CN104277074A - 四苯乙烯锰配合物及在镉离子和锌离子荧光探针方面的应用 - Google Patents
四苯乙烯锰配合物及在镉离子和锌离子荧光探针方面的应用 Download PDFInfo
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- KJZKEHGAGNPQOW-UHFFFAOYSA-N manganese 1,2,2-triphenylethenylbenzene Chemical compound [Mn].C1(=CC=CC=C1)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 KJZKEHGAGNPQOW-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000007850 fluorescent dye Substances 0.000 title abstract 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 title description 2
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 title description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 239000011572 manganese Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 4
- CQCXGBMHIXQKCC-UHFFFAOYSA-N N1N=NC=C1.C1(=CC=CC=C1)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N1N=NC=C1.C1(=CC=CC=C1)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 CQCXGBMHIXQKCC-UHFFFAOYSA-N 0.000 claims description 11
- 239000013078 crystal Substances 0.000 claims description 11
- 239000000523 sample Substances 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000005260 alpha ray Effects 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- QZZGHWFLUFTTOI-UHFFFAOYSA-N 1-[4-[1,2,2-tris[4-(1,2,4-triazol-1-yl)phenyl]ethenyl]phenyl]-1,2,4-triazole Chemical group C1=NN(C=N1)C1=CC=C(C=C1)C(=C(C1=CC=C(C=C1)N1C=NC=N1)C1=CC=C(C=C1)N1C=NC=N1)C1=CC=C(C=C1)N1C=NC=N1 QZZGHWFLUFTTOI-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 12
- 239000011701 zinc Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 0 CC(C1)*=C([*@](**)C=[*+]C)[C@@]2C1=C2 Chemical compound CC(C1)*=C([*@](**)C=[*+]C)[C@@]2C1=C2 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开了一种四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3( 1 )(TTPE=1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)的制备方法及作为Cd2+和Zn2+离子荧光探针。它是采用“一步法”,即MnCl2·4H2O和1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯常温搅拌来制备该配合物。
Description
本发明得到国家自然科学基金面上项目(21471113)资助。
技术领域
本发明属于无机合成技术领域,涉及四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)单晶的制备方法及作为Cd2+和Zn2+离子荧光探针的应用。
背景技术
1,2,4-三唑及其衍生物兼有吡唑和咪唑的配位特点,是配位能力较强的桥连配体,目前已合成并表征了大量的单核、多核和多维化合物。这些配体能够以1,2位上的氮原子与金属离子配位形成N1,N2-桥连模式,对于4位未取代的1,2,4-三唑衍生物能通过2,4位上的氮原子形成N2,N4-桥连模式,这种N2,N4-桥连模式同金属酶中咪唑的N1,N3-桥连模式类似。对于三唑类化合物的特殊用途还表现在分子器件化的设计上,合成具有不同维数的金属配合物乃是完成器件化至关重要的一步。
四苯乙烯三唑类衍生物是一类性能优良的光电材料,本发明选用MnCl2·4H2O与四苯乙烯三唑自组装,得到二维(4,4)拓扑结构的层状结构配合物。荧光测试结果表明,该配合物可以作为Cd2+和Zn2+离子荧光探针。迄今为止,该配合物是首例基于三唑衍生物的Cd2+和Zn2+离子荧光探针。
发明内容
本发明的另一个目的在于提供一种四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)单晶及其制备方法。
为此本发明人提供了如下的技术方案:
四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)单晶的结构基元如图1所示:
本发明进一步公开了四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)单晶,其特征在于该单晶结构采用APEX II CCD 单晶衍射仪,使用经过石墨单色化的Mokα射线(λ= 0.71073 Å)为入射辐射,以ω-2θ扫描方式收集衍射点,经过最小二乘法修正得到晶胞参数,从差值傅立叶电子密度图利用SHELXL-97直接法解得单晶数据:
本发明所述四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)单晶的制备方法,其特征在采用“一步法”,在CHCl3、CH3OH和H2O中,将MnCl2·4H2O、四苯乙烯三唑配体常温搅拌半小时后过滤,滤液缓慢挥发,两周后得到适合X-射线单晶衍射的黄色块状晶体。其中CHCl3、CH3OH和H2O的体积比为1:8:1,MnCl2·4H2O、四苯乙烯三唑配体的摩尔比为4:1;
