CN113651741B - 硫脲类希夫碱及其制备方法和作为Zn2+、Al3+荧光探针的应用 - Google Patents

硫脲类希夫碱及其制备方法和作为Zn2+、Al3+荧光探针的应用 Download PDF

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CN113651741B
CN113651741B CN202110760991.3A CN202110760991A CN113651741B CN 113651741 B CN113651741 B CN 113651741B CN 202110760991 A CN202110760991 A CN 202110760991A CN 113651741 B CN113651741 B CN 113651741B
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程景惠
曾露露
关会娟
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Abstract

本发明公开了一种硫脲类希夫碱及其制备方法和作为Zn2+、Al3+荧光探针的应用，硫脲类希夫碱包括硫脲类希夫碱L4(硫代氨基脲，4‑(二乙基氨基)水杨醛)、L5(硫代氨基脲、2‑羟基‑4‑甲氧基苯甲醛合成的希夫碱)、L11(硫代卡巴肼和2‑羟基‑4‑甲氧基苯甲醛)，L4、L5和L11在加入Zn2+后出现荧光增强，希夫碱配体对Zn2+具有很好的选择性，其他金属离子对Zn2+不存在干扰；此外L11配体在加入Al3+后也出现荧光增强，L11实现了对Zn2+和Al3+的双检测。硫脲类希夫碱作为Zn2+、Al3+荧光探针在环境监测和生物检测等领域具有重要的实际应用。

