高选择和高灵敏检测溶液和气相中硫化氢的新型萘酰亚胺类开启型荧光探针

doi:10.6023/cjoc202305002

摘要/Abstract

构建了一种用于硫化氢检测的新型萘酰亚胺类开启型荧光探针(NPHQ). 因硫化氢亲核效应促使NPHQ中萘醌结构离解, 导致探针分子中的光诱导电子转移(PET)效应消失和萘酰亚胺分子内电荷转移(ICT)效应恢复, 而呈现出强烈的荧光开启效应. NPHQ荧光强度对0~0.5 μmol/L硫化氢呈线性增强, 检测限为1.68 nmol/L. NPHQ具备的高选择性、高灵敏度和荧光开启响应, 使其在溶液和气相中检测硫化氢, 具有较好的应用前景和价值.

关键词: 硫化氢, 荧光探针, 开启型, 萘酰亚胺, 溶液和气相

A novel turn-on fluorescent probe (NPHQ) based on naphthalimide had been constructed to detect hydrogen sulfide. The nucleophilic effect of hydrogen sulfide induced the decomposition of naphthoquinone structure, which resulted in the disappearance of photo-induced electron transfer (PET) of NPHQ and recovery of intramolecular charge transfer (ICT) of naphthalimide. The fluorescence intensities of NPHQ showed a linear enhancement response to hydrogen sulfide in the concentration range of 0~0.5 μmol/L with limit of detection of 1.68 nmol/L. Moreover, NPHQ held promising application prospects for detecting hydrogen sulfide in solution and gas based on its high selectivity, sensitivity and specific turn-on emission.

Key words: hydrogen sulfide, fluorescence probe, turn-on, naphthalimide, solution and gas

引用此文

周五, 彭敏, 梁庆祥, 吴爱斌, 舒文明, 余维初. 高选择和高灵敏检测溶液和气相中硫化氢的新型萘酰亚胺类开启型荧光探针[J]. 有机化学, 2023, 43(12): 4277-4283.

Wu Zhou, Min Peng, Qingxiang Liang, Aibin Wu, Wenming Shu, Weichu Yu. A Novel Turn-On Fluorescent Probe Based on Naphthalimide for Highly Selective and Sensitive Detection of Hydrogen Sulfide in Solution and Gas[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4277-4283.

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图/表 6

Scheme 1. Synthetic route of NPHQ

Figure 1. Fluorescence response of NPHQ (10 μmol/L) against different interfering analytes (100 μmol/L)

Figure 2. (a) Absorption and emission spectra of NPHQ (10 μmol/L) in DMSO/H2O (V/V=1/9) solution in absence and presence of H2S (100 μmol/L) (inset: the fluorescence color of NPHQ in absence and presence of H2S under 365 nm fluorescent lamp); (b) fluorescence intensity changes of NPHQ (10 μmol/L) in DMSO/H2O (V/V=1/9) solution with the addition of H2S (0~0.5 μmol/L) (inset: linear relationship between the fluorescence intensity of NPHQ and the concentration of H2S)

Figure 3. Fluorescence intensities of NPHQ (10 μmol/L) in the presence of 100 μmol/L interfering species including H2S, Mn2+, Al3+, Sn4+, K+, Cr3+, Ca2+, Zn2+, Na+, Ba2+, Ce3+, Mg2+, I–, ${{\text{S}}_{2}}\text{O}_{5}^{2-}$, $\text{HCO}_{3}^{-}$, $\text{MnO}_{\text{4}}^{-}$, $\text{HSO}_{3}^{-}$, $\text{SO}_{\text{4}}^{2-}$, $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$, H2- $\text{PO}_{4}^{-}$, $\text{CO}_{3}^{2-}$, Br–, $\text{ClO}_{3}^{-}$, $\text{NO}_{2}^{-}$, ClO–, H2O2, GSH, Cys, Hcy, DTT and βME (λex=390 nm)

Figure 4. Proposed recognition mechanism of NPHQ to H2S

Figure 5. Test strips for detection of H2S gas (0, 38, 76, 152, 228, 301, 455, 607 mg/m3 ) under fluorescent lamp λex=365 nm. Pictures were taken after exposure to H2S gas for 10 s

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