Research Progress of Reaction-Based Probes for Detecting Fluoride Ion

doi:10.6023/cjoc202302015

Abstract

Fluoride ion is closely related to human life activities. Excessive or too little fluoride ions in human body will cause pathological changes. Therefore, it is necessary to develop appropriate measures to detect the fluoride ion content in human body and environment. Colorimetry and fluorescence detection have attracted much attention due to their high selectivity, high sensitivity and fast response. Herein, reaction-based fluoride ion probes are introduced. According to the reaction mechanisms, these probes can be divided into five types: interactions between fluoride ion and boronic acid derivatives, fluoride ion-promoted cleavage of Si—C bond, fluoride ion-promoted cleavage of Si—O bond, fluoride ion-induced dehydrogenation, fluoride ion-promoted cleavage of P—O bond. Not only the detection method of the probe is introduced, but also the action mechanism of some examples is described.

Key words: fluoride ion, colorimetric and fluorescent detection, reaction-based probe, bio-imaging, environmental detection

Cite this article

Yanjie Qu, Yajun Li, Hongli Bao. Research Progress of Reaction-Based Probes for Detecting Fluoride Ion[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 809-825.

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Fig. & Tab. 36

Scheme 1. Mechanism of boric acid probe for detecting fluoride ion

Scheme 2. Mechanism of probe 1 for detecting fluoride ion and structures of other organic borate probes for detecting fluoride ion

Scheme 3. Mechanism of probe 9 for detecting fluoride ion

Scheme 4. Mechanism of probe 10 for detecting fluoride ion

Scheme 5. Mechanism of probe 11 for detecting fluoride ion

Scheme 6. Mechanism of probe 12 for detecting fluoride ion

Scheme 7. Mechanism of probe 13 for detecting fluoride ion

Scheme 8. Mechanism of probe 14 for detecting fluoride ion

Scheme 9. Mechanism of probe 15 for detecting fluoride ion and structures of probes 16~18

Scheme 10. Mechanism of probe 19 for detecting fluoride ion

Scheme 11. Mechanism of probe 21 for detecting fluoride ion

Scheme 12. Mechanism of probe 23 for detecting fluoride ion

Scheme 13. Mechanism of probe 24 for detecting fluoride ion

Figure 1. (a) Confocal fluorescence images of HepG2 cells and (b) representative fluorescence images of BALB/c mice (pseudocolor)[23]Copyright {2018} American Chemistry Society. Copyright {2018} American Chemistry Society.

Scheme 14. Mechanism of probe 26 for detecting fluoride ion

Scheme 15. Mechanism of probe 27 for detecting fluoride ion

Figure 2. (a) Probes colocalizes to mitochondria and lysosome in HeLa cells and (b) representative fluorescence images of Mito-F in mice[26] Copyright {2015} American Chemistry Society.

Scheme 16. Mechanism of probe 28 for detecting fluoride ion

Scheme 17. Mechanisms of probes 31, 32 and 33 for detecting fluoride ion

Scheme 18. Mechanisms of probe 34 for detecting fluoride ion

Scheme 19. Mechanisms of probes 35 and 36 for detecting fluoride ion

Scheme 20. Mechanisms of probes 37, 38, and 39 for detecting fluoride ion

Scheme 21. Mechanisms of probes 40, 41, 42 and 43 for detecting fluoride ion

Scheme 22. Mechanism of probe 44 for detecting fluoride ion

Scheme 22. Mechanism of probe 45 for detecting fluoride ion

Scheme 24. Mechanisms of probes 46 and 47 for detecting fluoride ion

Scheme 25. Mechanisms of probes 48, 49 and 50 for detecting fluoride ion

Scheme 26. Mechanism of probe 51 for detecting fluoride ion

Figure 3. (a) Emission spectra of 51 in DCM upon the addition of 0~2.0 μmol/L TBAF and (b) plot of the emission intensity of 51 between 635 and 563 nm (I635 nm/I563 nm) vs concentration of F– in dichloromethane (DCM)[50] Copyright {2010} American Chemistry Society.

