基于催化反应的荧光探针及其在气体发生剂中铜含量的检测应用

doi:10.6023/cjoc202504007

有机化学 ›› 2025, Vol. 45 ›› Issue (11): 4195-4201.DOI: 10.6023/cjoc202504007 上一篇下一篇

研究论文

基于催化反应的荧光探针及其在气体发生剂中铜含量的检测应用

程晓红^a^,^*(), 张仁杰^b, 游军^b, 付文斌^b, 沈文洁^b, 罗运强^b, 王松^a

^a 湖北文理学院 “低维光电材料与器件”湖北省重点实验室 “低维光电材料与器件”湖北省重点实验室湖北襄阳 441053
^b 湖北航鹏化学动力科技有限责任公司湖北襄阳 441003

收稿日期:2025-04-07 修回日期:2025-05-09 发布日期:2025-06-19
基金资助:
湖北省教育厅科技研究(D20232601); 与湖北省自然科学基金创新发展联合基金(2025AFD025)

A Novel Catalytic Fluorescent Probe and Its Application in Copper Detection in Gas-Generating Agents

Xiaohong Cheng^a^,^*(), Renjie Zhang^b, Jun You^b, Wenbin Fu^b, Wenjie Shen^b, Yunqiang Luo^b, Song Wang^a

^a Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices, Hubei University of Arts and Science, Xiangyang, Hubei 441053
^b Hubei Hangpeng Chemical Power Technology Co., Ltd., Xiangyang, Hubei 441003

Received:2025-04-07 Revised:2025-05-09 Published:2025-06-19
Contact: *E-mail: chengxiaohong0807@126.com
Supported by:
Science and Technology Research Project of Department of Education of Hubei Province(D20232601); Joint Foundation for Innovation and Development of Hubei Natural Science Foundation(2025AFD025)

文章分享

1. 附件.pdf(2324KB)

摘要/Abstract

报道了基于香豆素衍生物的荧光增强型探针C2, 铜离子的加入会诱导C2中苯腙部分发生水解断裂, 生成相应的醛类化合物, 导致溶液荧光明显增强. 探针C2可实现对铜离子的高灵敏度检测, 检测限低至150 nmol/L. 得益于该独特的催化水解反应, 化合物C2对铜离子表现出超高的选择性, 即使在竞争离子共存的情况下, 对铜离子仍表现出特异性的识别与响应. 荧光强度的变化与铜离子浓度呈现出良好的线性关系, 可实现对铜离子的精确定量检测. 重要的是, 探针C2可成功地应用于气体发生剂的实际检测中.

关键词: 荧光探针, 铜离子, 催化水解, 高灵敏度, 气体发生剂检测

A new coumarin derivative C2 was constructed to act as a highly effective turn-on fluorescent probe for Cu^2＋ ions. The introduction of Cu^2＋ could lead to the hydrolytic cleavage of the phenylhydrazone moiety in C2 and the transformation into strongly fluorescent aldehyde C1. Probe C2 could recognize Cu^2＋ through a marked fluorescence enhancement with the detection limit as low as 150 nmol/L. By virtue of this unique catalytic hydrolysis reaction, compound C2 displayed highly selective response toward Cu^2＋ over other common ions even in the presence of excessive competitive ions. Furthermore, there was a good linear relationship between the intensity change and the concentration of Cu^2＋ ions, which was beneficial for the exactly quantitative detection. Especially, the efficient detection of Cu^2＋ with C2 for the practical application was successfully performed in gas-generating agents detection

Key words: fluorescent probe, copper ions, catalytic hydrolysis, high sensitivity, gas-generating agents detection

引用此文

程晓红, 张仁杰, 游军, 付文斌, 沈文洁, 罗运强, 王松. 基于催化反应的荧光探针及其在气体发生剂中铜含量的检测应用[J]. 有机化学, 2025, 45(11): 4195-4201.

