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O-methyl pyridine tetrazolium tetranuclear copper [I] complex simulating response luminescent photochromic material and preparation method thereof

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

Active Publication Date: 2018-01-19
JIANGXI UNIV OF SCI & TECH
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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 complex stimuli-responsive luminescent color-changing materials And its preparation method, there is no literature public report yet at present

Method used

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  • O-methyl pyridine tetrazolium tetranuclear copper [I] complex simulating response luminescent photochromic material and preparation method thereof
  • O-methyl pyridine tetrazolium tetranuclear copper [I] complex simulating response luminescent photochromic material and preparation method thereof
  • O-methyl pyridine tetrazolium tetranuclear copper [I] complex simulating response luminescent photochromic material and preparation method thereof

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preparation example Construction

[0031]The present invention provides a preparation method of o-picoline tetrazolium tetranuclear copper [I] complex stimuli-responsive light-emitting color-changing material (this is the first preparation method), 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 obtain a...

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] (11.9mg, 0.032mmol) and excess copper powder (12.2mg, 0.192mmol) were reacted at room temperature in 5mL acetonitrile for 30 minutes with stirring, then added bis[diphenylphosphine]methane (24.6mg, 0.064mmol) in 10mL di 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 in ...

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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 a stimuli-responsive luminescent color-changing material and a preparation method thereof, belonging to the technical field of synthesis of new stimuli-responsive luminescent 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 compounds is relatively high, and large-scale After applica...

Claims

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Application Information

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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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