CN107235849B - 一种查尔酮基荧光传感器及其制备方法与应用 - Google Patents
一种查尔酮基荧光传感器及其制备方法与应用 Download PDFInfo
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Abstract
本发明公开了一种查尔酮基荧光传感器及其制备方法与应用,其具有如下通式所示的结构:其中,R1、R2均为芳香族取代基。本发明的查尔酮基荧光传感器能够利用紫外‑可见吸收法和荧光法双通道,对肼分子进行快速、高选择性和高灵敏度的检测;另外,本发明制备方法简单,原料便宜易得,使用方便,具有较好的工业化应用前景。
Description
技术领域
本发明涉及荧光传感领域,尤其涉及一种查尔酮基荧光传感器及其制备方法与应用。
背景技术
肼分子早在20世纪40年代就被用作一种火箭推进燃料,近年来更是广泛的应用于化工产业,包括工业塑料发泡剂、合成药物以及合成农药。在2007年,世界范围内肼的工业产能已经达到20万吨。随着药物合成化学和航空航天工业的快速发展,肼分子在制造、运输和后处理过程中存在泄漏的风险。然而,肼分子对脊椎动物都具有很大的生物毒性。将过量肼分子掺水喂食小鼠后,小鼠的肺肿瘤和肝肿瘤的发生率大大提高;同时,肼分子也会直接刺激人类的眼睛和皮肤,过量误服会对肝脏、肾脏和中枢神经系统造成不可逆的损害。因此,世界卫生组织(WHO)将肼分子列为可能致癌的环境污染物之一,职业安全与卫生管理局(OSHA)也建议食物或水中含有的肼分子的浓度应低于1ppm。因此,发展一种简易、快速、灵敏的肼分子检测方法极为重要。
目前,用于水样和环境中肼含量的检测方法主要有气相色谱法、化学滴定法和电化学方法。但是现有这些检测方法存在检测步骤复杂,检测速度慢及对肼分子识别性较低的问题。
因此,现有技术还有待于改进和发展。
发明内容
鉴于上述现有技术的不足,本发明的目的在于提供一种查尔酮基荧光传感器及其制备方法与应用,旨在解决现有肼分子检测方法过于复杂、检测速度慢及对肼分子识别性较低的问题。
本发明的技术方案如下:
一种查尔酮基荧光传感器,其中,具有如下通式所示的结构:
其中,R1、R2均为芳香族取代基。
所述的查尔酮基荧光传感器,其中,所述R1为如下结构中的一种:
所述的查尔酮基荧光传感器,其中,所述R2为如下结构中的一种:
一种如上任一所述的查尔酮基荧光传感器的制备方法,其中,包括步骤:将含R1取代基的乙酮与含R2取代基的对氨基苯甲醛加入至有机溶剂中,然后加入碱溶液,在0-70摄氏度下搅拌1-24小时后,加入至冰水中,然后用酸中和,再经提纯处理得到查尔酮基荧光传感器。
所述的查尔酮基荧光传感器的制备方法,其中,所述含R1取代基的乙酮与含R2取代基的对氨基苯甲醛的摩尔比为1:1-3。
所述的查尔酮基荧光传感器的制备方法,其中,所述有机溶剂为乙醇与四氢呋喃的混合溶液,所述乙醇与四氢呋喃的体积比为5-30:1。
所述的查尔酮基荧光传感器的制备方法,其中,所述碱溶液为氢氧化钾水溶液,所述氢氧化钾水溶液的浓度为5-25%wt。
所述的查尔酮基荧光传感器的制备方法,其中,所述酸为盐酸,所述盐酸的浓度为1M。
所述的查尔酮基荧光传感器的制备方法,其中,所述提纯处理的过程具体为:加入二氯甲烷萃取,萃取液分别用饱和食盐水以及去离子水洗三次,经无水硫酸钠干燥,然后过滤、减压蒸馏获得粗产物,粗产物再经重结晶或柱色谱分离法获得查尔酮基荧光传感器。
一种如上任一所述的查尔酮基荧光传感器的应用,其中,用于检测肼分子。有益效果:本发明上述查尔酮基荧光传感器能够利用紫外-可见吸收法和荧光法双通道,对肼分子进行快速、高选择性和高灵敏度的检测。