Xiaohong Cheng, Renjie Zhang, Jun You, Wenbin Fu, Wenjie Shen, Yunqiang Luo, Song Wang. A Novel Catalytic Fluorescent Probe and Its Application in Copper Detection in Gas-Generating Agents[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4195-4201.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 6

Scheme 1. Structures of compounds C1 and C2 and the sensing process

Figure 1. Reaction-time profile of C2 (10 μmol/L) in the presence of different concentrations of Cu2＋ ions excited at 410 nm

Figure 2. Fluorescent emission spectra of C2 (10 μmol/L, in THF/HEPES, V∶V=1∶9, pH 7.1) in the presence of different concentrations of Cu2＋ excited at 410 nm Inset: fluorescent photograph of C2 and C2＋Cu2＋.

Figure 3. Plot of fluorescent intensity at 490 nm of C2 as a function of the concentration of Cu2＋ ions

Figure 4. Emission intensity changes of C2 to Cu2＋ (35 μmol/L) in the presence of other competitive species (100 μmol/L) The error bars represent the standard deviation of three measurements

Figure 5. 1H NMR spectra of compound C2 (a) and its hydrolysis reaction product with Cu2＋ (b) in CDCl3 (the signal of the solvent was marked with an asterisk)

参考文献 5

[5]	(k) Yang, Y.; Cao, B.; Zhang, Y.; Dong, Y. Chin. J. Org. Chem. 2017, 37, 3024 (in Chinese). doi: 10.6023/cjoc201702024
	(杨云裳, 曹碧霞, 张应鹏, 董玉莹, 有机化学, 2017, 37, 3024.) doi: 10.6023/cjoc201702024
	(l) Chen, H.; Yang, P.; Li, Y.; Zhang, L.; Ding, F.; He, X.; Shen, J. Spectrochim. Acta, Part A 2020, 224, 117384. doi: 10.1016/j.saa.2019.117384
[6]	Corey, E. J.; Knapp, S. Tetrahedron Lett. 1976, 17, 3667. doi: 10.1016/S0040-4039(00)93076-4
[7]	(a) Ahmed, N.; Zareen, W.; Zhang, D.; Yang, X.; Ye, Y. J. Fluoresc. 2020, 30, 1171. doi: 10.1007/s10895-020-02585-0
	(b) Cao, X.; Lin, W.; Yu, Q.; Wang, J. Org. Lett. 2011, 13, 6098. doi: 10.1021/ol202595t
	(c) Jung, H. S.; Kwon, P. S.; Lee, J. W.; Kim, J. II.; Hong, C. S.; Kim, J. W.; Yan, S.; Lee, J. Y.; Lee, J. H.; Joo, T.; Kim, J. S. J. Am. Chem. Soc. 2009, 131, 2008. doi: 10.1021/ja808611d
[1]	Ge, Y.; Xu, T.; Yang, J.; Cheng, Y. Explos. Mater. 2001, 43, 35.
[2]	Deng, K.; Tao, Z. J. Solid Rocket Technol. 1996, 19, 34 (in Chinese).
	(邓康清, 陶自成, 固体火箭技术, 1996, 19, 34.)
[3]	Zhang, S.; Han, L.; Wang, X. J. Luoyang Normal Univ. 2006, 5, 74 (in Chinese).
	(张苏杭, 韩琳, 王新德, 洛阳师范学院学报, 2006, 5, 74.)
[4]	Date, S.; Sugiyama, T.; Itadzu, N. Propellants, Explos., yrotech. 2011, 36, 51.
[5]	(a) Wu, M.; You, J.; Yu, Y.; Wu, W. Chin. J. Org. Chem. 2022, 42, 2559 (in Chinese). doi: 10.6023/cjoc202203009
	(吴绵园, 由君, 喻艳超, 武文菊, 有机化学, 2022, 42, 2559.) doi: 10.6023/cjoc202203009
