Fluorescent Probes Containing Selenium as a Guest or Host

Wu, Di; Chen, Liyan; Kwon, Nahyun; Yoon, Juyoung

doi:10.1016/j.chempr.2016.10.005

Cited by 76 publications

(52 citation statements)

References 104 publications

(122 reference statements)

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“…Left:EPR spectrum of [3]C À (1:e xperiment, 2:s imulation), hyperfine coupling constants G,and g factor (experiment/DKH2-UB3LYP calculations with relativistically re-contracted DKH-def2-tzvp basisset for C, H, Na nd SARS-DKH-def2-tzvp for Te): a 14 N (1,3) = 5.85/5.08, g = 1.9952/1.9945. No hyperfine splitting with 1 Hn ucleiw as experimentally observed due to the line broadening.DFT: aH (4,7) = 2.62, aH (5,6) = 1.48. Right: EPR spectraof [ 2]C À (red and violet lines) and [3]C À (green and bluel ines) featuring shifto fg factor (1: experiment, 2:simulation).…”

Section: Chemical Reductionmentioning

confidence: 99%

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Radical Anions, Radical‐Anion Salts, and Anionic Complexes of 2,1,3‐Benzochalcogenadiazoles

Pushkarevsky

Chulanova

Shundrin

et al. 2018

Chemistry A European J

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With cyclic voltammetry (CV) and DFT calculations, it was found that electron acceptor ability of the 2,1,3-benzochalcogenadiazoles 1-3 (chalcogen: S, Se and Te, respectively) increases with the atomic number of chalcogen. This trend is nontrivial since it contradicts the electronegativity and atomic electron affinity of the chalcogens. In contrast to radical anions (RAs) [1]*- and [2]*-, RA [3]*- was not detected by EPR under the CV conditions. Chemical reduction of 1-3 was performed and new thermally-stable RA salts [K(THF)]+[2]*- (8) and [K(18-crown-6)]+[2]*- (9) were isolated in addition to known salt [K(THF)]+[1]*- (7). Upon contact with air, RAs [1]*- and [2]*- underwent fast decomposition in solution with the formation of anions [ECN]- isolated in the form of salts [K(18-crown-6)]+[ECN]- (10, E = S; 11, E = Se). In the case of 3, RA [3]*- was detected by EPR to be the first representative of tellurium-nitrogen π-heterocyclic RAs but not isolated. Instead, salt [K(18-crown-6)]+2[3-Te2]2- (12) featuring a new anionic complex with the coordinate bond Te-Te was obtained. Upon contact with air, salt 12 transformed into salt [K(18-crown-6)]+2[3-Te4-3]2- (13) revealing an anionic complex with two coordinate bonds Te-Te. The structures of 8-13 were confirmed by X-ray diffraction and the nature of the coordinate bonds Te-Te in [3-Te2]2- and [3-Te4-3]2- was studied with DFT calculations and QTAIM analysis.

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Section: Chemical Reductionmentioning

confidence: 99%

“…Solution(left; 1:e xperiment, 2:s imulation) and solid-state (right) EPR spectra of salt 9.H yperfine coupling constants G and g factor of[2]C À (experiment/UB3LYP/def2-tzvp): a 14 N (1,3) = 5.73/4.17, aH (4,7) = 2.36/2.96, aH(5,6) = 1.61/1.47, g = 2.0064/2.0068.…”

mentioning

confidence: 99%

Radical Anions, Radical‐Anion Salts, and Anionic Complexes of 2,1,3‐Benzochalcogenadiazoles

Pushkarevsky

Chulanova

Shundrin

et al. 2018

Chemistry A European J

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“…In this study, we designed a colorimetric system which can selectively sense thiophenol. A dinitrobenzene moiety has been proven to be an effective trigger group for the design of colorimetric probes to discriminate thiophenols from other aliphatic thiols by taking advantage of their different p K a values (6.5 and 8.5 for thiophenols and aliphatic thiols, respectively) . On the other hand, phenolphthalein is a typical pH indicator and it is well known for making color changes colorless to pink changes depending on basic conditions.…”

Section: Methodsmentioning

confidence: 99%

“…Ad initrobenzenem oiety has been proven to be an effective trigger group for the design of colorimetricp robes to discriminate thiophenols from other aliphatic thiols by taking advantage of their different pK a values (6.5 and 8.5 for thiophenols anda liphatic thiols, respectively). [4,[26][27][28][29][30] On the other hand, phenolphthalein is at ypical pH indicator andi ti sw ell knownf or making color changes colorless to pink changes depending on basic conditions. We prepared an ew phenolphthalein derivative 1 bearing ad initrophenylm oiety,w hich can react selectively with thiophenol at neutralp Ht op roduce phenolphthalein.…”

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Colorimetric Detection of Thiophenol Based on a Phenolphthalein Derivative and Its Application as a Molecular Logic Gate

et al. 2017

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A phenolphthalein‐based colorimetric probe bearing a dinitrobenzene group is reported as a thiophenol (PhSH)‐selective chemodosimeter. PhSH can react with chemodosimeter 1 to afford phenolphthalein. The addition of PhSH to the aqueous solution of 1 followed by a change in pH of the resulting solution to basic induces a selective color change from colorless to pink. Furthermore, using PhSH and base as inputs and color change of 1 by naked eye as an output, leads to the construction of an AND logic gate.

