Synthesis of Two-Photon Dansyl-Based Fluorescent Probe with Dual-State Emission Properties for Hydrogen Sulfide Detection

doi:10.6023/cjoc202402010

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2869-2875.DOI: 10.6023/cjoc202402010 Previous Articles Next Articles

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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

何春, 刘姝祺, 成奋民, 郝远强, 陈述, 张培盛^*(), 曾荣今^*()

湖南科技大学化学化工学院湖南湘潭 411201

收稿日期:2024-02-20 修回日期:2024-04-10 发布日期:2024-05-10
通讯作者: 张培盛, 曾荣今
基金资助:
国家自然科学基金(52273290); 国家自然科学基金(52173278); 国家自然科学基金(52073087); 湖南省自然科学基金(2024JJ2033); 湖南省科技创新计划(2022RC1075)

Synthesis of Two-Photon Dansyl-Based Fluorescent Probe with Dual-State Emission Properties for Hydrogen Sulfide Detection

Chun He, Shuqi Liu, Fenmin Cheng, Yuanqiang Hao, Shu Chen, Peisheng Zhang(), Rongjin Zeng()

School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201

Received:2024-02-20 Revised:2024-04-10 Published:2024-05-10
Contact: Peisheng Zhang, Rongjin Zeng
Supported by:
National Natural Science Foundation of China(52273290); National Natural Science Foundation of China(52173278); National Natural Science Foundation of China(52073087); Natural Science Foundation of Hunan Province(2024JJ2033); Science and Technology Innovation Program of Hunan Province(2022RC1075)

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Abstract

Hydrogen sulfide (H₂S) is a kind of irritant and volatile environmental toxic gas. It is also an important functional small molecule in organisms. Therefore, it is very important to develop fluorescent probes that can detect H₂S in different states (such as solution and gas). In this study, a dansyl-based fluorophore (DNs) with dual-state emission (DSE) properties and high fluorescence quantum yields was successfully synthesized. Furthermore, a 2,4-dinitrobenzenesulfonyl moiety was introduced to synthesize a fluorescent probe, DNs-HPP-DNBS, for H₂S detection. Leveraging the DSE properties of DNs, the DNs-HPP-DNBS probe not only achieved sensitive detection of H₂S in solution, with a detection limit of 1.16 μmol•L^－1. At the same time, it can monitor gaseous H₂S after loading on solid substrate. In addition, its two-photon performance is expected to play its good application potential in biology and cell imaging.

Key words: dual-state emission, two-photon, fluorescent probe, hydrogen sulfide

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Chun He, Shuqi Liu, Fenmin Cheng, Yuanqiang Hao, Shu Chen, Peisheng Zhang, Rongjin Zeng. Synthesis of Two-Photon Dansyl-Based Fluorescent Probe with Dual-State Emission Properties for Hydrogen Sulfide Detection[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2869-2875.

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Fig. & Tab. 10

Scheme 1. Synthesis of DNs-HPP and DNs-HPP-DNBS

Figure 1. Normalized fluorescence emission spectra of DNs- HPP in solution (THF) and in solid state Ex=350 nm, the inset is an image of DNs-HPP illuminated by 365 nm ultraviolet lamp

Figure 2. Fluorescence emission spectra of DNs-HPP in THF (Ex=760 nm)

Figure 3. Fluorescence spectra of DNs-HPP-DNBS before and after reaction with H2S Ex=350 nm, the inset is an image of DNs-HPP illuminated by 365 nm ultraviolet lamp

Scheme 2. Proposed sensing mechanism of DNs-HPP-DNBS toward H2S

Figure 4. Fluorescence spectra of DNs-HPP-DNBS in the presence of H2S (0~50 μmol?L－1)

Figure 5. Fluorescent response of DNs-HPP-DNBS to different species

Figure 6. Effect of H2S on DNs-HPP-DNBS in the presence of different interferent

样品	H₂S加入量/ (μmol•L^－1)	H₂S检出量^a/(μmol•L^－1)	RSD/% (n=3)	回收率/ %
自来水	0	—	—	—
	10.00	9.89	1.39	98.90
	20.00	19.93	1.36	99.70
明湖水	0	—	—	—
	10.00	9.90	6.30	99.00
	20.00	20.02	1.39	100.1

Table 1. Detection of H2S in tap water and lake water

Figure 7. Images of cotton stained with probe DNs-HPP-DNBS at different H2S concentrations under ultraviolet light irradiation

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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

Synthesis of Two-Photon Dansyl-Based Fluorescent Probe with Dual-State Emission Properties for Hydrogen Sulfide Detection

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