附图说明
图1为本发明实施例1中查尔酮基荧光传感器TAPHP的吸收光谱对肼分子的响应图;
图2为本发明实施例1中查尔酮基荧光传感器TAPHP在350纳米光激发下的荧光光谱对肼分子的响应图;
图3为本发明实施例1中查尔酮基荧光传感器TAPHP在450纳米光激发下的荧光光谱对肼分子的响应图。
图4为本发明实施例1中查尔酮基荧光传感器TAPHP对肼分子选择性识别的示意图。
具体实施方式
本发明提供了一种查尔酮基荧光传感器及其制备方法与应用,为使本发明的目的、技术方案及效果更加清楚、明确,以下对本发明进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
本发明提供一种查尔酮基荧光传感器较佳实施例,具有如下通式所示的结构:
式I中,R1取代基属于芳香族取代基,具体地,所述R1可以为如下结构中的一种:
式I中,R2取代基属于芳香族取代基,具体地,所述R2可以为如下结构中的一种:
本发明上述结构的查尔酮基荧光传感器,能够利用紫外-可见吸收法和荧光法双通道,对肼分子进行快速、高选择性和高灵敏度的比率法检测,大大提高了检测准确度。
本发明还提供一种如上所述查尔酮基荧光传感器的制备方法,包括步骤:将含R1取代基的乙酮与含R2取代基的对氨基苯甲醛,优选的按照摩尔比1:1-3(如分别取10毫摩尔)加入至有机溶剂中,优选30-300毫升的乙醇与四氢呋喃的混合溶液(体积比为5-30:1,如5:1、9:1或30:1)作为有机溶剂,然后逐滴加入2-20毫升碱溶液(如氢氧化钾水溶液,优选质量浓度为5-25%wt),接着在0-70摄氏度下搅拌1-24小时后,倒入至500毫升-2升冰水中,用酸,如稀盐酸(1M)中和至pH=7,加入二氯甲烷萃取。萃取液分别用饱和食盐水以及去离子水洗三次,经无水硫酸钠干燥,再经过滤、减压蒸馏获得粗产物,最后粗产物经重结晶或柱色谱分离法获得纯的查尔酮基荧光传感器。反应方程式如下式II所示:
本发明以芳香基乙酮和二芳香氨基苯甲醛为原料,通过醛酮缩合反应,制备得到查尔酮基荧光传感器。本发明该制备方法简单,原料便宜易得。
本发明还提供了一种如上所述查尔酮基荧光传感器的应用,其中,用于检测肼分子。本发明查尔酮基荧光传感器能够利用紫外-可见吸收法和荧光法双通道,对肼分子实现快速、高选择性、高灵敏度的检测,具有较好的工业化应用前景。
下面通过实施例对本发明进行详细说明。
实施例1
查尔酮基荧光传感器3-(4-(二对甲苯胺基)苯基)-1-(2-羟基苯基)丙-2-烯-1-酮(TAPHP)的制备
将10毫摩尔临羟基苯乙酮与10毫摩尔4-(二对甲苯胺基)苯甲醛加入至反应器中,加入50毫升的乙醇与四氢呋喃的混合溶液(体积比为9:1)做为溶剂,逐滴加入10毫升氢氧化钾水溶液(15%wt),在40摄氏度搅拌24小时后,倒入至500毫升冰水中,用稀盐酸(1M)中和至pH=7,加入100毫升二氯甲烷萃取3次。萃取液分别用饱和食盐水以及去离子水洗三次,经无水硫酸钠干燥,过滤后减压蒸馏获得粗产物。粗产物在乙醇中重结晶,获得纯的查尔酮基荧光传感器TAPHP,其结构式如下:
实施例2
查尔酮基荧光传感器3-(4-(二对甲苯胺基)苯基)-1-(2-羟基-5-甲氧基苯基)丙-2-烯-1-酮的制备
