CN113173919B - 一种两亲性双苯并咪唑衍生物及其超分子传感器的制备与应用 - Google Patents
一种两亲性双苯并咪唑衍生物及其超分子传感器的制备与应用 Download PDFInfo
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Abstract
本发明提供了一种两亲型的双苯并咪唑衍生物BBI,以两亲型双苯并咪唑衍生物BBI为客体,水溶性柱[5]芳烃衍生物WP5为主体,在水溶液中按照1:2的摩尔比自组装形成稳定的超分子传感器BBI‑WP5,该超分子传感器BBI‑WP5中加入常见的14种金属离子的水溶液时,发现只有加入Pb2+时才能使超分子传感器BBI‑WP5的荧光打开,并且发射出明亮的蓝色荧光,最低检测限为5.7×10‑8M,实现了纯水相中对Pb2+的专一选择性识别。
Description
技术领域
本发明涉及一种两亲性双苯并咪唑衍生物及其合成方法;本发明还涉及一种基于两亲性双苯并咪唑衍生的超分子传感器;本发明同时还涉及该超分子传感器在专一选择性识别Pb2+的应用,属于化合物合成和离子检测技术领域。
背景技术
柱芳烃是由对苯二酚或对苯二酚醚通过亚甲基桥在苯环的对位连接而成的一类新型环状低聚物,是一类新型的大环主体分子。柱芳烃识别客体分子的多样性(客体分子可以是中性的或者离子型的)和实现客体识别时溶剂的广泛兼容性(不仅可以在有机相中进行主客体络合,也可实现在水相中的选择性识别)赋予了其在构筑超分子材料方面极大的优势,使其在超分子聚合物、跨膜通道、超分子自组装、超分子有机框架材料、超分子探针和药物传递方面有着广泛的应用。
苯并咪唑及其衍生物是一类重要的杂环化合物。近年来,对含苯并咪唑配合物的研究一直都是热点。其主要应用在生物学、药理学、光电材料等领域,并常常被用来作为研究金属酶的模型配体,在医药、化学化工和生物学等领域也具有重要应用价值。苯并咪唑及其衍生物作为氮杂环化合物具有特殊的生理活性,如抗病毒、治疗和预防骨炎/肝炎、抑制真菌等病毒的生长。
日常生活中铅是非常常见的重金属元素,早些年因为汽油中用铅作为防爆剂使得尾气排放产生了大量的铅,近年来随着无铅汽油的普及尾气中的铅排放己经很少,主要的铅污染源是矿石行业,蓄电池行业,颜料染色行业,铅的生物毒性体现在对肾的损伤以及血液供给的不足同时过量的铅还会引起神经机能的紊乱,铅进入人体难以代谢会不断蓄积如果饮用水中铅含量不达标会引起蓄积性慢性铅中毒。因此,建立准确,快速的Pb2+检测方法在生物医学方面,环境质量检测等方面具有重要的意义。
发明内容
本发明的目的提供一种两亲性双苯并咪唑衍生物及其合成方法;
本发明的另一个目的是提供了一种基于两亲性双苯并咪唑衍生物的超分子传感器;
本发明还有个目的是提供基于两亲性双苯并咪唑衍生物的超分子传感器专一选择性识别Pb2+中的应用。
一、两亲性双苯并咪唑衍生物BBI及合成
一种两亲型的双苯并咪唑衍生物BBI,其结构式为:
本发明一种两亲型双苯并咪唑衍生物BBI的合成方法,包括以下工艺步骤:
(1)2,2’-双苯并咪唑的合成:将二水合草酸和邻苯二胺充分研磨混合均匀,加入多聚磷酸和乙二醇搅拌混合,在N2保护下,逐渐升温至沸腾,回流1~1.5 h,停止加热,待反应物冷却至60~80℃,倾入蒸馏水中,充分搅拌,静置,抽滤,滤饼转入20%的乙醇溶液中,搅拌分散后再抽滤,即得粗产物,粗产物转入醋酸中,加热至沸腾,使之全部溶解完全后冷却至室温,得金黄色蓬松的针状晶体,过滤,真空干燥,得2,2’-双苯并咪唑。其中,二水合草酸和邻苯二胺的摩尔比为1:2~1:2.5;二水合草酸与多聚磷酸的摩尔比为1:2~1:2.5。
(2)1,1’-二溴己基-2,2’-双联苯并咪唑的合成:以DMF为溶剂,KOH粉末为催化剂,将2,2’-联苯并咪唑与1,6-二溴己烷在0~5℃下搅拌反应4~6h,用H2O和二氯甲烷进行萃取,下层滤液用无水硫酸钠干燥并蒸发,得到粗产物,然后通过柱色谱分离获得黄色固体粉末1,1’-二溴己基-2,2’-双苯并咪唑。其中,2,2’-联苯并咪唑与1,6-二溴己烷的摩尔比为1:10~1:10.5;2,2’-联苯并咪唑与KOH粉末的摩尔比为1:4~1:4.5。
(3)两亲性双苯并咪唑衍生物的合成:用乙腈做溶剂,将1,1’-二溴己基-2,2’-双苯并咪唑与1-甲基咪唑在55~60℃下搅拌反应45~50小时,反应结束后进行蒸发浓缩,得到黄色固体即为目标产物两亲性双苯并咪唑衍生物BBI。其中,1,1’-二溴己基-2,2’-联苯并咪唑与1-甲基咪唑的摩尔比为1:5~1:5.5。
BBI的核磁氢谱和碳谱图见图1和图2。
二、基于两亲性双苯并咪唑衍生物的超分子传感器
本发明基于两亲性双苯并咪唑衍生物的超分子传感器,是以两亲型双苯并咪唑衍生物BBI为客体,水溶性柱[5]芳烃衍生物WP5为主体,在水溶液中按照1:2的摩尔比自组装形成稳定的超分子传感器BBI-WP5。
水溶性柱[5]芳烃衍生物WP5的结构式如下:
水溶性柱[5]芳烃衍生物WP5的合成见参考文献:Y. Ma, X. Ji, F. Xiang, X.Chi, C. Han, J. He, Z. Abliz, W. Chen and F. Huang, Chem.Commun., 2011, 47,12340-12342.
