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Review
. 2009 Jun;38(6):1647-62.
doi: 10.1039/b804436h. Epub 2009 Mar 30.

Modern reaction-based indicator systems

Dong-Gyu Cho  1 , Jonathan L Sessler
Affiliations
Review

Modern reaction-based indicator systems

Dong-Gyu Cho et al. Chem Soc Rev. 2009 Jun.

Abstract

Traditional analyte-specific synthetic receptors or sensors have been developed on the basis of supramolecular interactions (e.g., hydrogen bonding, electrostatics, weak coordinative bonds). Unfortunately, this approach is often subject to limitations. As a result, increasing attention within the chemical sensor community is turning to the use of analyte-specific molecular indicators, wherein substrate-triggered reactions are used to signal the presence of a given analyte. This tutorial review highlights recent reaction-based indicator systems that have been used to detect selected anions, cations, reactive oxygen species, and neutral substrates.

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Figures

Fig. 1
Fig. 1
Schematic illustration of conventional sensors and reaction-based sensors.
Scheme 1
Scheme 1
Proposed mechanism for the reaction-based detection of cyanide ion by indicator 1.
Scheme 2
Scheme 2
Proposed mechanism for the reaction-based detection of cyanide ion by indicator 3.
Scheme 3
Scheme 3
Proposed mechanism for the reaction-based detection of cyanide ion by indicator 5.
Scheme 4
Scheme 4
Proposed mechanism for the reaction-based detection of cyanide ion by indicator 10.
Scheme 5
Scheme 5
Proposed mechanism for the reaction-based detection of cyanide ion by indicator 11.
Scheme 6
Scheme 6
Proposed mechanism for the reaction-based detection of cyanide ion by indicator 13.
Scheme 7
Scheme 7
Proposed mechanism for the reaction-based detection of cyanide ion by indicator 15.
Scheme 8
Scheme 8
Proposed mechanism for the reaction-based detection of fluoride by indicator 17.
Scheme 9
Scheme 9
Proposed mechanism for the reaction-based detection of fluoride by indicator 20.
Scheme 10
Scheme 10
Synthesis and proposed mechanism of action for the fluoride indicator 22. Conditions: (a) MeOTf, CH2Cl2, 25 °C, 88%. (c) [Me3SIF2][S(NMe2)3], CH2Cl2, 25 °C, 64%.
Scheme 11
Scheme 11
Cyanide- and fluoride-sensing reactions of indicators 24 and 26.
Scheme 12
Scheme 12
Fluoride selective indicators whose mode of action involves deprotonation.
Scheme 13
Scheme 13
Proposed mechanism for the reaction-based detection of mercury by indicator 33.
Scheme 14
Scheme 14
Proposed mercury-sensing mechanism of 35.
Scheme 15
Scheme 15
Proposed mechanism for the reaction-based detection of mercury by indicator 37.
Scheme 16
Scheme 16
Mercury(II)-induced conversion of 39 to zwitterion 40 and the thiol-based regeneration of 39.
Scheme 17
Scheme 17
Proposed mechanism for the reaction-based detection of mercury by indicator 41.
Scheme 18
Scheme 18
Proposed mechanism for the reaction-based detection of mercury by indicator 43.
Scheme 19
Scheme 19
Proposed mechanism for the reaction-based detection of mercury by indicator 45.
Scheme 20
Scheme 20
Proposed mechanism for the reaction-based detection of mercury by indicator 47.
Scheme 21
Scheme 21
Proposed mechanism for the reaction-based detection of mercury by indicator 49.
Scheme 22
Scheme 22
Proposed copper(II)-based reactions considered relevant to an understanding of indicator 51.
Scheme 23
Scheme 23
Palladium-dependent reactions of 53.
Scheme 24
Scheme 24
Additional palladium-dependent reactions of 53.
Scheme 25
Scheme 25
Rudkevich’s phosgene-sensing strategy, which relies on the reaction between 56 and 57.
Scheme 26
Scheme 26
Hydrogen peroxide-sensing reaction of 59.
Scheme 27
Scheme 27
Hydrogen peroxide-sensing reaction of 61.
Scheme 28
Scheme 28
Hydrogen peroxide-induced transformation of indicator 63 into product 64 and the FRET pathway expected in the latter species.
Scheme 29
Scheme 29
(a) Reactions of TNT and DNT that have traditionally been used for sensing. (b) Reaction of RDX that has been used for the same purpose.
Scheme 30
Scheme 30
A reaction used to detect the presence of TNT.
Scheme 31
Scheme 31
Proposed lead-sensing mechanism of 72.
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References

    1. Arigaand K, Kunitake T. Supramolecular Chemistry: Fundamentals and Applications. Springer; Heidelberg: 2006.

    1. A considerable body of literature exists that deals with this topic. See, for instance: Sessler JL, Gale PA, Cho W-S. Anion Receptor Chemistry. The Royal Society of Chemistry; Cambridge, UK: 2006. Beer PD, Gale PA. Angew Chem, Int Ed. 2001;41:486–516.Valeur B, Leray I. Coord Chem Rev. 2000;205:3–40.

    1. Cyanohydrin reaction-based indicators differ from most other systems considered in this review in that they are for the most part based on reactions that are reversible.

    1. Mohr GJ. Chem–Eur J. 2004;10:1082–1090. - PubMed
    1. Kim YH, Hong JI. Chem Commun. 2002:512–513. - PubMed
    2. Anzenbacher P, Jr, Tyson DS, Jursíková K, Castellano FN. J Am Chem Soc. 2002;124:6232–6233. - PubMed

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