CN106588963B - 基于八羧基-杯[4]芳烃铽金属配合物及其制备方法 - Google Patents
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Abstract
一种基于八羧基‑杯[4]芳烃铽金属配合物及其制备方法，属于化学技术领域，配合物为下述化学式：[(CH3)2NH2][Tb2(HL)(H2O)7]·2H2O，其中HL为去七个质子的2,8,14,20‑四‑戊基‑4,6,10,12,16,18,22,24‑八‑羧基甲氧基‑杯[4]芳烃阴离子。配合物采用溶剂热方法制备。配合物的荧光测试研究表明该配合物具有强而稳定的绿色荧光，并且能够对有机小分子N,N’‑二甲基甲酰胺实现选择性高效探测，有望作为荧光材料在材料科学领域得到应用。
Description
技术领域
本发明属于化学技术领域，涉及一种八羧基取代杯[4]芳烃稀土金属配合物及其制备方法。
背景技术
探测有机小分子在生物技术及环境监测等领域具有非常重要的研究价值。但是大多数有机小分子具有结构基元相似，化学和物理性质相近的特性，此研究一直是化学工作者的挑战(W.J.Peveler,A.Roldan,N.Hollingsworth,M.J.Porter,I.P.Parkin,ACS Nano2016,10,1139-1146)。对于探测小分子，荧光测定提供了简单、灵敏、快速的技术支持(C.Wang,O.Volotskova,K.Lu,M.Ahmad,C.Sun,L.Xing,W.Lin,J.Am.Chem.Soc.2014,136,6171-6174)。基于镧系元素的金属有机框架具有特殊的荧光特性，在探测小分子方面的应用备受关注。
构建金属有机框架时所用配体的三重态能级与稀土离子能级是否匹配是Ln3+离子能否发光的主要影响因素(Y.Cui,B.Li,H.He,W.Zhou,B.Chen,G.Qian,Acc.Chem.Res.2016,49,483-493)。杯[4]芳烃及其衍生物具有多个芳环和碗状空腔，对于Ln3+金属有机框架的荧光发射是优异的天线配体(S.-T.Zhang,J.Yang,H.Wu,Y.-Y.Liu,J.-F.Ma,Chem.Eur.J.2015,21,15806–15819)。在镧系元素阳离子中，Tb3+在被激发时，能够实现天线配体到金属中心的能量传递，具有明显的绿光发射，是优异的金属荧光中心。由于合成步骤繁杂，八羧基取代的杯芳烃合成较少，对其配合物及性质的研究更为有限。基于荧光增强性质而成功探测有机小分子的研究未见过报导。
发明内容
本发明要解决的技术问题是公开一种八羧基功能化杯[4]芳烃(H8L)的铽金属配合物。
同时还公开了这种镧系金属配合物的制备方法。
金属配合物具有下述化学式，即：[(CH3)2NH2][Tb2(HL)(H2O)7]·2H2O，其中HL为去七个质子的八羧基-杯[4]芳烃配体阴离子。H8L为2,8,14,20-四-戊基-4,6,10,12,16,18,22,24-八-羧基甲氧基-杯[4]芳烃。
配合物晶体属于三斜晶系，空间群为P-1，晶胞参数为 α＝97.698(5)°，β＝92.368(5)°，γ＝98.312(4)°，基本结构为二维层状。
所述的八羧基-杯[4]芳烃铽金属配合物的制备方法，包括如下步骤：
(1)H8L配体的制备：母体l,3-双[(甲氧羰基)甲氧基]苯(L1)根据文献合成(H.Zhang,J.Yang,Y.-Y.Liu,S.Song,J.-F.Ma,Cryst.Growth Des.2016,16,3244-3255)。L1(10.0mmol)和己醛(10mmol)在30mL二氯甲烷中混合，冰浴搅拌下滴入BF3·OEt2(6mL)，然后室温搅拌十二小时。制得的固体即为L2，以二氯甲烷清洗后产率为58％。在L2中加入氢氧化钠(40mmol)、四氢呋喃(150mL)和水(150mL)。水浴除去溶剂，然后加入100mL水。使用HCl(1.0mol·L-1)将混合物的pH值调至1～2，得到H8L固体，此步产率为64％。
