Colorimetric detection of Hg2+ and CH3Hg+ by a novel spirooxazine derivative as a highly sensitive and selective probe

Pattaweepaiboon, Supak; Nanok, Tanin; Kaewchangwat, Narongpol; Suttisintong, Khomson; Sirisaksoontorn, Weekit

doi:10.1016/j.dyepig.2020.108996

Cited by 16 publications

(4 citation statements)

References 48 publications

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“…同样地, 具有螺环结构的荧光素 [117] 、螺噁嗪 [118] 类分子, 也可通过开环-配位反应来检测 Hg 2 ＋ . 例如, Ali 课题组 [119] 先在荧光素结构中引入酰肼基团, 再通过席夫碱反应合成了一种新型 Hg 2 ＋探针 19 (Eq.…”

Section: 开环反应类断键型小分子探针unclassified

Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules

Li,

Chen,

Chen

et al. 2023

Chinese Journal of Organic Chemistry

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Mercury has strong biological toxicity and poses great harm to human health and the environment. Fluorescent probes have been widely applied in the detection of mercury ion in recent years, due to these probes with high sensitivity, high selectivity, and real-time monitoring. Owing to the advantages of small molecules such as structural diversity, good repeatability, easy modification, and clear sensing mechanisms, many organic small molecular fluorescence probes for detecting mercury ion have also been developed. According to the different reaction mechanisms between probes and mercury ion, these organic small molecular fluorescence probes can be classified into two categories based on coordination type reactions and bond breaking type reactions. The research progress of organic small molecular fluorescence probes used to detect mercury ion in the past five years is summarized in detail. This provides a reference for their further development in the future, especially for the new turn-on type reactive organic small molecular fluorescence probes for detecting mercury ion by utilizing the characteristic reactions. Keywords mercury ion detection; fluorescent probes; organic small molecules; reaction mechanism; molecular design and synthesis 汞是一种剧毒的不可降解的金属污染物 [1] , 一旦进入生物体, 就会在生物体内累积, 影响蛋白质和酶的正常功能, 进而导致各种急性中毒事件 [2] . 因此, 建立一种灵敏、选择性检测汞离子的有效分析方法, 对汞离子的监测、临床诊断及治疗具有重要意义 [3] . 与用来检测汞离子的传统分析方法, 如伏安法、原子吸收光谱法、 X 射线吸收光谱法、分光光度法等相比, 荧光探针具有高选择性、响应速度快和可实时监测等优点 [4] . 这使得汞离子荧光探针引起了研究人员极大的关注, 并得到了高速发展 [5][6][7] .

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Section: 开环反应类断键型小分子探针unclassified

Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules

Li,

Chen,

Chen

et al. 2023

Chinese Journal of Organic Chemistry

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“…As a class of powerful candidates for excellent optical probes, organic conjugated small molecules with electron donor-π-acceptor (D-π-A) architectures have been the focus of attention and research [ 10 , 11 , 12 , 13 , 14 ]. Among them, indole, triphenyl boride [ 15 , 16 , 17 ], rhodamine [ 18 , 19 ], and coumarin [ 20 , 21 , 22 ] have been reported frequently.…”

Section: Introductionmentioning

confidence: 99%

A Novel Indole Derivative with Superior Photophysical Performance for Fluorescent Probe, pH-Sensing, and Logic Gates

Liu

Zhan

Zhong

et al. 2023

IJMS

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An indole-related molecules have been considered as the potential fluorescent probes for biological and electrochemical sensing. However, most of the indole probes have been usually used in a single detection mode. Indolium probes that enable accurate detection in complex environments are rarely reported. Here, four novel indole derivatives including the phenyl group substituted with different functional moieties were designed on the basis of the donor-π-acceptor (D-π-A) concept. These derivatives exhibit positive solvatochromism owing to their varied molecular conformations upon contacting to various solvents and the different HOMO-LUMO gaps caused by the difference in electronic push-pull capability of the substituents. Their solid-state fluorescence emissions and multiple chromisms are observed due to the inherent twisted geometries and aggregation modes. In addition, these derivatives show dramatic color and fluorescence responses due to the protonation of the nitrogen and oxygen containing groups, and thus novel colorimetric pH sensors, fluorescent papers and logic gates have been designed.

