CN108250198B - 一种久洛尼定衍生物及其制备方法和应用 - Google Patents

一种久洛尼定衍生物及其制备方法和应用 Download PDF

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CN108250198B
CN108250198B CN201810230541.1A CN201810230541A CN108250198B CN 108250198 B CN108250198 B CN 108250198B CN 201810230541 A CN201810230541 A CN 201810230541A CN 108250198 B CN108250198 B CN 108250198B
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徐鉴
张长丽
刘光祥
赵海荣
刘少贤
石翛然
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Nanjing Xiaozhuang University
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Abstract

本发明公开了一种久洛尼定衍生物及其制备方法和应用，属于环境检测领域。该方法是在酸性条件下，将2,3‑二氨基萘、有机溶剂和除水剂混合后加热回流，之后在保护气体的作用下，缓慢加入含8‑羟基久洛尼定‑9‑甲醛的有机溶剂溶液，之后继续反应18~30h，反应结束后过滤、蒸干、重结晶得到久洛尼定衍生物。本发明所述的久洛尼定衍生物制备方法简单，容易工业化应用。且所述的衍生物对Cu2+灵敏度高，检测限低。

Description

一种久洛尼定衍生物及其制备方法和应用
技术领域
本发明属于环境检测领域，具体涉及一种久洛尼定衍生物及其制备方法和应用。
背景技术
铜是人体内继铁、锌之后第三丰富的过渡金属元素。Cu2+在人体内的适量存在有益于维持机体的正常工作。Cu2+能参与体内酶反应、酶转录及一些氧化还原过程，同时还与人处于压力与恐慌下的生理反应密切相关。若体内Cu2+的代谢不正常，则可能诱发一系列疾病，如Menkes综合症、Wilsom综合症、家族性肌萎缩症、阿尔茨海默氏症等；当人体内Cu2+含量过高，会产生巨大的毒害作用。因此，设计并开发一种具有高灵敏度，高选择性检测Cu2+的手段具有重要意义。
发明内容
本发明是针对上述存在的技术问题提供一种久洛尼定衍生物及其制备方法和应用。
本发明的目的可以通过以下技术方案实现：
一种久洛尼定衍生物，该衍生物的结构式如下所示：
一种上述的久洛尼定衍生物的制备方法，该方法的反应路线如下：
在一些具体的技术方案中：该方法是在酸性条件下，将2,3-二氨基萘、有机溶剂和除水剂混合后加热回流，之后在保护气体的作用下，缓慢加入含8-羟基久洛尼定-9-甲醛的有机溶剂溶液，之后继续反应18～30h，反应结束后过滤、蒸干、重结晶得到久洛尼定衍生物。
在一些优选的技术方案中：所述的有机溶剂为含有1～5个碳原子的醇或烷基取代苯。
在一些更为优选的技术方案中：所述的有机溶剂为含有1～3个碳原子的醇或甲苯。
在一些最优选的技术方案中：所述的有机溶剂甲醇、乙醇或者甲苯。
在一些技术方案中：酸性试剂与8-羟基久洛尼定-9-甲醛的体积摩尔比为1-15mL：1mol，且所述的酸性试剂为冰醋酸、浓盐酸或浓硫酸。
本发明技术方案所述的久洛尼定衍生物在检测Cu2+中的应用。
本发明技术方案所述的久洛尼定衍生物作为荧光化学传感器在检测Cu2+中的应用。
本发明的有益效果：
本发明所述的久洛尼定衍生物制备方法简单，容易工业化应用。且所述的衍生物对Cu2+灵敏度高，检测限低。
附图说明
图1为探针分子AMHQ对Cu2+的选择性吸收光谱识别。
图2为Cu2+对探针分子AMHQ的吸收光谱滴定图。
图3为探针分子AMHQ对Cu2+的选择性荧光光谱识别。
图4为Cu2+对探针分子AMHQ的荧光光谱滴定图。
图5为Cu2+与探针分子AMHQ反应时间对溶液荧光强度的影响图。
图6为当溶液中有其它共存金属离子时对探针AMHQ选择性识别Cu2+的影响图。
图7为不同pH值对探针AMHQ选择性识别Cu2+的影响图。
具体实施方式
下面结合实施例对本发明做进一步说明，但本发明的保护范围不限于此：
实施例1
在500mL的三颈烧瓶中依次加入150mL无水乙醇、2,3-二氨基萘(1.74g，11mmol)、0.1mL冰醋酸和活化分子筛(1.0g)，加热回流。在通入N2的条件下，用恒压漏斗缓慢滴加溶有8-羟基久洛尼定-9-甲醛(2.17g，10mmol)的80mL无水乙醇溶液，滴加完毕后继续反应24h，待反应结束后趁热过滤除去活化分子筛，将滤液旋转蒸干得粗产物，将此粗产物用无水乙醇重结晶，得黄色晶体产物Ⅲ(AMHQ)3.35g，产率93.8％，纯度99.31％。元素分析：(％)Caled for C23H23N3O:C 77.28；H 6.49；N 11.76,found:C 77.52；H 6.32；N11.68。
1H NMR(500MHz,CDCl3):δ＝11.84(s,1H),8.34(s,1H),7.88-7.83(m,2H),7.68-7.62(m,2H),7.36(t,1H),7.18(t,1H),6.82(s,1H),4.82(d,2H),3.24(m,4H),2.54(m,4H),1.52(m,4H)ppm.13C NMR(100MHz,CDCl3):δ＝164.28,159.07,149.16,142.43,141.17,134.28,132.26,129.30,128.27,125.89,118.11,115.26,113.16,107.87,105.34,101.20,98.94,50.26,49.53,27.25,21.69,20.63,20.34.
实施例2
