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Organic vapor luminescent off-color material of pyridine pyrazole copper [I] complex and preparation method thereof

A technology of copper pyridine pyrazole and organic steam, which is applied in the direction of color-changing fluorescent materials, copper organic compounds, chemical instruments and methods, etc., can solve the problems of tight source of raw materials, scarce content, difficulty in mining, etc., and achieve fast and efficient organic steam luminescence and color change The effect of nature

Active Publication Date: 2017-01-25
JIANGXI UNIV OF SCI & TECH
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Problems solved by technology

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 and are difficult to mine, so the cost of using luminescent complexes based on such noble metal elements is relatively high. Moreover, large-scale application will also bring about the problem of shortage of raw material sources.
However, there are few reports in the literature on the synthesis of monovalent copper dinuclear complex luminescent and color-changing materials using nitrogen heterocyclic multidentate chelating ligands and organic bisphosphine ligands, especially monovalent copper complex organic vapor luminescent color-changing materials.
[0005] Using pyridinepyrazole chelating ligand 5-trifluoromethyl-3-[2-pyridyl]pyrazole and organic bisphosphine ligand as auxiliary ligand, the technology of synthesizing monovalent copper complex organic vapor luminescent color-changing new materials , there is no public report in the literature

Method used

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  • Organic vapor luminescent off-color material of pyridine pyrazole copper [I] complex and preparation method thereof
  • Organic vapor luminescent off-color material of pyridine pyrazole copper [I] complex and preparation method thereof
  • Organic vapor luminescent off-color material of pyridine pyrazole copper [I] complex and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 在氩气气氛下,[Cu[MeCN] 4 ][ClO 4 ](21.6mg,0.066mmol)、1,2-双[二苯基膦]乙烷(26.4mg,0.066mmol)和5-三氟甲基-3-[2-吡啶基]吡唑(14.1mg,0.066mmol)在10mL二氯甲烷中常温搅拌反应3小时,后往该反应液中加入氢氧化钠(2.7mg,0.067mmol),常温下继续搅拌反应1小时,后用旋转蒸发仪将溶剂蒸干,用二氯甲烷(1mL)-石油醚(10mL)混合溶剂[体积比为1:10]进行重结晶。过滤重结晶得到的淡黄色晶态产物,用10mL乙醚洗涤3-4次,真空干燥后得到淡黄色固体产物——吡啶吡唑铜[I]配合物有机蒸汽发光变色材料(35.1mg,0.026mmol),产率为79%。

[0031] 元素分析计算值(C 70 h 58 Cu 2 f 6 N 6 P 4 )为(%):C 62.36,H 4.34,N 6.23;实测值:C62.39,H4.32,N 6.22.

[0032] X-射线单晶衍射:晶体属单斜晶系,P2 1 / c空间群,晶胞参数:a=21.691(4),b=14.919(3), β=91.694(4)°, Mr=1390.64,Z=4,Dc=1.409g cm -3 ,μ=0.851mm -1 ,GOF=1.043,晶体结构如 figure 1 shown.

[0033] 发光性能测试结果表明,该双核铜[I]配合物在常温固态时表现出良好的光致发光性能,最大峰值位于493nm,发光寿命为49μs,发光量子效率为71%,并对二氯甲烷蒸汽表现出快速高效的有机蒸汽发光变色性质,其在二氯甲烷蒸汽气氛和无二氯甲烷蒸汽气氛下的固态荧光发射光谱如 figure 2 shown.

Embodiment 2

[0035] Under argon atmosphere, copper perchlorate hexahydrate [Cu[ClO 4 ] 2 ·6H 2 O] (11.9mg, 0.032mmol) and excess copper powder (18.8mg, 0.296mmol) were stirred in 5mL acetonitrile for 30 minutes at room temperature, then added 1,2-bis[diphenylphosphine]ethane (25.6mg, 0.064 mmol) in 10 mL of dichloromethane solution, continue stirring for 1 hour, then add 5-trifluoromethyl-3-[2-pyridyl] pyrazole ligand (13.7 mg, 0.064 mmol), and continue stirring for 2 hours at room temperature , Add sodium hydroxide (2.6mg, 0.065mmol) to the reaction solution, and continue to stir the reaction at room temperature for 1 hour. ) mixed solvent [volume ratio of 1:10] for recrystallization. The light yellow crystalline product obtained by filtration and recrystallization was washed with 10 mL of ether for 3-4 times, and vacuum-dried to obtain a light yellow solid product——pyridine pyrazole copper [I] complex organic vapor luminescent color-changing material (32.4 mg, 0.024 mmol ), the yield...

