A highly selective A–π–A “turn-on” fluorescent probe for hypochlorite in tap water

Abstract

A highly selective fluorescence probe (BON) for hypochlorite (ClO-) was designed and synthesized. The probe was based on boron-dipyrromethene (BODIPY) dye as the fluorophore and diaminomaleonitrile (DAMN) as the recognition...

A Near-Infrared Fluorescent Probe for Recognition of Hypochlorite Anions Based on Dicyanoisophorone Skeleton

“…In addition, the fluorescence probing method was paid more attention as an excellent detection tool, which has realized the detection of many active species [ 19 , 20 , 21 , 22 , 23 ]. Fluorescence probes for the detection of hypochlorite anions have been reported continuously in recent years [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 ]. Among them, some chemodosimeters using a diaminomaleonitrile group as the reaction site were used to detect hypochlorite anions, which had many advantages, such as specific recognition, high selectivity, and fast response.…”

“…Among them, some chemodosimeters using a diaminomaleonitrile group as the reaction site were used to detect hypochlorite anions, which had many advantages, such as specific recognition, high selectivity, and fast response. However, most chemodosimeters for the hypochlorite anion could hardly achieve near-infrared fluorescence emission and did not have a large Stokes shift ( Table S1 ) [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 ]. It is well known that NIR fluorescent probes with a large Stokes shift have more advantages due to good applications in biological systems [ 47 ].…”

A ratiometric near‐infrared fluorescent probe for the detection and monitoring of hypochlorous acid in rheumatoid arthritis model and real water samples

“…[10] In addition, HOCl is usually used as an high-efficiency disinfectant and bleach to pretreat tap water and treat industrial wastewater or industrial bleaching. [11] But excessive discharge of HOCl can cause serious damage to the ecological environment and high-dose intake can also cause some fatal diseases. [12][13][14] Accordingly, to develop high-efficiency and accurate techniques for the detection and monitoring of HOCl in vivo has important meanings and value in the thorough understanding of the role of HOCl in RA as well as assessing the efficacy of drug therapy for HOCl-associated diseases.…”

“…Compared with other detection techniques, fluorescent imaging technique has gradually developed into a promising imaging method on account of its unique advantages of high sensitivity, excellent spatiotemporal resolution, outstanding biocompatibility, and real-time imaging, etc. [15][16][17][18][19][20] Up to now, numerous fluorescent probes based on diverse response mechanisms have been developed, including HOClinduced oxidation reaction with C=C double bond, [21,22] C=N double bond, [10,11,23] oxime, [24,25] p-methoxyphenol, [26] p-alkoxyaniline, [27,28] arylmethylsulfide, [29][30][31] N,N-dimethylthiocarbamate, [32][33][34][35] the spirocyclic hydrazide group, [36,37] arylboric acid and arylboric acid pinacol ester, [38,39] and S atom of phenothiazine. [40][41][42] Nevertheless, most of the previously developed HOCl fluorescent probes still suffer from several problems, including shorter emission wavelengths, [11,24,27] poorer water solubility, [10,43] and smaller Stokes shifts, [6,11] which restrict their applications in biological systems and real water samples.…”

A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid

“…The following supporting information can be downloaded at: , Figures S1, S3, S5 and S8: 1 H NMR spectra of HTCP, NTC, HTCP-NTC and HTCP-OH; Figures S2, S4, S6 and S9: 13 C NMR spectra of HTCP, NTC, HTCP-NTC and HTCP-OH; Figures S7 and S10: HRMS of HTCP-NTC and HTCP-OH; Figure S11: Fluorescence emission spectra of HTCP-NTC with HOCl at different pH; Figure S12: The pKa measurement of HTCP-OH; Figure S13: The absorption and fluorescence changes for HTCP-NTC and HTCP-OH in various viscosity; Figure S14: The absorption and fluorescence changes for HTCP-NTC and HTCP-OH in solvents of different polarity; Figure S15: HPLC analysis of HTCP-NTC response with HOCl; Figure S16: The absorption, fluorescence emission and excitation spectra of HTCP-OH and the reaction mixtures for HTCP-NTC with HOCl; Figure S17: The cell viability of RAW264.7 after 24 h incubation with HTCP-NTC; Table S1: The summary of photophysical properties of reported similar probes. References [ 59 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 ] are cited in the Supplementary Materials.…”