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Pyridine pyrazole binuclear copper [i] complex luminescent material and preparation method

A pyridine pyrazole bis-luminescent material technology, applied in the direction of luminescent materials, copper organic compounds, chemical instruments and methods, etc., can solve the problems of few literature reports

Inactive Publication Date: 2016-11-30
JIANGXI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, there are few literature reports on the design and synthesis of monovalent copper dinuclear complex luminescent materials using polydentate nitrogen heterocyclic chelate ligands and organic bisphosphine ligands.
[0005] Application of pyridinepyrazole bidentate chelating ligands [3-[2-pyridyl]pyrazole, 5-tert-butyl-3-[2-pyridyl]pyrazole, 5-trifluoromethyl-3-[2 -pyridyl]pyrazole], organic bisphosphine ligand as auxiliary ligand, design and synthesis of monovalent copper complex luminescent new material and its preparation method, there is no public literature report yet

Method used

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  • Pyridine pyrazole binuclear copper [i] complex luminescent material and preparation method
  • Pyridine pyrazole binuclear copper [i] complex luminescent material and preparation method
  • Pyridine pyrazole binuclear copper [i] complex luminescent material and preparation method

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Experimental program
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Embodiment 1

[0047] Under argon atmosphere, equimolar [Cu[MeCN] 4 ][ClO 4 ] (186mg, 0.57mmol) and 1,4-bis[diphenylphosphine]butane (244mg, 0.57mmol) were stirred and reacted at room temperature in 20mL dichloromethane for 0.5 hours, and then added 3 -[2-pyridyl]pyrazole ligand (83mg, 0.57mmol), continue to stir the reaction at room temperature for 4 hours, then evaporate the solvent to dryness on a rotary evaporator, and dichloromethane (2mL)-ether (20mL) Mixed solvents [volume ratio 1:10] for recrystallization. The colorless crystalline product obtained by recrystallization was filtered, washed 3-4 times with 20 mL of ether, and a white solid product was obtained after vacuum drying, which was perchlorate·bis[3-[2-pyridyl]pyrazole]·di [μ-1,4-bis[diphenylphosphine]butane]copper[I] complex (309 mg, 0.21 mmol), yield 74%.

[0048] Elemental analysis calculated value (C 72 h 70 Cl 2 Cu 2 N 6 o 8 P 4 ) as (%): C 58.86, H 4.80, N 5.72; found values: C 58.82, H 4.85, N 5.75.

[0049] ...

Embodiment 2

[0055] Under argon atmosphere, copper perchlorate hexahydrate [Cu[ClO 4 ] 2 ·6H 2 O] (167mg, 0.45mmol) and excess copper powder (230mg, 3.62mmol) were stirred and reacted in 8mL acetonitrile for 20 minutes, then added 12mL of 1,4-bis[diphenylphosphine]butane (384mg, 0.90mmol) Dichloromethane solution, continue to stir and react for 1 hour, then add 3-[2-pyridyl]pyrazole ligand (131mg, 0.90mmol), continue to stir and react for 3 hours at room temperature, and evaporate the solvent on a rotary evaporator after filtration Dry and recrystallize with dichloromethane (2mL)-diethyl ether (20mL) mixed solvent [volume ratio 1:10]. The colorless crystalline product obtained by filtration and recrystallization was washed 3-4 times with 25 mL of ether, and a white solid product was obtained after vacuum drying, which was perchlorate bis[3-[2-pyridyl]pyrazole] bis[ μ-1,4-bis[diphenylphosphine]butane]copper[I] complex (456mg, 0.31mmol), the yield was 69%.

[0056] Analysis and character...

Embodiment 3

[0059] Under argon atmosphere, equimolar [Cu[MeCN] 4 ][ClO 4 ] (193mg, 0.59mmol) and 1,4-bis[diphenylphosphine]butane (252mg, 0.59mmol) were stirred and reacted at room temperature in 20mL dichloromethane solvent for 0.5 hours, and then added to the colorless transparent reaction solution 5-tert-butyl-3-[2-pyridyl]pyrazole ligand (119mg, 0.59mmol), continued to stir and react at room temperature for 4 hours, then evaporated the solvent to dryness on a rotary evaporator, and dichloromethane ( 2mL)-diethyl ether (20mL) mixed solvent [volume ratio 1:10] for recrystallization. The colorless crystalline product obtained by filtration and recrystallization was washed with 15 mL of ether for 3-4 times, and a white solid product was obtained after vacuum drying, which was perchlorate di[5-tert-butyl-3-[2-pyridyl ]pyrazole]·bis[μ-1,4-bis[diphenylphosphine]butane]copper[I] complex (332 mg, 0.21 mmol), yield 71%.

[0060] Elemental analysis calculated value (C 80 h 86 Cl 2 Cu 2 N ...

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Abstract

The invention relates to a dinuclear copper [1] complex luminescent material containing pyridine pyrazole chelating ligand and a preparation method thereof. By the application of the functional pyridine pyrazole two-tooth chelating ligand (3-[2-pyridyl] pyrazole [pypzH for short] or 5-tertiary butyl-3-[2-pyridyl] pyrazole [pybpzH for short] or 5-trifluoromethyl-3-[2-pyridyl] pyrazole [pyfpzH for short] and organic double phosphine auxiliary ligand (1,4-double[diphenylphosphine] butane [dppb for short]), a kind of pyridine pyrazole dinuclear copper [1] complex luminescent material [Cu2[pypzH]2[u-dppb]2][ClO4]2,[Cu2 [pybpzH]2[u-dppb]2][ClO4]2 and [Cu2[pyfpzH]2[u-dppb]2][ClO4]2 is prepared. The solid state luminescence property of the luminescent material can be regulated and controlled through the change of the substituent group on the pyridine and pyrazole ring, the maximum values of the solid state luminescence wave length of the luminescent material are 500 nm, 505 nm and 494 nm, the solid state luminescence life of the luminescent material is 48 us, 19 us and 36 us, and the solid state luminescence quantum efficiency of the luminescent material is 74%, 6% and 85%.

Description

technical field [0001] The invention relates to synthesis technology of new luminescent materials, in particular to a kind of dinuclear copper [I] complex luminescent materials containing pyridine pyrazole chelating ligands and a preparation method thereof. Background technique [0002] Due to the heavy atom effect and strong spin-orbit coupling, the luminescent complexes based on transition metals can theoretically utilize the energy from all singlet and triplet states, and the luminous efficiency can be greatly and effectively improved. At present, the metal centers of transition metal luminescent complexes are mainly concentrated in the fifth and sixth periods, especially the transition metals of group VIII, while ruthenium, osmium, iridium and platinum occupy the central positions of current research. Since the transition metal elements of the fifth and sixth periods (except for a few metal elements of the first and second subgroups) are scarce in the earth's crust, mini...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08C07F9/6558C09K11/06
Inventor 陈景林郭宗浩何丽华刘遂军温和瑞
Owner JIANGXI UNIV OF SCI & TECH
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