(2)八羧基-杯[4]芳烃铽金属配合物的合成：取H8L(0.1mmol)和TbCl3·6H2O(0.048mmol)，以体积比1：3的N,N’-二甲基甲酰胺(下面简写为DMF)和水为混合溶剂，放入到聚四氟乙烯反应釜中，在烘箱中加热到100℃恒温72小时，然后缓慢降到室温得到无色晶体。
晶体样品的荧光光谱数据显示此配合物具有强而稳定的荧光性能，并且能够对有机小分子DMF实现选择性高效探测，可以作为荧光材料在材料科学领域得到应用。
本发明八羧基-杯[4]芳烃铽配合物通过简单的溶剂热合成得到，具有制备方法简单、重复性强、产品性能稳定等特点。
附图说明
图1是配合物中金属铽的配位环境图；
图2是两个HL7-阴离子将Tb3+离子连接成的三明治状构型图；
图3是配合物的粉末衍射图；
图4是配合物的固态荧光发射谱图；
图5是配合物的固态荧光寿命衰减谱图；
图6是在配合物分散在不同有机小分子溶剂后的荧光发射对比图。
具体实施方式
金属配合物的合成：
H8L(27.0mg,0.1mmol)、TbCl3·6H2O(18.0mg,0.048mmol)、DMF(2mL)和水(6mL)混合，放入到15mL聚四氟乙烯反应釜中，放置在烘箱中加热到100℃恒温72小时，然后缓慢降到室温得到无色晶体，产率35％。
主要的红外吸收峰为：3750(s)，3525(s)，3325(m)，3249(m)，2929(w)，2856(m)，1711(m)，1583(w)，1507(w)，1454(w)，1427(w)，1375(m)，1331(m)，1298(w)，1257(m)，1188(m)，1119(w)，1071(m)，939(s)，908(s)，852(s)，775(s)，725(m)，680(m)，582(s)，510(s)，413(s)。
配合物的相关表征
(1)配合物的晶体结构测定
配合物的衍射数据在Oxford Diffraction Gemini R Ultra衍射仪上收集，293K，Mo Kα射线使用技术扫描进行校正。晶体结构是通过SHELEXL-97程序以直接法解出，用全矩阵最小二乘法SHELEXL-97进行精修。非氢原子的温度因子用各向异性进行修正。详细的晶体测定数据见表1；重要的键长和键角数据见表2；晶体结构见图1和图2。
发明的配合物其特征在于所述配合物晶体属于三斜晶系，空间群为P-1，晶胞参数为 α＝97.698(5)°，β＝92.368(5)°，γ＝98.312(4)°，单胞中包含两个独立的Tb3+离子，一个HL7-阴离子，七个配位水分子，一个游离的[H2N(CH3)2]+阳离子和两个游离水分子。Tb1离子与来自两个HL7-阴离子的八个氧原子和三个水分子配位；Tb2与来自三个HL7-阴离子的九个氧原子和四个水分子配位；每个HL7-阴离子与五个Tb3+配位。两个HL7-阴离子通过共享两个Tb1离子形成三明治型构筑单元。这些单元被Tb2阳离子进一步连接为独特的二维层状结构。
(2)配合物的XPRD相纯度表征(Rigaku Dmax 2000X-射线衍射器)。
通过粉末X-射线衍射来检测配合物晶体的相纯度(见图3)。
(3)配合物的荧光性质研究(FLSP920Edinburgh荧光光谱仪)。
在295nm激发时，配合物在488、543、584和623nm处有特征发射峰(图4)，峰位可归属为Tb3+阳离子的5D4→7FJ(J＝6-3)跃迁。对543nm最强峰位5D4→7F5跃迁的荧光衰减进行了测试和曲线拟合，荧光寿命为τ＝0.730ms(图5)。
(4)配合物的荧光探测小分子研究(FLSP920Edinburgh荧光光谱仪)。
先把配合物晶体研成粉末，然后取3mg分别与3mL有机小分子：氯仿、二氯甲烷、乙醇、乙腈、四氢呋喃、乙醚、环己烷、甲醇或DMF混合，剧烈搅拌后超声1分钟，制成悬浊液，在比色皿中测试荧光发射光谱。如图6，Tb3+配合物荧光强度受溶剂影响很大，对DMF具有卓越的荧光开启能力。说明配合物可以作为探测DMF的高效高选择性探测底物。
表1为配合物的主要晶体学数据
表2为配合物的主要键长和键角[°]*
对称代码：#1-x+1,-y+2,-z；#2x,y-1,z；#3x+1,y-1,z。
Claims (2)
1.一种八羧基-杯[4]芳烃铽金属配合物的制备方法，其特征在于：包括如下步骤：
