基于1,8-萘酰亚胺与罗丹明B间荧光共振能量转移的高选择性Hg2+比率荧光探针

doi:10.7503/cjcu20150563

摘要/Abstract

摘要：

以罗丹明B与1,8-萘二甲酰亚胺反应合成了1个高选择性Hg²⁺比率荧光探针(RN). 在甲醇/乙腈/4-羟基哌嗪乙磺酸缓冲溶液(pH=7.2, 体积比8:1:1)中, RN对Hg²⁺具有比色和比率荧光双重响应. 加入Hg²⁺后, RN的紫外-可见光谱在约556 nm处产生强吸收, 溶液由浅绿色变为橙色, 其它金属离子对RN的紫外-可见光谱几乎无影响. 无Hg²⁺存在时, RN的荧光光谱在540 nm处出现萘二甲酰亚胺荧光团的特征峰; 加入Hg²⁺后, 540 nm处的发射带逐渐消失, 同时在580 nm附近产生强荧光, 荧光颜色从绿色变为橙色. 这归因于从萘酰亚胺到开环罗丹明B的荧光共振能量转移(FRET), 探针RN对Hg²⁺的比率荧光响应具有高选择性, 不受其它共存金属离子的干扰.

关键词: 罗丹明B, 1,8-萘二甲酰亚胺, 荧光共振能量转移, Hg²⁺, 比率荧光探针

Abstract:

A ratiometric fluorescent probe(RN) was developed based on rhodamine B and 1,8-naphthalimide which were linked together by an amido linkage. In CH₃OH/CH₃CN/HEPES buffer solution(pH=7.2), free RN showed absorption maximum at 412 nm. The presence of Hg²⁺ could induce an intensive absorption at 556 nm. The change of absorption spectrum resulted in a color change from light green to orange in response to Hg²⁺. Significantly, the probe RN gave rise to a ratiometric fluorescent response to Hg²⁺. Upon the addition of Hg²⁺, a significant fluorescence enhancement at 580 nm and meanwhile the gradual disappearance of the emission at 540 nm were observed, which were ascribed to the fluorescence resonance energy transfer(FRET) from 1,8-naphthalimide moiety to the ring-opened rhodamine B moiety. Accompanying the change of fluorescence spectra, the significant fluorescence color changed from green to orange occurred, which could be used for naked-eye detection of Hg²⁺. The ratiometric fluorescence signal for Hg²⁺ was not affected by other coexisting mental ions.

Key words: Rhodamine B, 1,8-Naphthalimide, Fluorescence resonance energy transfer, Hg²⁺, Ratiometric fluorescent probe

中图分类号:

O657

TrendMD:

陈家逸, 苏伟, 王恩举. 基于1,8-萘酰亚胺与罗丹明B间荧光共振能量转移的高选择性Hg²⁺比率荧光探针. 高等学校化学学报, 2016, 37(2): 232.

CHEN Jiayi, SU Wei, WANG Enju. Highly Selective Ratiometric Fluorescent Probe for Hg²⁺Based on Fluorescence Resonance Energy Transfer Between 1,8-Naphthalimide and Rhodamine B^†. Chem. J. Chinese Universities, 2016, 37(2): 232.

图/表 11

Scheme 1 Synthetic approach for RN

Fig.1 UV-Vis spectra of RN(10 μmol/L) under different conditions (B) Effect of Hg2+ concentration at 556 nm; (C) with different concentrations of Hg2+ (1, 2, 3, 4 and 5 μmol/L) at 556 nm.

Fig.2 UV-Vis spectra(A) and color changes of RN(10 μmol/L)(B) (A) With different metal ions, c(metal ions)=100 μmol/L; (B) addition of Hg2+ under natural light, a. only RN, b. addition of Hg2+(100 μmol/L), c. addition of a mixture of Al3+, Na+, Mn2+, Co2+, Ni2+, Cu2+, Cr3+, Ag+, Pb2+, Zn2+, Cd2+, Fe2+ and Fe3+, each concentration was 100 μmol/L.

Fig.3 Fluorescence spectra of RN(10 μmol/L) (A) c(Hg2+)/(μmol·L-1), a—k: 0, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100. λex=440 nm. Inset: a and b represent colors of RN solution(10 μmol/L) before and after the addition of Hg2+(100 μmol/L) in dark-box ultraviolet analyzer when excited at 365 nm, respectively; (B) fluorescent intensities ratio(I580 nm/I540 nm) as a function of Hg2+ (0, 1, 2, 3 and 4 μmol/L).

Fig.4 Time-dependent ratiometric fluorescence responses of 10 μmol/L RN to 100 μmol/L Hg2+

Fig.5 pH-dependent fluorescence ratios(F580/F540) of RN in the absence(a) and presence(b) of Hg2+

Fig.6 Fluorescence spectra of RN(10 μmol/L) in the presence of various metal ions(100 μmol/L)

Fig.7 Selective responses of RN(10 μmol/L) to Hg2+(100 μmol/L) in the presence of different cations(200 μmol/L) a. None; b. Al3+; c. Na+; d. Mn2+; e. Co2+; f. Ni2+; g. Cu2+; h. Cr3+; i. Ag+; j. Pb2+; k. Zn2+; l. Cd2+; m. Fe3+; n. Fe2+.

Fig.8 ESI-MS of RN in the presence of Hg2+ and trace amounts of Cl- Inset: observed(left) and calculated(right) isotopic patterns for the [RN+Hg+Cl]+.

Scheme 2 Proposed Hg2+-sensing mechanism of RN

Fig.9 Test papers after being sprayed with Hg2+ in water a. None; b. 5.0×10-5 mol/L; c. 1.0×10-4 mol/L; d. 5.0×10-4 mol/L; e. 1.0×10-4 mol/L in filtered lake water.

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基于1,8-萘酰亚胺与罗丹明B间荧光共振能量转移的高选择性Hg²⁺比率荧光探针

Highly Selective Ratiometric Fluorescent Probe for Hg²⁺Based on Fluorescence Resonance Energy Transfer Between 1,8-Naphthalimide and Rhodamine B^†

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