Synthesis and metal ion-sensing properties of fluorescent PET chemosensors based on the 2-phenylimidazo[5,4-a]anthraquinone chromophore

Yoshida, Katsuhira; Mori, Takayoshi; Watanabe, Shigeru; Kawai, Hideki; Nagamura, Toshihiko

doi:10.1039/a900424f

Cited by 35 publications

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“…ureas, 35,64,65 thioureas, 44,[66][67][68] imidazoles/benzimidazoles, 21,45,[69][70][71][72][73][74][75] amides/diamides, [76][77][78] indolocarbazoles, 30,79,80 guanidinium derivatives, 81 azophenol, 31,82 naphthalimides, [83][84][85][86][87] pyrrole, 88,89 callixpyrrole [90][91][92][93] etc. The benzimidazole derivatives work via the deprotonation of N-H groups which results in either fluorescence quenching, 45,94 photoinduced electron transfer (PET) [95][96][97] or intramolecular charge transfer (ICT) processes. 21,75,98 The ICT process involves a 'push-pull' mechanism between a donor (D) and an acceptor (A) moiety and binding of the negatively charged analyte to the electron deficient acceptor (A) moieties modulates the charge transfer character of the D-A system.…”

Section: Introductionmentioning

confidence: 99%

Colorimetric detection of fluoride ions by anthraimidazoledione based sensors in the presence of Cu(ii) ions

2016

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Anthraquinone based anion receptors have gained importance due to their colorimetric response on sensing a specific anion and the possibility of tuning this property by varying the conjugated moiety (the donor) to the diamine. In this work, we have synthesized and characterized four anthraimidazoledione compounds having 2,5-dihydroxy benzene, 4-(bis(2-chloroethyl)amino)benzene, imidazole and 4-methylthiazole moieties respectively (1-4). All of them were probed for their potential as anion sensors to study the effect of changes in the hydrogen bond donor-acceptor. The p-hydroquinone bound anthraimidazoledione (1) and thioimidazole bound anthraimidazoledione (4) were able to detect both F(-) and CN(-) in the presence of other anions Cl(-), Br(-), I(-), H2PO4(-), OAc(-), NO3(-)and ClO4(-). Both 1 and 4 could not differentiate F(-) from CN(-) and provided a similar response to both. The 1H NMR studies of 1 and 4 with F(-) showed the formation of [HF2](-) at 16.3 ppm and the 19F NMR showed a sharp peak at -145 ppm in both cases. However, although there may be NMR evidence of [HF2](-) formation F(-) may not be detected colorimetrically if the CT band remains almost unchanged, as found for 3. The results emphasize that the change of a hetero atom in the donor moiety of an anthraimidazoledione may render a large difference in sensitivity. In the case of 4 selective detection of F(-) was possible in the presence of 0.5 equivalent of Cu2+ with the exhibition of a distinct green colour with a Δλ shift of ca. 50 nm in contrast to CN(-) which showed orange colouration with a Δλ shift of only 15 nm. In the presence of Cu2+ the F(-) detection limit was 0.038(5) ppm (below the WHO specified level) at a receptor concentration of 25 μM.

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Section: Introductionmentioning

confidence: 99%

Colorimetric detection of fluoride ions by anthraimidazoledione based sensors in the presence of Cu(ii) ions

2016

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“…[5–8] Important picosecond laser studies on fluorescent PET sensors/switches have demonstrated the transient existence of radical ion species,[9–11] and thus designers can proceed with confidence. As a result of their modular fluorophore-spacer-receptor construction, fluorescent PET systems are very amenable to modification in terms of the format, as well as in terms of the detailed functionalities.…”

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confidence: 99%

“…This also represents a new extension to modular switch systems based on photoinduced electron transfer (PET) towards the emulation of analogue electronic devices.Fluorescent photoinduced electron transfer (PET) sensors/ switches [1][2][3][4] are a well-established application of molecular devices, to the point of real-life deployment worldwide in blood electrolyte diagnostics. [5][6][7][8] Important picosecond laser studies on fluorescent PET sensors/switches have demonstrated the transient existence of radical ion species, [9][10][11] and thus designers can proceed with confidence. As a result of their modular fluorophore-spacer-receptor construction, fluorescent PET systems are very amenable to modification in terms of the format, as well as in terms of the detailed functionalities.…”