Scheme 27. Mechanisms of probes 52, 53 and 54 for detecting fluoride ion

Scheme 28. Mechanism of probe 55 for detecting fluoride ion

Scheme 29. Mechanism of probe 56 for detecting fluoride ion

Scheme 30. Mechanism of probe 57 for detecting fluoride ion

Scheme 31. Mechanism of probe 58 for detecting fluoride ion

Scheme 32. Mechanism of probe 59 for detecting fluoride ion

化合物	检测所用溶剂	吸收(A)/发射(E_m)检测波长/nm	响应模式	响应时间	检测极限
13	乙腈	E_m=550	打开型	<2 min	33 nmol/L
14	二氯甲烷	E_m=584	比率型	5 min	—
15	丙酮	A=555; E_m=571	比色型	5 min	67.4 nmol/L
19	四氢呋喃	E_m=423	比色型	<20 s	53 μmol/L
21	四氢呋喃/十六烷基三甲基溴化铵 (CTAB)水溶液(V∶V=1∶10)	E_m=418, 560	比色型	200 s	≈5.3 μmol/L
22	二甲基亚砜	E_m=472, 606	比率型	—	0.12 μmol/L
23	PBS缓冲液	E_m≈500	打开型	15 min	18 μmol/L
24	PBS缓冲液/二甲基亚砜(V∶V=2∶8)	E_m=690, 780	比率型	15 min	0.2 μmol/L
25	乙腈	E_m=773	猝灭型	Few seconds	—
26	乙腈/水(V∶V=1∶1)	E_m=591	打开型	—	—
27	HEPES缓冲液	E_m=475, 540	比率型	—	Mito-F: 3.5 μmol/L Lyso-F: 3.8 μmol/L
28	二甲基亚砜/HEPES缓冲液(V∶V=1∶1)	E_m=450	打开型	—	670 nmol/L
29	二甲基亚砜	E_m≈450	打开型	—	140 nmol/L
30	乙腈	E_m=748	打开型	90 min	3.2 μmol/L
31	PBS缓冲液/二甲基亚砜(V∶V=1∶9)	E_m=466	打开型	—	47 μmol/L in DMSO 0.67 mmol/L in DMSO/ aqueous buffer mixture
32	Tris缓冲液	E_m=540	打开型	—	0.91 μmol/L
33	水/二甲基亚砜(V∶V=1∶19)	E_m=665	打开型	40 min	157 nmol/L
34	PBS缓冲液	E_m=520	打开型	—	0.38 mg•L^–1
35	二甲基亚砜	E_m=523	打开型	2.41 min	1.03 μmol/L
36	乙腈水缓冲液	E_m=564	打开型	2.5 h	0.59 μmol/L
37	四氢呋喃	E_m=360, 480	比色型	—	1.86 μmol/L
38	乙醇/水(V∶V=1∶1)	E_m=523	打开型	3 min	19.6 nmol/L
39	乙腈/HEPES缓冲液(V∶V=3∶7)	E_m=616	打开型	10 min	5.4 μmol/L
40	二氯甲烷	E_m=458	打开型	—	—
41	四氢呋喃	E_m=403, 502	比率型	10 s	1 μmol/L
42	水/乙腈(V∶V=2∶8)	E_m=407, 477	比率型	—	6.5 μmol/L
43	四氢呋喃	E_m=379	比率型	—	9.7 nmol/L
44	乙腈	E_m=532	打开型	—	—
45	水	E_m=566	打开型	<1 s	0.05 nmol/L
46	二甲基亚砜	E_m=488	猝灭型	—	0.578 μmol/L
47	四氢呋喃	E_m=593	猝灭型	5 s	15 nmol/L
48	乙腈	E_m=485, 590	比率型	—	—
49	乙腈/二甲基亚砜(V∶V=40∶1)	A=400	比色型		2 μmol/L
50	乙腈	E_m=495	打开型		—
51	二氯甲烷	E_m=563, 635	比率型	—	—
52	乙腈	E_m=526	猝灭型	—	—
53	乙腈	A=445, 620	比率比色型	10 s	0.41 μmol/L
54a	二甲基亚砜	E_m=490	猝灭型	—	64 nmol/L
55	乙腈	E_m=443	猝灭型	—	0.52 μmol/L
56	二氯甲烷	A=503, 693	比率比色型	—	0.22 μmol/L
57	二甲基亚砜/Tris缓冲液(V∶V=7∶3)	E_m=536	打开型	10 min	9.8 nmol/L
58	二甲基亚砜/Tris缓冲液(V∶V=7∶3)	E_m=669	猝灭型	6 min	48 nmol/L
59	乙腈	E_m=730	打开型	10 s	4.28 μmol/L

