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Application of a tetranuclear copper [i] complex of o-picoline tetrazolium in stimuli-responsive luminescent color-changing materials

A technology of o-picoline tetrazolium and picoline tetrazolium, which is applied in the field of synthesis of new stimuli-responsive luminescent and color-changing materials, can solve the problems of difficult mining, shortage of raw material sources, and high cost of luminescent materials

Active Publication Date: 2019-06-18
JIANGXI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The transition metals of the fifth and sixth periods (except for a few metals of the first and second subgroups) are scarce in the earth's crust and are difficult to mine. Therefore, the cost of using luminescent materials based on such noble metal compounds is relatively high, and large-scale After application, it will also bring about tension in the source of raw materials
However, there are few literature reports on the application of nitrogen heterocyclic multidentate chelating ligands and organic bisphosphine ligands to construct luminescent and color-changing materials based on monovalent copper complexes, especially stimuli-responsive luminescent and color-changing materials based on monovalent copper complexes.
[0005] Using o-picoline tetrazole polydentate chelating ligand 5-[6-methyl-2-pyridyl]tetrazolium and organic bisphosphine auxiliary ligands to design and synthesize monovalent copper complexes in luminescence and color change in response to stimuli The application of materials has not yet been reported in the literature

Method used

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  • Application of a tetranuclear copper [i] complex of o-picoline tetrazolium in stimuli-responsive luminescent color-changing materials
  • Application of a tetranuclear copper [i] complex of o-picoline tetrazolium in stimuli-responsive luminescent color-changing materials
  • Application of a tetranuclear copper [i] complex of o-picoline tetrazolium in stimuli-responsive luminescent color-changing materials

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preparation example Construction

[0031]The present invention provides a method for preparing a stimuli-responsive luminescent color-changing material (this is the first preparation method) of a tetranuclear copper [I] complex of o-picoline tetrazolium, comprising the following steps:

[0032] Step 1: Under an argon atmosphere, [Cu[MeCN] with a molar ratio of 2:2:1 4 ][ClO 4 ], two [diphenylphosphine] methane [abbreviated as dppm], 5-[6-methyl-2-pyridyl] tetrazole [abbreviated o-mpytzH] in dichloromethane and stirred at room temperature for 2-4 hours, The first reaction mixture was obtained.

[0033] Step 2: adding sodium hydroxide in an equimolar amount to the 5-[6-methyl-2-pyridyl]tetrazolium ligand to the first reaction mixture, and continuing to stir and react at room temperature for 1-2 hours to obtain Second reaction mixture.

[0034] Step 3: Evaporate the solvent of the second reaction mixture to dryness, use dichloromethane-n-hexane mixed solvent for recrystallization, filter and recrystallize to ob...

Embodiment 1

[0045] Under an argon atmosphere, [Cu[MeCN] 4 ][ClO 4 ] (19.6mg, 0.060mmol), bis[diphenylphosphine]methane (23.1mg, 0.060mmol) and 5-[6-methyl-2-pyridyl]tetrazolium (4.8mg, 0.030mmol) in 10mL Stir and react at room temperature in dichloromethane for 3 hours, then add sodium hydroxide (1.2mg, 0.030mmol) to the reaction solution, continue to stir and react at room temperature for 1 hour, then evaporate the solvent to dryness with a rotary evaporator, and dichloromethane (1mL)-n-hexane (10mL) mixed solvent [volume ratio 1:10] for recrystallization. The colorless crystalline product obtained by recrystallization was filtered, washed 3-4 times with 10 mL of ether, and dried in vacuo to obtain a colorless solid product (27.7 mg, 0.012 mmol), with a yield of 80%.

[0046] Elemental analysis calculated value (C 114 h 100 Cl 2 Cu 4 N 10 o 8 P 8 ) as (%): C 59.25, H 4.36, N 6.06; Found: C 59.22, H 4.33, N 6.09.

[0047] X-ray single crystal diffraction: the crystal belongs to ...

Embodiment 2

[0050] Under argon atmosphere, copper perchlorate hexahydrate [Cu[ClO 4 ] 2 ·6H 2 O] (11.9 mg, 0.032 mmol) and excess copper powder (12.2 mg, 0.192 mmol) were stirred in 5 mL of acetonitrile for 30 minutes at room temperature, and then added into 10 mL of bis[diphenylphosphine] methane (24.6 mg, 0.064 mmol) Chloromethane solution, continue to stir and react for 1 hour, then add 5-[6-methyl-2-pyridyl]tetrazolium ligand (5.2mg, 0.032mmol), continue to stir and react for 2 hours at room temperature, and then add to the reaction solution Sodium hydroxide (1.28mg, 0.032mmol) was added to the mixture, and the stirring reaction at room temperature was continued for 1 hour. After filtration, the solvent was evaporated to dryness with a rotary evaporator, and the mixed solvent of dichloromethane (1mL)-n-hexane (10mL) [volume ratio 1:10] for recrystallization. The colorless crystalline product obtained by recrystallization was filtered, washed 3-4 times with 10 mL of ether, and dried...

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Abstract

The invention relates to an o-methyl pyridine tetrazolium tetranuclear copper [I] complex simulating response luminescent photochromic material which is characterized by being perchlorate.bi[5-[6-methyl-2-pyridyl] tetrazole]. tetra [bi[diphenylphosphine]methane] tetra copper [I] complex. The molecular formula thereof is C114H100Cl2Cu4N10O8P8. The invention also provides two methods for preparing the o-methyl pyridine tetrazolium tetranuclear copper [I] complex simulating response luminescent photochromic material which belongs to a new simulating response luminescent photochromic material andhas a wide application prospect.

Description

technical field [0001] The invention relates to the application of a tetranuclear copper [I] complex of o-picoline tetrazolium in a stimulus-responsive luminescent and color-changing material, and belongs to the technical field of synthesis of new stimulus-responsive luminescent and color-changing materials. Background technique [0002] Due to the influence of heavy atom effect and strong spin-orbit coupling, metal luminescent complexes can theoretically utilize all singlet and triplet energies, greatly improving the luminous efficiency. At present, the research on metallluminescent complexes mainly focuses on the fifth and sixth periods, especially transition metals of group VIII, such as ruthenium, osmium, iridium and platinum. The transition metals of the fifth and sixth periods (except for a few metals of the first and second subgroups) are scarce in the earth's crust and are difficult to mine. Therefore, the cost of using luminescent materials based on such noble metal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08C09K9/02
Inventor 何丽华陈景林王万曼温和瑞刘遂军廖金生
Owner JIANGXI UNIV OF SCI & TECH
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