在500mL的三颈烧瓶中依次加入150mL无水甲醇、2,3-二氨基萘(1.90g，12mmol)、0.08mL浓盐酸和无水硫酸钠(1.0g)，加热回流。在通入N2的条件下，用恒压漏斗缓慢滴加溶有8-羟基久洛尼定-9-甲醛(2.17g，10mmol)的80mL无水甲醇溶液，滴加完毕后继续反应24h，待反应结束后趁热过滤除去硫酸钠，将滤液旋转蒸干得粗产物，将此粗产物用无水乙醇重结晶，得黄色晶体产物Ⅲ(AMHQ)3.27g，产率91.6％，纯度99.23％。
实施例3
在500mL的三颈烧瓶中依次加入150mL甲苯、2,3-二氨基萘(2.21g，14mmol)、0.05mL浓硫酸和无水硫酸镁(1.0g)，加热回流。在通入N2的条件下，用恒压漏斗缓慢滴加溶有8-羟基久洛尼定-9-甲醛(2.17g，10mmol)的80mL甲苯溶液，滴加完毕后继续反应24h，待反应结束后趁热过滤除去硫酸镁，将滤液旋转蒸干得粗产物，将此粗产物用无水乙醇重结晶，得黄色晶体产物Ⅲ(AMHQ)3.21g，产率89.9％，纯度99.12％。
性质部分
1、吸收光谱实验
久洛尼定衍生物AMHQ对Cu2+的吸收光谱识别
图1是探针分子AMHQ对Cu2+的选择性吸收光谱识别。在10mL浓度为0.1mmol/L探针分子AMHQ溶液中分别加入10μL浓度为0.2mol/L(2倍摩尔量)的金属离子溶液(Cu2+、Zn2+、Al3 +、Co2+、Na+、Ca2+、Cd2+、Ni2+、Hg2+、Mg2+、K+、Pb2+)。实验中所使用的溶液体系均为乙腈/水(1:3，v:v)的混合溶液，吸收光谱在岛津UV-2450型紫外分光光度计上测定。
由图1可以看出探针分子在乙腈/水(1:3，v:v)的混合溶液中自身的吸收在460nm左右，当我们向探针分子溶液中加入过量的金属离子后，我们发现只有在加入Cu 2+后，溶液的吸收红移至535nm左右，溶液的颜色也由黄色变为橘色，而当在探针分子溶液中加入其它金属离子时，则没有这一现象的发生，这说明该探针分子的吸收光谱对Cu2+有着独特的响应，可以对Cu2+进行裸眼识别。
图2为Cu2+对探针分子AMHQ的吸收光谱滴定图。在10mL浓度为0.1mmol/L探针
AMHQ溶液中依次加入0.1、0.2、0.3、0.4、0.5、0.6、0.7、0.8、0.9、1.0、1.2、1.5倍摩尔量的Cu2+。实验中所使用的溶液体系均为乙腈/水(1:3，v:v)的混合溶液，吸收光谱在岛津UV-2450型紫外分光光度计上测定。由图2可以看出，随着Cu2+的加入，溶液的吸收波长逐渐由460nm红移至535nm，当Cu2+加入量达到探针分子1倍摩尔量后，溶液的吸收波长不再移动，且峰的强度基本不变。这说明探针分子AMHQ与Cu2+是1:1配位的。
2、荧光光谱实验
久洛尼定衍生物AMHQ对Cu2+的荧光识别
图3是探针分子AMHQ对Cu2+的选择性荧光光谱识别。将探针分子AMHQ溶于乙腈/水(1:3，v:v)的混合溶液中，配制成浓度为10μmol/L的溶液，在此溶液中分别加入2倍摩尔量的金属离子(Cu2+、Zn2+、Al3+、Co2+、Na+、Ca2+、Cd2+、Ni2+、Hg2+、Mg2+、K+、Pb2+)。激发波长为535nm，测定溶液的荧光光谱。从图3中可以看出，探针分子溶液无荧光发射峰，在加入Cu2+后，溶液在563nm处出现一个很强的荧光发射峰，而加入其它金属离子则没有这一现象，这说明该探针分子对Cu2+表现出非常强的荧光选择识别性。实验中所使用的溶液体系均为乙腈/水(1:3，v:v)的混合溶液，荧光光谱在AMINCO Bowman Series 2荧光光谱仪上测得。
图4为Cu2+对探针分子AMHQ的荧光光谱滴定图。在10μmol/L的探针分子AMHQ的乙腈/水(1:3，v:v)的混合溶液中，分别加入0.1、0.2、0.3、0.4、0.5、0.6、0.7、0.8、0.9、1.0、1.2、1.5倍摩尔量的Cu2+。在535nm处激发，测量溶液的发射光谱，如图所示随着Cu2+的浓度增加，在563nm处出现一个新的荧光发射峰，并且在Cu2+加入量达到1倍摩尔量后563nm处的发射峰强度基本不再增加。
图5为Cu2+与探针分子AMHQ反应时间对溶液荧光强度的影响图。在10μmol/L的探针分子AMHQ的乙腈/水(1:3，v:v)的混合溶液中，加入1倍摩尔量的Cu2+。在激发波长535nm，发射波长563nm条件下，分别在0、1、2、3、4、5、6、7分钟时记录溶液的荧光强度。如图所示，在探针分子AMHQ溶液中加入Cu2+4分钟后，荧光强度达到最大值，且随着时间延长基本保持不变。这说明该探针分子可以和Cu2+快速反应，且生成的配合物稳定。
图6为当溶液中有其它共存金属离子时对探针AMHQ选择性识别Cu2+的影响图。在10μmol/L的探针分子AMHQ的乙腈/水(1:3，v:v)的混合溶液中，分别加入溶有10倍摩尔量的金属离子(Zn2+、Al3+、Co2+、Na+、Ca2+、Cd2+、Ni2+、Hg2+、Mg2+、K+、Pb2+)，在激发波长535nm，发射波长563nm条件，测量溶液的荧光强度，然后再在上述溶液中加入10倍摩尔量的Cu2+，在激发波长535nm，发射波长563nm条件下，测量溶液的荧光强度，从图6中可以看出，当溶液中大量存在其他金属离子时，探针分子AMHQ对Cu2+的选择性识别并不受影响。
图7为不同pH值对探针AMHQ选择性识别Cu2+的影响图。分别用不同浓度的盐酸或氢氧化钠溶液以调节10μmol/L的探针分子AMHQ的乙腈/水(1:3，v:v)的混合溶液的pH值，在激发波长535nm，发射波长563nm条件下，测量探针溶液的荧光强度；然后再在以上溶液中分别加入1倍摩尔量的Cu2+，在激发波长535nm，发射波长563nm条件下，测量溶液的荧光强度。从图7中可以看出，在pH＝5-9的范围内探针分子对Cu2+都具有很好荧光响应，并且比较稳定，这说明该探针可以在更宽泛的环境中检测Cu2+。