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Abstract

The invention relates to a synthetic technology for an organic vapor luminescent off-color material, and particularly to an organic vapor luminescent off-color material of a dinuclear copper [I] complex containing pyridine pyrazole chelate ligands and a preparation method thereof. According to the invention, the pyridine pyrazole chelate ligands (5-trifluoromethyl-3-[2-pyridyl]pyrazol [pyfpzH for short]) and organic diphosphonic auxiliary ligands (1,2-bis[diphenylphosphine]ethane [dppe for short]) are used to prepare an organic vapor luminescent off-color material [Cu2[pyfpz]2[dppe]2] of a pyridine pyrazole dinuclear copper [I] complex. At normal temperature, the maximum value of the solid state luminescent wavelength of the pyridine pyrazole dinuclear copper [1] complex is 493nm, the luminescent lifetime is 49 microseconds, the luminescent quantum efficiency is 71%, and a fast efficient organic vapor luminescent off-color property to dichloromethane vapor is shown.

Description

technical field [0001] 本发明涉及有机蒸汽发光变色新材料合成技术,特别是一种含吡啶吡唑螯合配体的双核铜[I]配合物有机蒸汽发光变色材料及其制备方法。 Background technique [0002] 过渡金属发光配合物,因重原子效应和强自旋轨道耦合作用的影响,理论上可利用所有单重态和三重态能量,发光效率可大幅提升。目前,过渡金属发光配合物主要集中于第五、六周期,尤其是第VIII族过渡金属,而钌、锇、铱和铂占据了当前研究的中心位置。第五、六周期的过渡金属元素(除第一、二副族的少数几种金属元素外)在地壳中含量稀少,开采困难,因此基于此类贵金属元素的发光配合物的使用成本较高,而且大规模应用后还会带来原材料来源紧张的问题。另外,此类贵金属元素的配合物通常均有较大毒性,尤其是钌、锇、铼等贵金属配合物,因而,此类贵金属配合物的发光材料在大规模应用后还会带来环境污染及给生产和使用者带来直接或间接伤害。高使用成本及对环境不友好等缺陷使得它们的大规模推广应用受到了极大的限制,因此人们特别期望能在第五、六周期之外寻找到其它可替代的金属元素。 [0003] 比较第五、六周期的过渡金属元素,位于第四周期的金属铜元素,不仅资源丰富,廉价易得,而且对环境友好,光化学物理性质独特。此外,一价铜配合物还具有优良的室温可见磷光发射,发光可从紫外变到近红外,涵盖整个可见光区。资源丰富、价格低廉、发光性质优良和对环境友好等诸多优点使得一价铜发光配合物在发光器件、光学传感、智能材料、非线性光学材料、光伏器件、光催化等诸多领域表现出良好的应用前景。 [0004] 目前,在国内外文献中报道的一价铜发光配合物主要集中在一价铜金属簇合物和一价铜单核配合物。一价铜金属簇合物因为结构新颖,几何构型丰富,配位方式多样,光学性质独特等诸多优点,近年来越来越受到人们的极大关注。然而,选用氮杂环多齿螯合配体和有机双膦配体来合成一价铜双核配合物发光变色新材料的文献报道却很少,尤其是一价铜配合物有机蒸汽发光变色材料。 [0005] 应用吡啶吡唑螯合配体5-三氟甲基-3-[2-吡啶基]吡唑,有机双膦配体为辅助配体,合成一价铜配合物有机蒸汽发光变色新材料的技术,目前尚未见文献公开报道。 Contents of the invention [0006] 本发...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08C09K9/02
CPCC07F1/005C07F1/08C09K9/02C09K2211/1029C09K2211/1044C09K2211/188
Inventor 陈景林罗燕生何丽华廖金生刘遂军温和瑞
Owner JIANGXI UNIV OF SCI & TECH
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