将10毫摩尔2-羟基-4-甲氧基苯乙酮与10毫摩尔4-(二对甲苯胺基)苯甲醛加入至反应器中,加入100毫升的乙醇与四氢呋喃的混合溶液(体积比为30:1)做为溶剂,逐滴加入10毫升氢氧化钾水溶液(20%wt),在60摄氏度搅拌4小时后,倒入至1升冰水中,用稀盐酸(1M)中和至pH=7,加入200毫升二氯甲烷萃取。萃取液分别用饱和食盐水以及去离子水洗三次,经无水硫酸钠干燥,过滤后减压蒸馏获得粗产物。粗产物由柱色谱分离法(洗脱液为二氯甲烷)获得纯的查尔酮基荧光传感器,其结构式如下:
实施例3
查尔酮基荧光传感器3-(4-(双(对甲氧基苯基)胺基)苯基)-1-(5-氟-5-羟基苯基)丙-2-烯-1-酮的制备
将10毫摩尔5-氟-2-羟基苯乙酮与10毫摩尔4-(双(对甲氧基苯基)胺基)苯甲醛加入至反应器中,加入50毫升的乙醇与四氢呋喃的混合溶液(体积比为5:1)做为溶剂,逐滴加入20毫升氢氧化钾水溶液(10%wt),在25摄氏度搅拌24小时后,倒入至1升冰水中,用稀盐酸(1M)中和至pH=7,加入100毫升二氯甲烷萃取。萃取液分别用饱和食盐水以及去离子水洗三次,经无水硫酸钠干燥,过滤后减压蒸馏获得粗产物。粗产物由柱色谱分离法(洗脱液为乙酸乙酯/正己烷)获得纯的查尔酮基荧光传感器,其结构式如下:
实施例4
查尔酮基荧光传感器TAPHP对肼分子的检测
如图1所示,向10微摩尔每升的查尔酮基荧光传感器TAPHP中加入100微摩尔每升的肼分子后,TAPHP在450纳米处的吸收峰逐渐降低至几乎消失,肉眼观测,TAPHP由黄色液体逐渐变为无色液体。
如图2所示,在350纳米的激发光照射下,TAPHP能够发射出较弱的380纳米荧光,向10微摩尔每升的查尔酮基荧光传感器TAPHP中加入100微摩尔每升的肼分子后,在350纳米的激发光照射下,TAPHP的荧光发射峰逐渐增强并红移至410纳米。
如图3所示,在450纳米的激发光照射下,TAPHP能够发射出很强的610纳米红色荧光,向10微摩尔每升的查尔酮基荧光传感器TAPHP加入100微摩尔每升的肼分子后,在450纳米的激发光照射下,TAPHP的荧光发射峰逐渐降低并蓝移至520纳米的蓝绿色荧光。
在380纳米紫外灯照射下,浓度10微摩尔每升TAPHP能够发出橙黄色荧光,向TAPHP溶液中加入100微摩尔每升的肼分子后,TAPHP的荧光由橙黄色变为亮蓝色,而向TAPHP溶液中分别加入100微摩尔每升的羟胺、苯肼、氨水、哌嗪、三乙胺、十二胺以及三甲基十二烷基氯化铵后,TAPHP的荧光基本保持不变。只有苯肼使得TAPHP的荧光由橙黄色稍微变为黄色,证明TAPHP能够选择性检测肼分子。如图4所示,传感器TAPHP的初始蓝光红光强度比(I410/I610)约为2左右,在加入肼分子之后,传感器TAPHP的蓝光红光强度比(I410/I610)大幅增加至80以上,而加入其它的胺类化合物后,其蓝光红光强度比(I410/I610)并没有明显提高,证明了TAPHP能够选择性检测肼分子。
综上所述,本发明提供了一种查尔酮基荧光传感器及其制备方法与应用,本发明的查尔酮基荧光传感器能够利用紫外-可见吸收法和荧光法双通道,对肼分子进行快速、高选择性和高灵敏度的检测;另外,本发明制备方法简单,原料便宜易得,使用方便,具有较好的工业化应用前景。
应当理解的是,本发明的应用不限于上述的举例,对本领域普通技术人员来说,可以根据上述说明加以改进或变换,所有这些改进和变换都应属于本发明所附权利要求的保护范围。
Claims (1)
1.一种查尔酮基荧光传感器的应用,其特征在于,用于检测肼分子,所述查尔酮基荧光传感器具有如下通式所示的结构:
其中,R1、R2均为芳香族取代基;
所述R1为如下结构中的一种:
所述R2为如下结构中的一种:
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