Claims (9)

1.一种久洛尼定衍生物，其特征在于：该衍生物的结构式如下所示：
2.一种权利要求1所述的久洛尼定衍生物的制备方法，其特征在于：
3.根据权利要求2所述的久洛尼定衍生物的制备方法，其特征在于：该方法是在酸性条件下，将2,3-二氨基萘、有机溶剂和除水剂混合后加热回流，之后在保护气体的作用下，缓慢加入含8-羟基久洛尼定-9-甲醛的有机溶剂溶液，之后继续反应18～30h，反应结束后过滤、蒸干、重结晶，即可得到久洛尼定衍生物。
4.根据权利要求3所述的久洛尼定衍生物的制备方法，其特征在于：所述的有机溶剂为含有1～5个碳原子的醇或烷基取代苯。
5.根据权利要求4所述的久洛尼定衍生物的制备方法，其特征在于：所述的有机溶剂为含有1～3个碳原子的醇或甲苯。
6.根据权利要求5所述的久洛尼定衍生物的制备方法，其特征在于：所述的有机溶剂为甲醇、乙醇或者甲苯。
7.根据权利要求3所述的久洛尼定衍生物的制备方法，其特征在于：酸性试剂与8-羟基久洛尼定-9-甲醛的体积摩尔比为1-15mL：1mol，且所述的酸性试剂为冰醋酸、浓盐酸或浓硫酸。
8.权利要求1所述的久洛尼定衍生物在检测Cu2+中的应用。
9.权利要求1所述的久洛尼定衍生物作为荧光化学传感器在检测Cu2+中的应用。
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