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confidence: 99%

Modification of Fluorescent Photoinduced Electron Transfer (PET) Sensors/Switches To Produce Molecular Photo‐Ionic Triode Action

Huxley¹,

Schroeder²,

Gunaratne³

et al. 2014

Angew Chem Int Ed

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“…[5][6][7][8] Important picosecond laser studies on fluorescent PET sensors/switches have demonstrated the transient existence of radical ion species, [9][10][11] and thus designers can proceed with confidence. As a result of their modular fluorophore-spacer-receptor construction, fluorescent PET systems are very amenable to modification in terms of the format, as well as in terms of the detailed functionalities.…”

mentioning

confidence: 99%

Modification of Fluorescent Photoinduced Electron Transfer (PET) Sensors/Switches To Produce Molecular Photo‐Ionic Triode Action

Huxley¹,

Schroeder²,

Gunaratne³

et al. 2014

Angewandte Chemie

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The fluorophore-spacer 1 -receptor 1 -spacer 2 -receptor 2 system (where receptor 2 alone is photoredox-inactive) shows ionically tunable proton-induced fluorescence off-on switching, which is reminiscent of thermionic triode behavior. This also represents a new extension to modular switch systems based on photoinduced electron transfer (PET) towards the emulation of analogue electronic devices.Fluorescent photoinduced electron transfer (PET) sensors/ switches [1][2][3][4] are a well-established application of molecular devices, to the point of real-life deployment worldwide in blood electrolyte diagnostics. [5][6][7][8] Important picosecond laser studies on fluorescent PET sensors/switches have demonstrated the transient existence of radical ion species, [9][10][11] and thus designers can proceed with confidence. As a result of their modular fluorophore-spacer-receptor construction, fluorescent PET systems are very amenable to modification in terms of the format, as well as in terms of the detailed functionalities. The latter approach has yielded many individual examples of sensors and switches based on fluorescence which target important analytes. [12][13][14][15] On the other hand, the former approach has the potential to set up new areas of endeavor and application, which is exploited here.The controllable quenching of molecular fluorescence [1,2] can be exploited to build switchable systems which emulate familiar electronic devices. Some of these molecular systems have unique applications which are inconvenient for their electronic counterparts, such as wireless operation in micrometric spaces. [16] The first molecular logic gate [17][18][19][20][21][22][23] 1 (an advanced molecular switch [24] ) was a fluorophore-spacer 1 -receptor 1 -spacer 2 -receptor 2 system, [25,26] where two photoinduced electron transfer (PET) [4, 27] channels arising from the two receptors were controlled by binding H + and Na + ions, respectively, and thus the fluorescence output corresponded to photo-ionic AND logic. Strong fluorescence emerges only when all PET processes are suppressed (Figure 1 a). [4] Related, but distinct, fluorophore-spacer 1 -receptor 1 -spacer 2 -receptor 2 systems, [28] where both receptors respond to H + ions, for example, 2, give rise to fluorescent off-on-off action, which can correspond to ternary logic behavior. [22] We now demonstrate aspects of molecular photo-ionic triode action for the first time by structurally mutating the fluorophore-spacer 1 -receptor 1 -spacer 2 -receptor 2 system 1 into a novel format exemplified by 3, where the convenient photoredox capability of receptor 2 is removed from 1 (Figure 1 b). Nearly 20 distinct formats of luminescent PET switching systems, each possessing its own defining features and applications, are known. [26] Fluorescence off-on switching is, therefore, controlled within 3 by selective ion binding of receptor 1 . This switching profile is influenced by the orthogonally selective ion binding of receptor 2 , which is forced into a secondary role...

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Synthesis and metal ion-sensing properties of fluorescent PET chemosensors based on the 2-phenylimidazo[5,4-a]anthraquinone chromophore

Cited by 35 publications

References 0 publications

Colorimetric detection of fluoride ions by anthraimidazoledione based sensors in the presence of Cu(ii) ions

Colorimetric detection of fluoride ions by anthraimidazoledione based sensors in the presence of Cu(ii) ions

Modification of Fluorescent Photoinduced Electron Transfer (PET) Sensors/Switches To Produce Molecular Photo‐Ionic Triode Action

Modification of Fluorescent Photoinduced Electron Transfer (PET) Sensors/Switches To Produce Molecular Photo‐Ionic Triode Action

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