21.6 mmol), sodium hydroxide (0.44 g, 10.80 mmol) and 60mL of concentrated ammonia water (28%) was heated to 70°C and refluxed for 72h. After cooling to room temperature, a gray precipitate was obtained, which was filtered, and the filter cake was washed with water and methanol successively, and dried to obtain 2-bromophenyl-2,2':6'2"-terpyridine (3.8g, 89%). 1 H NMR (CDCl 3, 400MHz): δppm7.36-7.40(m, 3H), 7.48(t, J=8.0Hz, 2H), 7.67(d, J=8.0Hz, 2H), 7.74(d, J=8.0Hz, 2H) , 7.87-7.91(m, 2H), 8.00(d, J=8.0Hz, 2H), 8.68(d, J=8.0Hz, 2H), 8.73-8.76(m, 2H), 8.80(s, 2H).

Embodiment 2

[0044] Embodiment 2: the synthesis of compound shown in formula VI:

[0045]

[0046] Under nitrogen protection, II (388mg, 1mmol), potassium carbonate (552mg, 4.0mmol), tetrakis(triphenylphosphine) palladium (46mg, 0.04mmol), naphthalene borate (1.75g, 7.0mmol) were all added Into the Shrek tube, vacuum and replace with nitrogen three times. in N 2 Under a protective atmosphere, take 10 mL of ultrasonically degassed toluene: water = 4: 1 mixed solvent, inject it into a Shrek tube, then heat to reflux, and react for more than 20 h. TLC tracking shows that no raw material remains, and the reaction ends. Turn off the heating device, wait for the reaction system to cool down to room temperature, dilute with 20 mL of dichloromethane, wash with saturated brine three times, filter out insoluble matter, and collect the organic phase. After drying with anhydrous magnesium sulfate, the solvent was removed under reduced pressure to obtain a crude product. Using a mixed solvent of...

Embodiment 3

[0048] Embodiment 3: the synthesis of compound shown in formula VII:

[0049]

[0050] Under nitrogen protection, Compound VII was synthesized according to the method in Example 2. The product was a white solid with a yield of 85.0% and a melting point of 229-231°C. 1 H NMR (CDCl 3 , 400MHz): δppm7.01(d, J=2.0Hz, 2H), 7.34-7.38(m, 2H), 7.62(dd, J=2.0Hz, 2H), 7.7(d, J=8.0Hz, 2H) , 7.85-7.90(m, 2H), 7.95-8.03(m, 4H), 8.69(d, J=8.0Hz, 2H), 8.73-8.77(m, 3H), 8.80(s, 2H).TOF-MS (ES + )calcd.for C 28 h 21 N 3 O[M+1] + :462.2, found462.1.

[0051] The fluorescence lifetime of this product is 2.15ns, and the test method is the same as that in Example 2.

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Abstract

The invention provides aryl-substituted terpyridyl compounds, and a preparation method and application thereof. According to the method, 2-bromophenyl-2,2':6'2''-terpyridyl (II) and aryl borate used as raw materials react under reflux for 18-24 hours in an ultrasonic-degassed mixed solvent system composed of toluene and water in a ratio of 4:1 by using tetra(triphenylphosphine)palladium as a catalyst and potassium carbonate as an alkali. The compounds are suitable for developing and preparing organic luminescent materials and fluorescent materials.

Description

technical field [0001] The invention relates to an aryl-substituted terpyridine compound, a preparation method and its application as a photoelectric material in electroluminescence. technical background [0002] Terpyridine compounds have σ electron donating ability and π electron accepting ability, and can form stable complexes with various metals. In addition, terpyridine compounds have unique magnetic, photophysical and electrochemical properties compared with other compounds. Modification of the terpyridine structure can easily adjust the photophysical and electrochemical properties of the compound, so many novel functional materials can be designed by using these properties, which are used in optoelectronic devices, information storage, molecular switches, molecular machines and solar cells et al. (Synth. Met., 2004, 146, 11-15; J. Am. Chem. Soc., 2004, 126, 4958-4971; Chem. Mat., 2010, 22, 6384-6492). [0003] Terpyridine was first produced by Reported in Sythesis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/26C07D213/22C07D213/127C07D401/14C07D409/14C07D213/38C07D213/30C09K11/06H01L51/54
CPCC09K11/06C07D213/127C07D213/22C07D213/26C07D213/30C07D213/38C07D401/14C07D409/14C09K2211/1092C09K2211/1029H10K85/655H10K85/654H10K85/6572
Inventor 朱红军刘宇剑刘睿郭军朱晓林黄海金晓东李炜
Owner NANJING UNIV OF TECH
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