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“… 46 Recently, some spirooxazine probes showed high selectivity for the detection of metal ions, including Mg 2+ , Al 3+ , Fe 3+ , Co 2+ , Zn 2+ , Hg 2+ , and CH 3 Hg + . 47 − 53 However, few studies of spirooxazine probes for Cu 2+ detection have been described, and to the best of our knowledge, the spirooxazine as a dual probe for Cu 2+ and Fe 3+ detection has not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

“…Typically, the ring-opening reaction of spirooxazine proceeds through bond cleavage at the spiro carbon (C spiro –O), which is induced by either electromagnetic radiation or metal ion stimuli. , This process results in the formation of an open-ring form, also known as merocyanine, which can serve as an active ligand to selectively coordinate with a metal ion and produce a merocyanine–metal complex . Recently, some spirooxazine probes showed high selectivity for the detection of metal ions, including Mg 2+ , Al 3+ , Fe 3+ , Co 2+ , Zn 2+ , Hg 2+ , and CH 3 Hg + . − However, few studies of spirooxazine probes for Cu 2+ detection have been described, and to the best of our knowledge, the spirooxazine as a dual probe for Cu 2+ and Fe 3+ detection has not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu²⁺ and Fe³⁺ and Its Application in Drinking Water and Rice Quality Monitoring

et al. 2022

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A spirooxazine derivative, PheSPO (3,3-dimethyl-1-phenethylspiro[indoline-2,3′-naphtho[2,1- b ][1,4]oxazine]), as a dual-sensing probe for Cu 2+ and Fe 3+ was synthesized, and its structure was confirmed by 1 H NMR, 13 C NMR, HRMS, and single-crystal X-ray diffraction. The results reveal that the PheSPO probe is selective to both Cu 2+ and Fe 3+ through distinct colorimetric responses in acetonitrile. The sensing performance of PheSPO toward Cu 2+ was investigated, and upon addition of Cu 2+ , an instant change in color from colorless to bright yellow with a strong absorption band at 467 nm was observed. Due to a dual-sensing behavior, PheSPO also exhibits a unique response toward Fe 3+ that can be discovered from a color change from colorless to red at an absorption wavelength of 514 nm. Based on spectroscopic analyses and density functional theory calculations, the 1:1 stoichiometric complexation of PheSPO with the targeted metal ions was proposed and the binding constants of 1.95 × 10 3 M –1 for Cu 2+ and 1.29 × 10 3 M –1 for Fe 3+ were obtained. In addition, the detection limits of PheSPO for Cu 2+ and Fe 3+ were 0.94 and 2.01 μM, respectively. To verify its applicability in real samples, PheSPO was further explored for quantitative determination of both Cu 2+ and Fe 3+ in spiked drinking water. The results showed that the recoveries of Cu 2+ and Fe 3+ examined using the PheSPO probe were found comparable to those obtained from atomic absorption spectroscopy. Moreover, the PheSPO strip test was developed, and its utilization for qualitative detection of Fe 3+ in real rice samples was demonstrated.

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Colorimetric detection of Hg2+ and CH3Hg+ by a novel spirooxazine derivative as a highly sensitive and selective probe

Cited by 16 publications

References 48 publications

Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules

Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules

A Novel Indole Derivative with Superior Photophysical Performance for Fluorescent Probe, pH-Sensing, and Logic Gates

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu²⁺ and Fe³⁺ and Its Application in Drinking Water and Rice Quality Monitoring

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Colorimetric detection of Hg2+ and CH3Hg+ by a novel spirooxazine derivative as a highly sensitive and selective probe

Cited by 16 publications

References 48 publications

Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules

Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules

A Novel Indole Derivative with Superior Photophysical Performance for Fluorescent Probe, pH-Sensing, and Logic Gates

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu2+ and Fe3+ and Its Application in Drinking Water and Rice Quality Monitoring

Contact Info

Product

Resources

About

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu²⁺ and Fe³⁺ and Its Application in Drinking Water and Rice Quality Monitoring