WP5的核磁氢谱图见3。
三、超分子传感器BBI-WP5对Pb2+的检测
1、BBI-WP5对Pb2+的专一性识别
配置浓度为1×10-5mol/L的BBI-WP5的水溶液,移取一系列体积为2mL的BBI-WP5水溶液于荧光比色皿,向BBI-WP5中分别加入5倍当量的不同金属离子水溶液(Ag+, Al3+, Ba2 +, Ca2+, Cd2+, Co2+, Cr3+, Cu2+,Fe3+,Hg2+,Mg2+,Ni2+,Pb2+,Zn2+),离子的浓度为0.1mol/L。观察BBI-WP5对各种金属离子的荧光响应。由图4可知,通过荧光光谱发现,只有Pb2+能使BBI-WP5的荧光打开,并且发射出明亮的蓝色荧光,在相同条件下,其它金属离子的加入对BBI-WP5的荧光没有明显影响。以上结果说明BBI-WP5能单一选择性荧光识别Pb2+。
2、BBI-WP5对Pb2+的滴定实验
用荧光比色皿移取一份体积为2mL的BBI-WP5水溶液,向其中逐渐加入Pb2+水溶液(浓度为0.01mol/L),用荧光分光光度计测定该超分子传感器BBI-WP5荧光强度的变化。由图5可知,随着Pb2+的逐渐加入,BBI-WP5的荧光逐渐增强。经3σ法计算可知(图6),BBI-WP5对Pb2+的荧光检测限为5.7×10–8M,说明BBI-WP5对Pb2+有较高的灵敏度。
综上所述,本发明首先合成了一种两亲型双苯并咪唑衍生物BBI,该双苯并咪唑衍生物在水溶液中与水溶性柱[5]芳烃衍生物WP5自组装形成超分子传感器BBI-WP5,该超分子传感器BBI-WP5在纯水相中可以对Pb2+单一选择性荧光识别,选择性强,灵敏度高。
附图说明
图1为BBI的核磁氢谱图;
图2为BBI的核磁碳谱图;
图3为WP5核磁氢谱图;
图4为BBI-WP5对各种金属离子的荧光光谱图;
图5为BBI-WP5对Pb2+的荧光滴定实验;
图6为BBI-WP5的荧光滴定拟合曲线。
具体实施方式
下面通过具体实施例对本发明客体分子两亲性双苯并咪唑衍生物BBI及基于两亲性双苯并咪唑衍生物的超分子传感器BBI-WP5的制备以及应用做进一步说明。
实施例1、两亲性双苯并咪唑衍生物BBI的合成
(1)2,2’-联苯并咪唑的合成:称取4.2g(33mmol)二水合草酸和7.2g(67mmol)邻苯二胺于研钵中,充分研磨混合均匀,转入烧瓶中,加入12mL(75mmol)多聚磷酸和20mL乙二醇,搅拌混合。N2保护下,逐渐升温至沸腾,回流1h。停止加热,待反应物冷却至70℃,倾入500mL水中,充分搅拌,静置,抽滤。滤饼转入20%的乙醇溶液中,搅拌分散后再抽滤,此过程再重复一次,即得粗产物。粗产物转入醋酸(1g/80mL)中,加热至沸腾,使之全部溶解完全后冷却至室温,得大量金黄色蓬松的针状晶体,过滤,真空干燥至恒重,得2,2’-双苯并咪唑,产率85%。
(2)1,1’-二溴己基-2,2’-联苯并咪唑的合成:以DMF为溶剂,固体KOH(20mmol,1.12g)粉末为催化剂,将2, 2’-联苯并咪唑(5mmol,1.17g)与1,6-二溴己烷(50mmol,12.20g)在0℃下搅拌反应5小时,用H2O和二氯甲烷进行萃取。下层滤液用无水硫酸钠干燥并蒸发,得到粗产物。然后通过柱色谱分离获得黄色固体粉末1,1’-二溴己基-2,2’-联苯并咪唑,产率为58%。
(3)两亲性双苯并咪唑衍生物的合成:用乙腈做溶剂,1,1’-二溴己基-2,2’-联苯并咪唑(2mmol,1.16g )与1-甲基咪唑(10mmol,0.82g )在55~60℃下搅拌反应48小时,反应结束后进行蒸发浓缩,得到黄色固体产物即为目标产物BBI,产率为54%。
两亲性双苯并咪唑衍生物BBI的合成路线如下:
水溶性柱[5]芳烃衍生物WP5的合成见参考文献:Y. Ma, X. Ji, F. Xiang, X.Chi, C. Han, J. He, Z. Abliz, W. Chen and F. Huang, Chem.Commun., 2011, 47,12340-12342.