化合物	检测所用溶剂	吸收(A)/发射(E_m)检测波长/nm	响应模式	响应时间	检测极限
13	乙腈	E_m=550	打开型	<2 min	33 nmol/L
14	二氯甲烷	E_m=584	比率型	5 min	—
15	丙酮	A=555; E_m=571	比色型	5 min	67.4 nmol/L
19	四氢呋喃	E_m=423	比色型	<20 s	53 μmol/L
21	四氢呋喃/十六烷基三甲基溴化铵 (CTAB)水溶液(V∶V=1∶10)	E_m=418, 560	比色型	200 s	≈5.3 μmol/L
22	二甲基亚砜	E_m=472, 606	比率型	—	0.12 μmol/L
23	PBS缓冲液	E_m≈500	打开型	15 min	18 μmol/L
24	PBS缓冲液/二甲基亚砜(V∶V=2∶8)	E_m=690, 780	比率型	15 min	0.2 μmol/L
25	乙腈	E_m=773	猝灭型	Few seconds	—
26	乙腈/水(V∶V=1∶1)	E_m=591	打开型	—	—
27	HEPES缓冲液	E_m=475, 540	比率型	—	Mito-F: 3.5 μmol/L Lyso-F: 3.8 μmol/L
28	二甲基亚砜/HEPES缓冲液(V∶V=1∶1)	E_m=450	打开型	—	670 nmol/L
29	二甲基亚砜	E_m≈450	打开型	—	140 nmol/L
30	乙腈	E_m=748	打开型	90 min	3.2 μmol/L
31	PBS缓冲液/二甲基亚砜(V∶V=1∶9)	E_m=466	打开型	—	47 μmol/L in DMSO 0.67 mmol/L in DMSO/ aqueous buffer mixture
32	Tris缓冲液	E_m=540	打开型	—	0.91 μmol/L
33	水/二甲基亚砜(V∶V=1∶19)	E_m=665	打开型	40 min	157 nmol/L
34	PBS缓冲液	E_m=520	打开型	—	0.38 mg•L^–1
35	二甲基亚砜	E_m=523	打开型	2.41 min	1.03 μmol/L
36	乙腈水缓冲液	E_m=564	打开型	2.5 h	0.59 μmol/L
37	四氢呋喃	E_m=360, 480	比色型	—	1.86 μmol/L
38	乙醇/水(V∶V=1∶1)	E_m=523	打开型	3 min	19.6 nmol/L
39	乙腈/HEPES缓冲液(V∶V=3∶7)	E_m=616	打开型	10 min	5.4 μmol/L
40	二氯甲烷	E_m=458	打开型	—	—
41	四氢呋喃	E_m=403, 502	比率型	10 s	1 μmol/L
42	水/乙腈(V∶V=2∶8)	E_m=407, 477	比率型	—	6.5 μmol/L
43	四氢呋喃	E_m=379	比率型	—	9.7 nmol/L
44	乙腈	E_m=532	打开型	—	—
45	水	E_m=566	打开型	<1 s	0.05 nmol/L
46	二甲基亚砜	E_m=488	猝灭型	—	0.578 μmol/L
47	四氢呋喃	E_m=593	猝灭型	5 s	15 nmol/L
48	乙腈	E_m=485, 590	比率型	—	—
49	乙腈/二甲基亚砜(V∶V=40∶1)	A=400	比色型		2 μmol/L
50	乙腈	E_m=495	打开型		—
51	二氯甲烷	E_m=563, 635	比率型	—	—
52	乙腈	E_m=526	猝灭型	—	—
53	乙腈	A=445, 620	比率比色型	10 s	0.41 μmol/L
54a	二甲基亚砜	E_m=490	猝灭型	—	64 nmol/L
55	乙腈	E_m=443	猝灭型	—	0.52 μmol/L
56	二氯甲烷	A=503, 693	比率比色型	—	0.22 μmol/L
57	二甲基亚砜/Tris缓冲液(V∶V=7∶3)	E_m=536	打开型	10 min	9.8 nmol/L
58	二甲基亚砜/Tris缓冲液(V∶V=7∶3)	E_m=669	猝灭型	6 min	48 nmol/L
59	乙腈	E_m=730	打开型	10 s	4.28 μmol/L

Table 1. Performances of probes

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