Description

硫脲类希夫碱及其制备方法和作为Zn2+、Al3+荧光探针的应用
技术领域
本发明涉及的是一种硫脲类希夫碱及其制备方法和作为Zn2+、Al3+荧光探针的应用。
背景技术
硫脲类希夫碱配体的结构特点决定其具有良好的光学性质，在一定条件下可以与多种金属离子进行螯合配位，这些配体和配合物在立体化学、结构学、立体异构、磁学、光谱学、配位化学、催化、分析化学、摄影、电光显示、农业以及光致变色等领域都有着重要的作用，一些硫脲类希夫碱配体已经被成功地应用到金属离子的荧光检测领域。荧光探针在生物领域中的应用引起了人们极大的兴趣。
大多数的传统有机发光材料都表现出自聚荧光淬灭现象，然而在实际生产和应用中往往需要有机发光材料在聚集态时具有优异的发光性能，这就严重制约了该领域的发展与应用前景。直到2001年唐本忠院士团队首次发现了与自聚荧光淬灭效应截然相反的现象，即有机发光材料在稀溶液状态下荧光很弱甚至没有荧光，但在聚集状态时荧光反而大幅度增强，该现象被称为“自聚诱导荧光”。
发明内容
本发明所要解决的技术问题是针对现有技术的不足提供一种硫脲类希夫碱及其制备方法和作为Zn2+、Al3+荧光探针的应用。通过引入含不同取代基的水杨醛衍生物与硫脲类化合物通过加成缩合反应合成一系列高灵敏度、高选择性的硫脲类希夫碱，及其作为Zn2 +、Al3+荧光探针在环境监测和生物检测等领域具有重要的实际应用和在聚集诱导荧光条件下对Al3+的比率式检测。
为实现上述目的，本发明采用的技术方案如下：
一种硫脲类希夫碱L4(硫代氨基脲，4-(二乙基氨基)水杨醛)；
L4的结构式为：
Figure BDA0003149724120000021
一种硫脲类希夫碱L5(硫代氨基脲、2-羟基-4-甲氧基苯甲醛合成的希夫碱)；
L5的结构式为：
Figure BDA0003149724120000022
一种硫脲类希夫碱L11(硫代卡巴肼和2-羟基-4-甲氧基苯甲醛)；
L11的结构式为：
Figure BDA0003149724120000023
所述L4的制备方法如下：
在100mL三口烧瓶中加入4mmol的4-(二乙基氨基)水杨醛，然后加入10-20mL 的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代氨基脲放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加0.5mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过过滤，得到棕黄色固体。
所述L5的制备方法如下：
在100mL三口烧瓶中加入4mmol的2-羟基-4-甲氧基苯甲醛，然后加入10-20mL 的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代氨基脲放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加0.5mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过过滤，得到黄色晶体。
所述L11的制备方法如下：
在100mL三口烧瓶中加入4mmol的2-羟基-4-甲氧基苯甲醛，然后加入10-20mL 的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代卡巴肼放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加1mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过过滤，得到浅绿色固体。
所述的硫脲类希夫碱配体L4在Zn2+探针中的应用，L4能实现对Zn2+的专一选择性识别。
所述的硫脲类希夫碱配体L5在Zn2+探针中的应用，L5能实现对Zn2+的专一选择性识别。
权利要求3所述的硫脲类希夫碱配体(L11)在Zn2+和Al3+探针中的应用，L11能够高选择性地识别Zn2+和Al3+。
所述的硫脲类希夫碱配体L11在聚集诱导荧光条件下对Al3+的比率式检测应用，L11 配体在聚集诱导荧光条件下实现比率式探针对金属离子的检测，实现高选择性和高灵敏性地识别金属离子。
其中L4、L5和L11在加入Zn2+后出现荧光增强，希夫碱配体对Zn2+具有很好的选择性，其他金属离子对Zn2+不存在干扰；此外L11配体在加入Al3+后也出现荧光增强， L11实现了对Zn2+和Al3+的双检测。硫脲类希夫碱作为Zn2+、Al3+荧光探针在环境监测和生物检测等领域具有重要的实际应用。
本发明还实现了在聚集诱导荧光条件下对金属离子的比率式检测，是双重信号单元的比率式探针，具有高选择性和高灵敏性。
附图说明
图1为L4的结构式；
图2为L5的结构式；
图3为L11的结构式；
图4为配体L4在乙腈(1.0×10-4mol·dm-3)体系中，在加入不同金属离子时的荧光发射光谱(激发波长380nm)；
图5为配体L5在乙腈(1.0×10-4mol·dm-3)体系中，在加入不同金属离子时的荧光发射光谱(激发波长380nm)；
图6为配体L11在乙腈(1.0×10-4mol·dm-3)体系中，在加入不同金属离子时的荧光发射光谱(激发波长350nm)；
图7为L11在不同f(水的体积分数)值的MeCN-H2O混合溶剂中的荧光发射光谱 (激发波长：400nm)；
图8为配体L11在MeCN-H2O混合溶剂中，在加入不同金属离子时的荧光发射光谱(激发波长390nm)；
具体实施方式
以下结合具体实施例，对本发明进行详细说明。
实施例1：硫脲类希夫碱配体的制备方法
L4的制备方法如下：
在100mL三口烧瓶中加入4mmol的4-(二乙基氨基)水杨醛，然后加入10-20mL 的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代氨基脲放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加0.5mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过抽滤，得到棕黄色固体。
上述的所有操作都是在避光环境下完成的，产率为76％。1H NMR(400MHz, DMSO-d6)δppm 1.12-1.16(12H,m),3.45-3.50(8H,m),6.56-6.59(2H,dd,J＝2Hz,6.4Hz), 6.77-6.79(2H,d,J＝8.4Hz),7.57-7.59(2H,d,J＝6.4Hz),8.18(1H,br),11.67(1H,br), 11.94(1H,br)
L5的制备方法如下：
在100mL三口烧瓶中加入4mmol的2-羟基-4-甲氧基苯甲醛，然后加入10-20mL 的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代氨基脲放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加0.5mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过抽滤，得到黄色晶体。产率为78％。1H NMR(400MHz,DMSO-d6)δppm 3.75(6H,m),6.55-6.58(2H,dd,J＝2Hz,6.3Hz), 6.76-6.78(2H,d,J＝8.3Hz),7.56-7.58(2H,d,J＝6.3Hz),8.13(1H,br),11.64(1H,br), 11.91(1H,br)
L11的制备方法如下：
在100mL三口烧瓶中加入4mmol的2-羟基-4-甲氧基苯甲醛，然后加入10-20mL 的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代卡巴肼放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加1mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过抽滤，得到浅绿色固体。
产率为89％1HNMR(400MHz,[D6]DMSO):δ＝7.23–7.25(d,2H),7.39–7.43(m,2H),7.59–7.63(m,2H),7.88–7.95(m,4H),8.24–8.52(br,2H),9.16–9.64(br,2H),10.61(br,1H),12.07(s,2H),12.88(br,1H)ppm.13C NMR(400MHz,[D6]DMSO):δ＝109.3,118.7, 121.0,123.5,127.8,127.9,128.7,131.7,132.6,145.8,157.1,174.0ppm.MS(EI):414.48.C23H18N4O2S(414.48):calcd.C 66.65,H 4.38,N13.52,S 7.74；found C 66.7,H 4.39,N13.51,S 7.72.
实施例2：硫脲类希夫碱配体(L4、L5)在Zn2+探针中的应用
通过L4和L5对14种金属离子进行识别，分别测定每次加入不同金属离子的荧光发射强度，可以得到其荧光发射光谱，由图4、图5所示，根据其荧光发射光谱图可以看出Zn2+的加入使L4、L5配体的荧光发射强度都显著增强，而加入Ag+,Al3+,Ce3+,Co2+, Cr2+,Cu2+,Mg2+,Mn2+,Na+,Ni2+,Cd2+,Pb2+和Sr2+后其荧光强度与希夫碱配体本身的荧光强度几乎相同，其荧光发射强度的增加与加入Zn2+离子相比可忽略不计，这说明L4 和L5实现了对Zn2+的专一选择性识别。
实施例3：硫脲类希夫碱配体(L11)在Zn2+和Al3+探针中的应用
通过L11对14种金属离子进行识别，分别测定每次加入不同金属离子的荧光发射强度，可以得到其荧光发射光谱，由图6所示，根据其荧光发射光谱图可以看出Zn2+和Al3+的加入使L11配体的荧光强度显著增强，与L4和L5相比，L11配体除了可以识别Zn2+外，还可以识别Al3+，并且Al3+加入后L11的荧光发射强度比Zn2+加入后的荧光强度高；而Na+,Ag+,Cd2+,Ce3+,Co2+,Cr2+,Cu2+,Mg2+,Mn2+,Ni2+,Pb2+和Sr2+后其荧光强度与希夫碱配体本身的荧光强度几乎相同，其荧光发射强度的增幅与加入Zn2+和Al3+相比可忽略不计。这说明L11能够高选择性地识别Zn2+和Al3+。
实施例4：硫脲类希夫碱配体(L11)在聚集诱导荧光条件下对Al3+的比率式检测
L11配体表现出非常明显的AIE效应，即在固态或水溶液中有较强的荧光，而在纯的有机溶剂乙腈稀溶液中表现出非常微弱的荧光。由图7所示，根据荧光发射光谱所示，希夫碱在有机溶剂乙腈中(水含量为0％)发光很弱，具有较大的斯托克斯位移，这可能是由于N-N单键的自由旋转和分子内质子快速转移过程所导致的。然而当水加入之后，分子发生自聚作用，形成纳米颗粒悬浊液，同时伴随荧光增强现象，当水的体积分数达到98％时，荧光强度达到最大值，即可得到L11的MeCN-H2O混合溶剂最佳的水含量为98％，因此基于此条件进行后续的L11配体在聚集诱导荧光条件下实现比率式探针对金属离子的检测，实现高选择性和高灵敏性地识别金属离子。
由图7可得L11的MeCN-H2O混合溶剂最佳的水含量为98％，在此条件下，通过 L11对14种金属离子进行识别，记录每次加入不同金属离子所对应的荧光强度，可以得到其荧光发射光谱，如图8所示，根据其荧光发射光谱可以看出，在发射波长为430nm 左右，Al3+的加入使L11配体的荧光发射强度显著增强，表现为蓝光；加入Cr2+,Zn2+,Al3+, Ag+,Cd2+,Ce3+,Mg2+,Co2+,Cu2+,Sr2+,Na+,Ni2+和Pb2+使L11配体在发射波长500nm左右的荧光显著淬灭。可以得出L11在聚集诱导荧光条件下作为比率式荧光探针检测金属离子，可以高选择性和高灵敏性地识别Al3+。
应当理解的是，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，而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 (7)