实施例2、基于权利两亲性双苯并咪唑衍生物的超分子传感器
以两亲型双苯并咪唑衍生物BBI为客体,水溶性柱[5]芳烃衍生物WP5为主体,在水溶液中按照1:2摩尔比自组装成稳定超分子传感器BBI-WP5。
实施例3 超分子传感器BBI-WP5对Pb2+的检测
在超分子传感器BBI-WP5的水溶液(1×10-5mol/L)中,分别加入5倍当量的Ag+,Al3+, Ba2+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+,Fe3+,Hg2+,Mg2+,Ni2+,Pb2+,Zn2+的水溶液(0.1mol/L),若超分子传感器BBI-WP5的荧光打开,说明加入的是Pb2+,若超分子传感器BBI-WP5的荧光没有明显变化,说明加入的是其他金属离子。
Claims (7)
2.如权利要求1所述基于两亲性双苯并咪唑衍生物的超分子传感器在荧光识别Pb2+中的应用。
3.如权利要求2所述基于两亲性双苯并咪唑衍生物的超分子传感器在荧光识别Pb2+中的应用,其特征在于:在超分子传感器BBI-WP5中,分别加入Ag+, Al3+, Ba2+, Ca2+, Cd2+,Co2+, Cr3+, Cu2+,Fe3+,Hg2+,Mg2+,Ni2+,Pb2+,Zn2+的水溶液,只有Pb2+的加入能使超分子传感器BBI-WP5的荧光打开。
4.如权利要求1所述基于两亲性双苯并咪唑衍生物的超分子传感器,其特征在于:所述两亲性双苯并咪唑衍生物的合成方法,包括以下步骤:
(1)2,2’-双苯并咪唑的合成:将二水合草酸和邻苯二胺充分研磨混合均匀,加入多聚磷酸和乙二醇搅拌混合,在N2保护下,逐渐升温至沸腾,回流1~1.5 h,停止加热,待反应物冷却至60~80℃,倾入蒸馏水中,充分搅拌,静置,抽滤,滤饼转入20%的乙醇溶液中,搅拌分散后再抽滤,即得粗产物,粗产物转入醋酸中,加热至沸腾,使之全部溶解完全后冷却至室温,得金黄色蓬松的针状晶体,过滤,真空干燥,得2,2’-双苯并咪唑;
(2)1,1’-二溴己基-2,2’-双联苯并咪唑的合成:以DMF为溶剂,KOH粉末为催化剂,将2,2’-联苯并咪唑与1,6-二溴己烷在0~5℃下搅拌反应4~6h,用H2O和二氯甲烷进行萃取,下层滤液用无水硫酸钠干燥并蒸发,得到粗产物,然后通过柱色谱分离获得黄色固体粉末1,1’-二溴己基-2,2’-双苯并咪唑;
(3)两亲性双苯并咪唑衍生物的合成:用乙腈做溶剂,将1,1’-二溴己基-2,2’-双苯并咪唑与1-甲基咪唑在55~60℃下搅拌反应45~50小时,反应结束后进行蒸发浓缩,得到黄色固体即为目标产物两亲性双苯并咪唑衍生物BBI。
5.如权利要求4所述基于两亲性双苯并咪唑衍生物的超分子传感器,其特征在于:步骤(1)中,二水合草酸和邻苯二胺的摩尔比为1:2~1:2.5;二水合草酸与多聚磷酸的摩尔比为1:2~1:2.5。
6.如权利要求4所述基于两亲性双苯并咪唑衍生物的超分子传感器,其特征在于:步骤(2)中,2,2’-联苯并咪唑与1,6-二溴己烷的摩尔比为1:10~1:10.5;2,2’-联苯并咪唑与KOH粉末的摩尔比为1:4~1:4.5。
7.如权利要求4所述基于两亲性双苯并咪唑衍生物的超分子传感器,其特征在于:步骤(3)中,1,1’-二溴己基-2,2’-联苯并咪唑与1-甲基咪唑的摩尔比为1:5~1:5.5。
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