	(b) Bhardwaj, K.; Anand, T.; Jangir, R.; Sahoo, S. K. J. Fluoresc. 2024, 34, 1065. doi: 10.1007/s10895-023-03347-4
	(c) He, J.; Xie, Z.; Xue, S.; Liu, Y.; Shi, W.; Chen, X. Chin. J. Org. Chem. 2021, 41, 2839 (in Chinese). doi: 10.6023/cjoc202102013
[7]	(d) Choi, M. G.; Hwang, J.; Moon, J. O.; Sung, J.; Chang, S.-K. Org. Lett. 2011, 13, 5260. doi: 10.1021/ol202136q
[8]	(a) Xiang, Y.; Tong, A.; Jin, P.; Ju, Y. Org. Lett. 2006, 8, 2863. pmid: 23223311
	(b) Zhao, N.; Wu, Y.; Luo, J.; Shi, L.; Chen, Z. Analyst 2013, 138, 894. doi: 10.1039/c2an36501d pmid: 23223311
	(c) Feng, L.; Li, H.; Lv, Y.; Guan, Y. Analyst 2012, 137, 5829. doi: 10.1039/c2an36215e pmid: 23223311
[9]	Wu, J.; Liu, W.; Ge, J.; Zhang, H.; Wang, P. Chem. Soc. Rev. 2011, 40, 3483. doi: 10.1039/c0cs00224k
[10]	Liu, L.; Dong, X.; Xiao, Y.; Lian, W.; Liu, Z. Analyst 2011, 136, 2139. doi: 10.1039/c0an00933d
[11]	Zhang, M.; Xiao, H.; Han, Z.; Yang, L.; Wu, X. Chin. J. Org. Chem. 2018, 38, 926 (in Chinese). doi: 10.6023/cjoc201708061
	(张敏, 肖慧丰, 韩志湘, 杨柳青, 吴向阳, 有机化学, 2018, 38, 926.) doi: 10.6023/cjoc201708061
[12]	(a) Acharyya, S.; Gharami, S.; Patra, L.; Mondal, T. K. J. Fluoresc. 2017, 27, 2051. doi: 10.1007/s10895-017-2144-9 pmid: 28823086
[5]	(何佳伟, 解正峰, 薛松松, 刘宇程, 石伟, 陈鑫, 有机化学, 2021, 41, 2839.) doi: 10.6023/cjoc202102013
	(d) Wu, M.; Yu, Y.; Liu, Y.; You, J.; Wu, W.; Liu, B. Chin. J. Org. Chem. 2022, 42, 803 (in Chinese).
	(吴绵园, 喻艳超, 刘洋, 由君, 武文菊, 刘波, 有机化学, 2022, 42, 803.) doi: 10.6023/cjoc202109049
	(e) Fang, R.; Ding, X.; Luo, W.; Hong, C. Chin. J. Org. Chem. 2020, 40, 2949 (in Chinese). doi: 10.6023/cjoc202004007
	(房茹, 丁旭, 罗稳, 洪琛, 有机化学, 2020, 40, 2949.) doi: 10.6023/cjoc202004007
	(f) Bhardwaj, V.; Hindocha, L.; Kumar, S. A.; Sahoo, S. K. New J. Chem. 2022, 46, 3257.
[12]	(b) Wang, L.; Li, W.; Zhi, W.; Ye, D.; Wang, Y.; Ni, L.; Bao, X. Dyes Pigm. 2017, 147, 357. doi: 10.1016/j.dyepig.2017.07.021 pmid: 28823086
[13]	Yuan, L.; Lin, W.; Song, J.; Yang, Y. Chem. Commun. 2011, 47, 12691. doi: 10.1039/c1cc15762k
[14]	Williams, A. T. R.; Winfield, S. A.; Miller, J. N. Analyst 1983, 108, 1067. doi: 10.1039/an9830801067
[5]	(g) Zha, B.; Fang, S.; Chen, H.; Guo, H.; Yang, F. Spectrochim. Acta, Part A 2022, 269, 120765. doi: 10.1016/j.saa.2021.120765
	(h) Cheng, X.; Zhang, R.; Sun, J.; Xu, K.; Li, W. J. Fluoresc. 2025, 35, 89. doi: 10.1007/s10895-023-03492-w
	(i) Meng, X.; Zhao, J.; Ma, W. Chin. J. Org. Chem. 2020, 40, 276 (in Chinese). doi: 10.6023/cjoc201908039
	(孟宪娇, 赵晋忠, 马文兵, 有机化学, 2020, 40, 276.) doi: 10.6023/cjoc201908039
	(j) Mishra, S. K.; Dehuri, S.; Bag, B. Org. Biomol. Chem. 2020, 18, 316. doi: 10.1039/C9OB02439E