1.一种硫脲类希夫碱L4，L4的结构式为：
Figure FDA0003930851430000011
2.一种硫脲类希夫碱L5，L5的结构式为：
Figure FDA0003930851430000012
3.权利要求1所述的硫脲类希夫碱L4在Zn2+探针中的应用，L4能实现对Zn2+的专一选择性识别。
4.权利要求2所述的硫脲类希夫碱L5在Zn2+探针中的应用，L5能实现对Zn2+的专一选择性识别。
5.一种硫脲类希夫碱配体L11在Zn2+和Al3+探针中的应用，L11能够高选择性地识别Zn2+和Al3+，L11的结构式为：
Figure FDA0003930851430000021
6.权利要求1所述的硫脲类希夫碱L4的制备方法，其特征在于，制备方法如下：
在100mL三口烧瓶中加入4mmol的4-(二乙基氨基)水杨醛，然后加入10-20mL的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代氨基脲放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加0.5mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过过滤，得到棕黄色固体。
7.权利要求2所述的硫脲类希夫碱L5的制备方法，其特征在于，制备方法如下：
在100mL三口烧瓶中加入4mmol的2-羟基-4-甲氧基苯甲醛，然后加入10-20mL的无水乙醇，在油浴锅中80℃加热至溶解完全，将2mmol硫代氨基脲放入小烧杯中加入50mL乙醇完全溶解后，逐滴滴加到三口烧瓶的反应混合液中，最后滴加0.5mL三乙胺做催化剂，在油浴锅中80℃冷凝回流5h，通过过滤，得到黄色晶体。
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