CN108017661A - 一种2,2′-联喹啉叠氮锌金属配合物及其制备方法和应用 - Google Patents
一种2,2′-联喹啉叠氮锌金属配合物及其制备方法和应用 Download PDFInfo
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- 239000011701 zinc Substances 0.000 title claims abstract description 24
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- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 12
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- 238000000034 method Methods 0.000 claims abstract description 8
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 claims abstract description 6
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- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 claims abstract description 5
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 claims abstract description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 4
- 238000002447 crystallographic data Methods 0.000 claims description 4
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- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical compound C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 abstract description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract description 6
- 238000009825 accumulation Methods 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000005284 excitation Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000003446 ligand Substances 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 150000001455 metallic ions Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
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- 238000012546 transfer Methods 0.000 description 2
- QFDUTPNKBRXHTC-UHFFFAOYSA-N zinc diazide Chemical compound [Zn++].[N-]=[N+]=[N-].[N-]=[N+]=[N-] QFDUTPNKBRXHTC-UHFFFAOYSA-N 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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Abstract
本发明公开了一种2,2'‑联喹啉叠氮锌金属配合物及其制备方法和应用。采用溶剂热合成方法，即反应物六水合硝酸锌、叠氮酸钠和2,2'‑联喹啉的摩尔比为1:2:1，2,2'‑联苯二甲酸适量，甲醇和水的混合液作为溶剂，反应升温至130～150℃，恒温3天，随后降至室温；过滤，乙醚洗涤滤饼，得到化学式为C18H12N8Zn的2,2'‑联喹啉叠氮锌配合物单晶。该配合物为单分子结构，通过氢键和π···π芳香环堆积构成三维超分子结构，且通过紫外光激发，在418nm处有强的荧光，可成为一种新的荧光发光材料，并可用于制作荧光发光器件。
Description
技术领域
本发明涉及金属有机配合物领域，特别是涉及一种2,2'-联喹啉叠氮锌金属配合物及其制备方法，和该配合物在发光材料方面的应用。
背景技术
金属有机配合物以其在气体储存、捕获，药物传输，生物成像及光、电、磁功能材料等方面卓越的特性，吸引了广大化学、材料学工作者的研究目光。该类化合物是以有机物为唯一或主要配体，通过配位键、其他分子间作用力与金属离子构筑成具有特定功能的金属有机材料。这种材料以有机配体配位形式多样性、灵活性及可修饰性，与金属离子配位能力的多变性相结合，赋予了不同于传统无机或有机材料的独特性质；同时，配位后材料的热学性能得到大大改善，扩大了应用范围。杂环芳香族有机化合物以其自身的刚性环和大的共轭体，往往具有极强的荧光性能和配位能力，与金属离子配位后，还可以通过改变配体分子轨道中的最高分子占有轨道(HOMO)能级和最低空轨道(LUMO)能级之间的能级差从而改变配体内的电荷转移，也可通过出现配体间或配体与金属离子之间的电荷转移，从而改变发射光的波长和强度，选择性地制备相关发光材料。为此，可以选择叠氮根与2,2'-联喹啉构成的混合配体，与某些过渡金属离子或稀土离子配位，合成出具有强发光能力的金属有机配合物。