本发明更加详细的制备方法如下:
一种四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)单晶的制备方法其特征在于,在CHCl3、CH3OH和H2O中,采用“一步法”,将MnCl2·4H2O和四苯乙烯三唑配体常温搅拌以制备该配化合物;
本发明所述的溶剂为混合溶剂,CHCl3、CH3OH和H2O。
其中MnCl2·4H2O、四苯乙烯三唑配体的摩尔比为4:1;
本发明进一步公开了四苯乙烯锰配合物1在制备荧光材料方面的应用。所述的荧光材料指的是该化合物作为Cd2+和Zn2+离子荧光探针的应用。
本发明公开的四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)单晶所具有的优点和特点在于:
(1)反应操作简便易行。
(2)反应收率高,所得产品的纯度高。
(3)本发明所制备[Mn(TTPE)Cl2]·4CHCl3 (1)
(TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯)生产成本低,利润空间大,更适合大规模的工业化生产。
附图说明
图1:配合物1的晶体结构基元图;
图2:配合物1的二维(4,4)层状结构图;
图3:不同离子对配合物1荧光强度的影响。
具体实施方式
下面结合实施例对本发明做进一步的说明,实施例仅为解释性的,决不意味着它以任何方式限制本发明的范围。所有的原料例如:四苯乙烯等都是从国内外的化学试剂公司进行购买,没有经过继续提纯而是直接使用的。产物的熔点是在型号为X4 Micro的熔点仪上进行测量的。
实施例1
MnCl2·4H2O、四苯乙烯三唑的摩尔比为4:1;
将MnCl2·4H2O (0.0198g,
0.1mmol)和TTPE (0.0150g, 0.025mmol)在CHCl3/CH3OH/H2O
(15 mL, V:V:V = 3:10:2)的混合溶剂中搅拌30分钟后过滤得到棕黄色的滤液。室温下滤液缓慢挥发两周,得到适合X-射线单晶衍射分析的黄色块状晶体。产率:45% (基于TTPE计算)。元素分析(C38H28Cl14MnN12):C,37.91;H,2.34;N,13.96。实测值:C,37.69;H,2.42;N,13.77。
实施例2
晶体结构测定采用APEX II CCD单晶衍射仪,使用经过石墨单色化的Mokα射线(λ= 0.71073 Å)为入射辐射,以ω-2θ 扫描方式收集衍射点,经过最小二乘法修正得到晶胞参数,从差值傅立叶电子密度图利用软件解出晶体结构,并经洛仑兹和极化效应修正。所有的H原子由差值傅立叶合成并经理想位置计算确定。详细的晶体测定数据见表1。结构基元见图1,二维(4,4)拓扑层状结构见图2。
表1 配合物1的晶体学数据
实施例3
其中MnCl2·4H2O和四苯乙烯三唑的摩尔比为4:1;
我们还尝试过其他比例,比如MnCl2·4H2O和四苯乙烯三唑的摩尔比为1:1,则无论搅拌时间的长短,都得不到晶态化合物。因此MnCl2·4H2O和四苯乙烯三唑的摩尔比为4:1是最佳反应配比。
实施例4
Cd2+和Zn2+离子荧光探针
如图3所示,当在配合物1的DMSO溶液中加入1-3倍当量的Cd2+或Zn2+离子,520 nm出现的最大发射峰强是不加Cd2+或Zn2+离子的四倍或二倍。加入1-3倍当量的Ni2+、Co2+、Ca2+和Mg2+离子加入到该体系中,其发射光强相对于1来说有不同程度减弱。以上实验结果表明,1的发光强度表现出对Cd2+和Zn2+离子的高度选择性,因此可作为Cd2+和Zn2+离子荧光探针。据我们所知,这是是第一例基于三唑衍射物的Cd2+和Zn2+离子荧光探针。
在详细说明的较佳实施例之后,熟悉该项技术人士可清楚地了解,在不脱离上述申请专利范围与精神下可进行各种变化与修改,凡依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰,均属于本发明技术方案的范围。且本发明亦不受说明书中所举实例实施方式的限制。
Claims (4)
1.四苯乙烯锰配合物[Mn(TTPE)Cl2]·4CHCl3 (1)的结构基元如下:
TTPE = 1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯。
2.权利要求1所述四苯乙烯锰配合物1单晶,其特征在于该单晶结构采用APEX II CCD单晶衍射仪,使用经过石墨单色化的Mokα射线(λ= 0.71073 Å)为入射辐射,以ω-2θ扫描方式收集衍射点,经过最小二乘法修正得到晶胞参数,从差值傅立叶电子密度图利用软件解出单晶数据:
。
3.权利要求1所述四苯乙烯锰配合物的制备方法,其特征在于:在混合溶剂中采用“一步法”,即MnCl2·4H2O和1,1,2,2-四[4-(1H-1,2,4-三氮唑-1-基)苯基]乙烯常温搅拌来制备该配合物;所述的溶剂为混合溶剂,CHCl3、CH3OH和H2O;MnCl2·4H2O:四苯乙烯三唑配体的摩尔比为4:1;
。
4.权利要求1所述所述四苯乙烯锰配合物在作为Cd2+和Zn2+离子荧光探针方面的应用。
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CN104592272A (zh) * | 2015-02-26 | 2015-05-06 | 天津师范大学 | 具有潜在荧光材料的四苯乙烯四三唑溴化镉配合物及其制备方法 |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103772304A (zh) * | 2014-01-14 | 2014-05-07 | 天津师范大学 | 四苯乙烯化合物及其制备方法与应用 |
-
2014
- 2014-09-25 CN CN201410495883.8A patent/CN104277074B/zh not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103772304A (zh) * | 2014-01-14 | 2014-05-07 | 天津师范大学 | 四苯乙烯化合物及其制备方法与应用 |
Non-Patent Citations (1)
Title |
---|
HONG-LING ZHANG等,: "Syntheses and characterizations of two-dimensional polymers based on tetraimidazole tetraphenylethylene ligand with aggregation-induced emission property", 《INORGANIC CHEMISTRY COMMUNICATIONS》, 29 June 2013 (2013-06-29), pages 208 - 212, XP 028749974, DOI: doi:10.1016/j.inoche.2013.06.035 * |
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