Benzimidazole-Derived Fluorescence Enhancement Probe for Visual Detection of HClO †

doi:10.7503/cjcu20190366

Abstract

Abstract:

A novel benzimidazole-derived fluorescence enhancement probe 2-{[4-(1H-benzo[d]imidazol-2-yl)benzylidene]amino}-3-aminoma-leonitrile(ZY12) was synthesized, and its recognition of HClO was researched with spectral methods. The results showed that ZY12 demonstrated relatively high selectivity and sensitivity to ClO ^-. It had quick response and strong anti-interference ability. Upon addition of ClO ^- to ZY12 solution, the fluorescence intensity of reaction system increased with the increasing concentration of ClO ^-, accompanied with fluorescence color change from faint blue to bright blue, realizing the visual detection of ClO ^-. ZY12 could quantitatively detect ClO ^- at concentrations ranging from 1.8×10 ^-6—3.4×10 ^-5 mol/L with a detection limit of 2.8×10 ^-7 mol/L. ZY12 was used to determine ClO ^- in various water samples, and it could also be applied to intracelluar ClO ^- imaging in living HeLa cells.

Key words: Hypochlorous acid, Fluorescent probe, Visual detection, Fluorescence imaging

CLC Number:

O657
O626.23

TrendMD:

Yong ZHANG,Cheng SHEN,Zhirong XING,Guiqi CHEN,Zi LU,Zhibing HOU,Xuemei CHEN. Benzimidazole-Derived Fluorescence Enhancement Probe for Visual Detection of HClO ^†[J]. Chem. J. Chinese Universities, 2019, 40(12): 2480.

Figures/Tables 10

Scheme 1 Synthesis of the probe ZY12

Fig.1 Fluorescent response of ZY12(10 μmol/L, a) to different analytes(30 μmol/L, b—p) Analyte: b. F-; c. Cl-; d. Br-; e. I-; f. Ac-; g. C$O_{3}^{2-}$; h.$N_{3}^{-}$; i. N$O_{2}^{-}$; j. N$O_{3}^{-}$; k. S2-; l. S$O_{3}^{2-}$; m. SCN-; n. t-BuOOH; o. H2O2; p. ClO-.

Fig.2 Effect of ClO- on ZY12(10 μmol/L) in the presence of different interferents(100 μmol/L) Interferent: a. F-; b. Cl-; c. Br-; d. I-; e. Ac-; f. C$O_{3}^{2-}$; g.$NO_{3}^{-}$; h. N$O_{2}^{-}$; i. N$O_{3}^{-}$; j. SCN-; k. S2-; l. S$O_{3}^{2-}$; m. t-BuOOH; n. H2O2.

Fig.3 Fluorescence intensity changes of ZY12(10 μmol/L) upon gradual addition of ClO-(0—30 μmol/L) The inset shows the linear relationship between the fluorescence intensity of ZY12 and concentrations of ClO-.

Fluorescent probe	λ_ex/λ_em(nm)	Solvent	Detection limit/(μmol·L^-1)	Ref.
HQ	370/495	PBS/DMSO(volume ratio 1:9)	0.31	[18]
1b	398/455	PBS/CH₃CN(volume ratio 8:2)	0.36	[19]
L1	405/505	PBS	0.67	[20]
BDP-OX	488/538, 589	PBS/DMSO(volume ratio 1:9)	0.85	[21]
HA	340/460, 570	PBS/DMF(volume ratio 99:1)	0.70	[22]
ZY12	322/472	EtOH/H₂O(volume ratio 1:9)	0.28	This work

Fig.4 Time-dependent fluorescence intensity changes of ZY12(10 μmol/L) in the presence of ClO-(30 μmol/L) The inset shows the fluorescence color of ZY12 before(left) and after(right) addition of ClO- under UV light(365 nm).

Fig.5 Fluorescence intensity vs. pH values of ZY12(10 μmol/L) in the absence and presence of ClO-(30 μmol/L)

Fig.6 Proposed mechanism of the response of probe ZY12 towards ClO-

Water sample	ClO^- added/(μmol·L^-1)	ClO^- found/(μmol·L^-1)	Recovery(%)	RSD(%)
Tap water	10.0	9.60	96.0	3.8
	20.0	19.30	96.5
	30.0	30.81	102.7
Mineral water	10.0	9.71	97.1	3.0
	20.0	19.52	97.5
	30.0	30.73	102.3
Changjiang river water	10.0	10.32	103.2	4.7
	20.0	19.10	95.5
	30.0	31.29	104.3

Fig.7 Bright-field(A, C) and fluorescence(B, D) images of HeLa cells treated with probe ZY12(10 μmol/L)(A, B) and treated with probe ZY12(10 μmol/L) and NaClO (50 μmol/L) for 30 min(C, D)

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