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Review

. 2016 Mar 21;141(6):1859-73.

doi: 10.1039/c6an00158k.

Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Yongkang Yue¹, Fangjun Huo², Caixia Yin¹, Jorge O Escobedo³, Robert M Strongin³

Affiliations

Affiliations

¹ Institute of Molecular Science, Shanxi University, Taiyuan 030006, China. yincx@sxu.edu.cn.
² Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China.
³ Department of Chemistry, Portland State University, Portland, OR 97201, USA. strongin@pdx.edu.

PMID: 26883493
PMCID: PMC4789306
DOI: 10.1039/c6an00158k

Review

Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid

Yongkang Yue et al. Analyst. 2016.

. 2016 Mar 21;141(6):1859-73.

doi: 10.1039/c6an00158k.

Authors

Yongkang Yue¹, Fangjun Huo², Caixia Yin¹, Jorge O Escobedo³, Robert M Strongin³

Affiliations

¹ Institute of Molecular Science, Shanxi University, Taiyuan 030006, China. yincx@sxu.edu.cn.
² Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China.
³ Department of Chemistry, Portland State University, Portland, OR 97201, USA. strongin@pdx.edu.

PMID: 26883493
PMCID: PMC4789306
DOI: 10.1039/c6an00158k

Abstract

Due to the biological and industrial importance of hypochlorous acid, the development of optical probes for HOCl has been an active research area. Hypochlorous acid and hypochlorite can oxidize electron-rich analytes with accompanying changes in molecular sensor spectroscopic profiles. Probes for such processes may monitor HOCl levels in the environment or in an organism and via bio-labeling or bioimaging techniques. This review summarizes recent developments in the area of chromogenic and fluorogenic chemosensors for HOCl.

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Figures

Fig. 1 — Fig. 1
The detection mechanism of probe 1 towards HOCl and structures of probe 2a, 2b, and 2c.

Fig. 2 — Fig. 2
The reaction of probe 3 and ClO⁻.

Fig. 3 — Fig. 3
The reaction of probe 4 and HOCl.

Fig. 4 — Fig. 4
The reaction of probe 5 and HOCl.

Fig. 5 — Fig. 5
The reaction of probe 6 and HOCl.

Fig. 6 — Fig. 6
The reaction of probe 7 and HOCl.

Fig. 7 — Fig. 7
The reaction of probe 8 and ClO⁻.

Fig. 8 — Fig. 8
The reaction of probes 9a and 9b with ClO⁻.

Fig. 9 — Fig. 9
The reaction of probe 10 and ClO⁻.

Fig. 10 — Fig. 10
The reaction of probe 11 and ClO⁻.

Fig. 11 — Fig. 11
The reaction of probe 12 and ClO⁻.

Fig. 12 — Fig. 12
The reaction of probe 13 with HOCl.

Fig. 13 — Fig. 13
The reaction of probe 14 and HOCl.

Fig. 14 — Fig. 14
The reaction of probe 15 and HOCl.

Fig. 15 — Fig. 15
The reaction of probe 16 and HOCl.

Fig. 16 — Fig. 16
The reaction of probe 17 and ClO⁻.

Fig. 17 — Fig. 17
The reaction of probe 18 and HOCl.

Fig. 18 — Fig. 18
The reaction of probe 19 and HOCl.

Fig. 19 — Fig. 19
The reaction of probe 20 and HOCl.

Fig. 20 — Fig. 20
The reaction of probe 21 and ClO⁻.

Fig. 21 — Fig. 21
The reaction of probe 22 and HOCl.

Fig. 22 — Fig. 22
The reaction of probe 23 and ClO⁻.

Fig. 23 — Fig. 23
The reaction of probe 24 and HOCl.

Fig. 24 — Fig. 24
Top: the reaction of probe 25 and HOCl. Bottom: proposed detection mechanism of HOCl.

Fig. 25 — Fig. 25
The reaction of probe 26 and HOCl.

Fig. 26 — Fig. 26
The reaction of probe 27 and ClO⁻.

Fig. 27 — Fig. 27
The reaction of probe 28 and HOCl.

Fig. 28 — Fig. 28
The reaction of probe 29 and HOCl.

Fig. 29 — Fig. 29
The reaction of probe 30 and HOCl.

Fig. 30 — Fig. 30
Structures of the two-photon probes and the proposed detection mechanism.

Fig. 31 — Fig. 31
Top: the reaction of probe 32 and ClO⁻. Bottom: proposed detection mechanism.

Fig. 32 — Fig. 32
Top: FRET-based ratiometric imaging of HOCl by probe 33. Bottom: proposed oxidation mechanism.

Fig. 33 — Fig. 33
Proposed detection mechanism of ClO⁻ detection using an AuNPs-dithiothreitol system.

Fig. 34 — Fig. 34
Top: reaction of 35 with HOCl. Bottom: (A, C) absorption spectra and (B, D) emission spectra of 35 with HOCl in different pH buffer solutions (A, B, pH = 7.4). Reprinted with permission from J. Am. Chem. Soc., 2013, 135, 13365–13370. Copyright 2013, American Chemical Society.

Fig. 35 — Fig. 35
The reaction of probe 36 and HOCl.

Fig. 36 — Fig. 36
The reaction of probe 37 and HOCl.

Fig. 37 — Fig. 37
The reaction of probe 38 and HOCl.

Fig. 38 — Fig. 38
The reaction of probe 39 and HOCl.

Fig. 39 — Fig. 39
Top: reaction of probe 40 and HOCl. Bottom: proposed detection mechanism of HOCl.

Fig. 40 — Fig. 40
The reaction of probe 41 and NaClO.

Fig. 41 — Fig. 41
The reaction of probe 42 and HOCl.

Fig. 42 — Fig. 42
The reaction of probe 43 and HOCl.

Fig. 43 — Fig. 43
The reaction of probe 44 and HOCl.

Fig. 44 — Fig. 44
The reaction of probe 45 and HOCl/ClO−.

Fig. 45 — Fig. 45
The reaction of probe 46 and ClO⁻.

Fig. 46 — Fig. 46
Top: reaction of probe 47 and HOCl. Bottom: (a) UV-vis responses of 47 to HOCl and the corresponding color changes. Reprinted with permission from Anal. Chem., 2014, 86, 671–677. Copyright 2014, American Chemical Society.

Fig. 47 — Fig. 47
Proposed detection mechanism of ClO⁻ by probe 48.

Fig. 48 — Fig. 48
Proposed detection mechanism of HOCl by probe 49.

Fig. 49 — Fig. 49
Proposed detection mechanism of HOCl by probe 50.

Fig. 50 — Fig. 50
Proposed detection mechanism of HOCl when using probe 51.

Fig. 51 — Fig. 51
Reaction of probe 52 and HOCl.

Scheme 1 — Scheme 1
The oxidation of p-methoxyphenol by HOCl.

Scheme 2 — Scheme 2
The specific oxidation reaction between oximes and HOCl.

Scheme 3 — Scheme 3
The specific chlorination reaction between thiols or amides and HOCl.

Scheme 4 — Scheme 4
The reaction of p-aminophenol analogues and HOCl.

Scheme 5 — Scheme 5
The oxidation reaction between thioethers, selenides and HOCl.

Scheme 6 — Scheme 6
HOCl-induced double bond cleavage.

Scheme 7 — Scheme 7
The specific oxidation reaction of cuprous to cupric with HOCl.

See this image and copyright information in PMC

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