[1]	彭澳霈, 李扬, 朱园园, 吴广文, 古双喜. 席夫碱型荧光探针对氨基酸化学选择性识别研究进展[J]. 有机化学, 2025, 45(9): 3301-3313.
[2]	李兆周, 谢亚芳, 陶健, 魏雪冰, 黎乐乐, 李亚娟, 唐嘉敏, 牛华伟, 陈秀金, 高红丽, 李芳, 于慧春, 袁云霞, 古绍彬, 康怀彬, 孙晓菲, 任国艳, 吴影. 半胱氨酸荧光探针的构建及其在病理学检验中的应用[J]. 有机化学, 2025, 45(7): 2335-2349.
[3]	沈晴, 曾玉, 黎忠昊, 曹西颖, 郭玉婷, 叶蕴仪, 汪朝阳. 基于共价键形成与切断的反应型小分子荧光探针的研究进展[J]. 有机化学, 2025, 45(4): 1194-1205.
[4]	张文博, 苏思铭, 杨鹏. 新型杯[3]咔唑衍生物的合成及其对羟喜树碱识别与检测研究[J]. 有机化学, 2025, 45(4): 1395-1401.
[5]	相韩悦, 魏少荫, 王玉记, 肖猱. 基于N-氧化物结构Fe^2＋荧光探针的研究进展[J]. 有机化学, 2025, 45(4): 1137-1152.
[6]	陈冰燕, 孙洁, 熊玲红, 何学文. 非典型核酸结构的荧光点亮成像检测[J]. 有机化学, 2025, 45(11): 4082-4107.
[7]	曾玉, 黎忠昊, 邓思威, 陈祖佳, 陈璧瑜, 宇世伟, 沈晴, 汪朝阳. 氰基乙烯类化合物的制备与应用研究进展[J]. 有机化学, 2024, 44(9): 2722-2731.
[8]	何春, 刘姝祺, 成奋民, 郝远强, 陈述, 张培盛, 曾荣今. 具有双态发光性质的双光子丹磺酰类荧光探针的合成及其在硫化氢检测中的应用研究[J]. 有机化学, 2024, 44(9): 2869-2875.
[9]	苏小龙, 李健鹏, 刘孟鑫, 邹莉, 杨得锁, 冯海涛. 四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu^2＋[J]. 有机化学, 2024, 44(8): 2581-2587.
[10]	胡亦然, 张巳亮, 罗海艳, 赵璐瑶, 郭旭东, 王双青, 胡睿, 杨国强. 新型查尔酮衍生物氨肽酶N荧光探针的设计及应用[J]. 有机化学, 2024, 44(7): 2257-2264.
[11]	李非凡, 余康, 倪传志, 朱园园, 曾婕, 古双喜. 测定氨基酸浓度和对映体组成的手性荧光探针[J]. 有机化学, 2024, 44(6): 1862-1869.
[12]	刘琳, 陈琳, 胡晓玲, 钟克利, 张璟琳, 汤立军. 基于苯并吡喃点亮型硫化氢荧光探针在食品检测中的应用与细胞成像[J]. 有机化学, 2024, 44(6): 2027-2032.
[13]	张文艳, 王丹, 罗仁洁, 刘会玲. 近红外荧光手术导航探针的研究进展[J]. 有机化学, 2024, 44(6): 1760-1776.
[14]	徐冬青, 童海姗, 沈杰, 邱万伟, 钱立生. 脂滴特异性荧光探针的构建及可视化肝肿瘤细胞[J]. 有机化学, 2024, 44(4): 1240-1246.
[15]	程晓红, 刘发龙, 孙进博, 张锐. 一种用于次氯酸根实时高灵敏度检测的络合物基荧光探针[J]. 有机化学, 2024, 44(4): 1284-1292.

基于催化反应的荧光探针及其在气体发生剂中铜含量的检测应用

A Novel Catalytic Fluorescent Probe and Its Application in Copper Detection in Gas-Generating Agents

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 6

参考文献 5

相关文章 15

编辑推荐

相关统计

本文评价