发明内容
本发明的第一个目的是提供一种2,2'-联喹啉叠氮锌金属配合物。该配合物通过氢键和π···π芳香环堆积构成三维超分子结构。
本发明所涉及的2,2'-联喹啉叠氮锌金属配合物的化学式为(L1)·Zn(N3)2，其中L1为2,2'-联喹啉。该配合物的晶体属单斜晶系，空间群为C2/c，晶胞参数为： α＝90.00°，β＝118.290(2)°，γ＝90.00°。该配合物晶体最小不对称结构单元中包含一个Zn2+，1个L1配体、两个N3 -。中心离子Zn2+为四配位构型，分别与四个N原子配位，其中两个N原子来自于同一个L1配体，两个N原子来自于N3 -。Zn–N键长分别为和 N-Zn-N键角范围为80.73(10)-121.25(8)°。通过分子间弱的氢键和π···π芳香环堆积构成三维超分子结构。
本发明2,2'-联喹啉叠氮锌金属配合物的制备方法是：将六水合硝酸锌、叠氮酸钠、2,2'-联苯二甲酸、2,2'-联喹啉在甲醇和二次去离子水混合溶剂中经溶剂热反应制得无色块状晶体，其中六水合硝酸锌、叠氮酸钠和2,2'-联喹啉的摩尔比为1∶2∶1，2,2'-联苯二甲酸适量。反应介质为甲醇和二次去离子水。在130～150℃下恒温3天，随后降至室温，得到无色块状晶体，过滤，乙醚洗涤滤饼，得目标配合物。
所用原料2,2'-联苯二甲酸在此反应中仅作为酸性调节剂，不参与配位，使体系在酸性条件下反应。
所述的溶剂热反应指的是在内衬为聚四氟乙烯的不锈钢反应釜中以合适的溶剂为反应介质，利用电热恒温鼓风干燥箱控制温度，使得在通常情况下难溶或不容的物质溶解并结晶析出。
本发明的第二个目的在于提供一种2,2'-联喹啉叠氮锌金属配合物作为荧光材料。
附图说明
图1是本发明2,2'-联喹啉叠氮锌金属配合物的晶体结构图；
图2是本发明2,2'-联喹啉叠氮锌金属配合物的堆积结构图；
图3是本发明2,2'-联喹啉叠氮锌金属配合物的热重分析图
图4是本发明2,2'-联喹啉叠氮锌金属配合物的固体荧光光谱图。
具体实施方式
本发明2,2'-联喹啉叠氮锌金属配合物的化学式为(L1)·Zn(N3)2，其中L1为2,2'-联喹啉。
下面结合具体实施实例进一步阐述本发明。
实施例：将Zn(NO3)2·6H2O(29.7mg,0.1mmol)，2,2'-联喹啉(25.6mg,0.1mmol)，2,2'-联苯二酸(24.0mg,0.1mmol)和NaN3(13.2mg,0.2mmol)加入到12mL甲醇和二次去离子水(体积比为1:1)的混合溶剂中，在25mL内衬四氟乙烯的不锈钢容器中密封，加热至140℃并保持3天，然后缓慢冷却到室温。过滤，乙醚洗涤滤饼，在空气中干燥后，就得到无色块状晶体，基于Zn(NO3)2·6H2O计算产率约为61％。该物质不溶于水和其他有机溶剂。
本发明所述的2,2'-联喹啉叠氮锌金属配合物进一步表征，其过程如下：
1、所述的2,2'-联喹啉叠氮锌金属配合物的晶体结构测定
选取0.220mm×0.210mm×0.200mm大小的单晶，于293.2K下在Bruker Smart APEXII CCD单晶衍射仪上，以经石墨单色化的Mo-kα射线为入射辐射，扫描方式收集X-射线单晶衍射数据，采用最小二乘法精修晶胞参数，SHELXL-97直接法解析晶体结构，所有非氢原子用全矩阵最小二乘法进行各向异性精修。H原子位置理论模式计算确定。晶体衍射数据收集和结构精修的部分参数见表1，晶体结构如图1～2所示。
2、所述的2,2'-联喹啉叠氮锌金属配合物的热稳定性能研究
经洗涤、干燥处理后的配合物晶态样品在氮气保护下以10℃/min的速率从室温逐渐加热到800℃。热重分析曲线如图3所示，该化合物晶态材料热重分析曲线表现出一步失重过程，即失重发生在256℃～405℃，可见该材料具有非常良好的热稳定性，可以在较宽的温度范围内使用(图3所示)。
3、所述的2,2'-联喹啉叠氮锌金属配合物的固体荧光性能研究
经处理好的配合物晶态样品经充分研磨，室温下进行固体发光的测试。在310nm的紫外光激发下呈现出强的发光性质，发射峰位于418nm处(图4所示)。其在发光材料方面具有潜在的应用。
表1本发明2,2'-联喹啉叠氮锌金属配合物的晶体学数据
Claims (3)
1.2,2'-联喹啉叠氮锌金属配合物单晶，其特征在于该单晶结构采用Bruker SmartApex II CCD单晶衍射仪测定，以石墨单色化的Mokα射线，为入射辐射，扫描方式收集室温X-射线单晶衍射数据，最小二乘法精修晶胞参数，SHELXL-97直接法解得晶体数据：
2.一种如权利要求1所述的配合物单晶制备方法，其特征在于：将六水合硝酸锌、叠氮酸钠、2,2'-联苯二甲酸、2,2'-联喹啉在甲醇和二次去离子水混合溶剂中经溶剂热反应制得无色块状晶体；过滤，乙醚洗涤滤饼，得目标配合物单晶，其中2,2'-联苯二甲酸在该反应中不参与配位，仅作为酸性调节剂，使体系在酸性条件下反应。
3.一种如权利要求1所述的配合物单晶在制备荧光发光材料方面的应用。
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| CN112011064A (zh) * | 2020-08-04 | 2020-12-01 | 西安工程大学 | 基于联喹啉配体的铈-有机框架材料及其制备方法和应用 |
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| CN103965225A (zh) * | 2014-04-05 | 2014-08-06 | 安庆师范学院 | 8-氨基喹啉叠氮锌金属配合物及其制备方法和应用 |
| CN105001246A (zh) * | 2015-07-20 | 2015-10-28 | 安庆师范学院 | 8-氨基喹啉席夫碱叠氮锌金属配合物及其制备方法 |
| CN106243135A (zh) * | 2016-08-10 | 2016-12-21 | 安庆师范大学 | 一种叠氮酸锌‑8‑氨基喹啉席夫碱配合物及其制备方法 |
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