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“…[1][2][3][4][5][6] A vast library of chemosensors has been proposed so far, but only recently organoselenium and organotellurium compounds have been used for this purpose. 7,8,9 Heavy chalcogen-containing derivatives, and in particular those containing selenium, are of great interest because selenium compounds play an important role as enzymatic antioxidants participating in the conversion of hydrogen peroxides in water in biological systems. 10 In the particular case of seleniumcontaining chemosensors, the formation of highly stable selenoxides is often the event that triggers the optical recognition of analytes such as reactive oxygen species (ROS) superoxide, 11 hypochlorite 12 or reactive nitrogen species (RNS, for instance peroxynitrate).…”

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confidence: 99%

A new class of silica-supported chromo-fluorogenic chemosensors for anion recognition based on a selenourea scaffold

et al. 2017

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The development of optical chemosensors for neutral and charged species recognition has been one of the most active research field in Supramolecular Chemistry in the last 20 years. 1-6 A vast library of chemosensors has been proposed so far, but only recently organoselenium and organotellurium compounds have been used for this purpose. 7,8,9 Heavy chalcogen-containing derivatives, and in particular those containing selenium, are of great interest because selenium compounds play an important role as enzymatic antioxidants participating in the conversion of hydrogen peroxides in water in biological systems. 10 In the particular case of seleniumcontaining chemosensors, the formation of highly stable selenoxides is often the event that triggers the optical recognition of analytes such as reactive oxygen species (ROS) superoxide, 11 hypochlorite 12 or reactive nitrogen species (RNS, for instance peroxynitrate). 13 However, very few examples of selenium-containing optical chemosensors for "classic" anions such as fluoride 14 or carboxylates 15 have been described. In reported selenium-containing probes, the sensing mechanism of fluoride is based on a deprotonation event of an amino group, while carboxylate recognition depends on the formation of hydrogen bonds between the guest and pyrimidine and amide protons of the receptor. However, in both cases, selenium is contained in a selenodiazole moiety and do not actively participate to the sensing event.One of the most common strategy for the design of anion chemosensors is the use of hydrogen-bond donor groups such as urea or thiourea. In the case of thiourea-based chemosensors, due to the more acidic nature of the NHs protons (compared to those of the analogous urea derivatives), the recognition event is often caused by the deprotonation of the receptor that usually leads to a remarkable modification in the electronic properties of the system resulting in colour or emission changes. However, in this scenario, and, to the best of our knowledge, examples of selenourea-based anion sensors have never been reported in the literature to date despite selenoureas are interesting organoseleno compounds that show anticancer activity, antioxidant properties, enzyme inhibition, and DNA binding properties. [16][17][18][19][20] Taking these concepts into account and following our interest in anion recognition and sensing [21][22][23][24][25] we decided to explore the potential use of selenoureas as a new scaffold for the design of anion chemosensors.In particular, here, we describe the ability of the asymmetric 1-(4-methyl-2-oxo-2H-chromen-7-yl)-3-phenylselenourea (L) to act as a colorimetric and/or fluorescent sensor for S 2-and CNrecognition. L was obtained according to the reaction shown in Scheme 1.Scheme 1. Synthesis of 1-(4-methyl-2-oxo-2H-chromen-7-yl)-3-phenylselenourea (L).Phenylisoselenocyanate was synthesised following a literature procedure. 26 Reaction with 7-amino-4-methylcoumarin in DCM/EtOH (1:1, v/v) at 40°C for 3 hours under N2 atmosphere (Fig. 1) and CN -(see ESI...

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Fluorescent Probes Containing Selenium as a Guest or Host

Cited by 76 publications

References 104 publications

Radical Anions, Radical‐Anion Salts, and Anionic Complexes of 2,1,3‐Benzochalcogenadiazoles

Radical Anions, Radical‐Anion Salts, and Anionic Complexes of 2,1,3‐Benzochalcogenadiazoles

Colorimetric Detection of Thiophenol Based on a Phenolphthalein Derivative and Its Application as a Molecular Logic Gate

A new class of silica-supported chromo-fluorogenic chemosensors for anion recognition based on a selenourea scaffold

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