八羧基-杯[4]芳烃铽金属配合物的合成：取TbCl3·6H2O 0.048 mmol 和2,8,14,20-四-戊基-4,6,10,12,16,18,22,24-八-羧基甲氧基-杯[4]芳烃H8L0.1 mmol 放入聚四氟乙烯反应釜中，以6 mL 水和2 mL N,N’-二甲基甲酰胺为混合溶剂，放置在烘箱中，加热到100℃恒温72 小时，然后缓慢降到室温即得；所述的H8L结构式为:
所述的八羧基-杯[4]芳烃铽金属配合物的化学式为[(CH3)2NH2][Tb2(HL)(H2O)7]·2H2O，它的晶体属于三斜晶系，空间群为P-1，晶胞参数为a = 11.6240(5) Å，b = 14.8640(9) Å，c = 22.1860(16) Å，α= 97.698(5)°，β= 92.368(5)°，γ= 98.312(4)°，V = 3751.6(4) Å3，基本结构是二维层状结构。
2.权利要求1所述的八羧基-杯[4]芳烃铽金属配合物作为探测DMF选择性探测底物的应用。
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| CN108586502B (zh) * | 2018-03-15 | 2019-12-27 | 中国科学院苏州生物医学工程技术研究所 | 双杯[4]芳烃衍生物的金属配合物及其合成方法和应用 |
| CN110577553B (zh) * | 2018-06-11 | 2021-09-21 | 天津师范大学 | 基于六核铽簇的三维多孔配合物的合成方法和应用 |
| CN109678895B (zh) * | 2018-12-04 | 2021-02-12 | 东北师范大学 | 巯基吡啶间苯二酚杯[4]芳烃锌配合物及制备方法和应用 |
| CN114907833B (zh) * | 2022-05-12 | 2023-09-15 | 中山大学 | 一种荧光检测探针及其在检测泼尼松龙中的应用 |
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| "Systematic Investigation of High-Sensitivity Luminescent Sensing for Polyoxometalates and Iron(III) by MOFs Assembled with a New Resorcin[4]arene-Functionalized Tetracarboxylate";Shuai-Tong Zhang et al.，;《Chem. Eur. J.》;20150911;第21卷(第44期);第15806-15819页 * |
| Four coordination polymers constructed by a novel octacarboxylate functionalized calix[4]arene ligand: syntheses, structures，and photoluminescence property;Hang Zhang et al.,;《CrystEngComm》;20140924;第16卷(第42期);第9939-9946页 * |
| Three resorcin[4]arene-based complexes with Cu(II)-exchange characteristics and fluorescence sensing of polyoxometalates in aqueous solutions;Wei Jiang et al.,;《CrystEngComm》;20140908;第16卷(第41期);第9638-9644页 * |
| 对叔丁基杯[ 6]芳烃稀土配合物的合成及荧光性能研究;钟平等;《中国稀土学报》;20090430;第27卷(第2期);第199-202页 * |
| 对叔丁基杯[ 8] 芳烃稀土配合物的合成、表征及荧光研究;燕来等;《光谱学与光谱分析》;20060531;第26卷(第5期);第928-932页 * |
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