Thiacrown Ether Substituted Styryl Dyes:  Synthesis, Complex Formation and Multiphotochromic Properties

Федорова, О. А.; Fedorov, Yuri V.; Ведерников, А. И.; Gromov, S. P.; Yescheulova, Olga V.; Алфимов, М. В.; Woerner, M.; Bossmann, Stefan H.; Braun, André M.; Saltiel, Jack

doi:10.1021/jp014382m

Cited by 51 publications

(25 citation statements)

References 28 publications

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“…This result correlates with the degree of size match between the metal ion and the macrocyclic ring and is in agreement with literature data for relevant complexes [10,15,27,28], suggesting the formation of 1:2 sandwich or 1:2 linear complexes and 1:1 (in or above the macrocyclic ring) structure arrangements with different coordination numbers (Scheme 2). This observation reflects the known variation of the Ag(I) coordination number -with a preference between 2 and 6 -depending on the ligand used [24,33].…”

Section: Discussionsupporting

confidence: 91%

“…The benzothiaoxacrown compounds were prepared as described previously [25][26][27]. All the chemicals used were of analytical grade.…”

Section: Methodsmentioning

confidence: 99%

“…potentiostat/galvanostat with a 302A Static Mercury Drop Electrode (Princeton Applied Research) as described previously [27]. The potential scanning rate was 2 mV/s and the dropping time was 1 s. The supporting electrolyte was 0.01 M Et 4 NClO 4 .…”

Section: Stability Constant Determinationsmentioning

confidence: 99%

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Extraction Studies of Heavy Metal Ions Employing Benzothiaoxacrown Compounds

Tsend-Ayush

Wenzel

Gloe

et al. 2016

SERDJ

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Benzothiaoxacrown compounds with different numbers of sulfur and oxygen donor atoms (between 4 to 7 donors) dissolved in an organic diluent selectively extract the soft metal ions Ag(I) and Hg(II) from a mixture of Co(II), Ni(II), Cu(II), Zn(II), Ag(I) and Hg(II) present in an aqueous phase. Generally, the extraction efficiency depends on the specific structure of the benzothiaoxacrowns, on the organic diluent employed, as well as on the counter ion present in the aqueous phase. High extractions of Ag(I) and Hg(II) were achieved with all ligands from perchlorate and picrate aqueous media into nitrobenzene organic solutions. In the case of Cu(I) the extraction is significant lower; only ligand 5 with the O 2 S 4 donor atom set gives a moderate extractability. The composition of the extracted complexes depends on the crown ring size and ranges from 1:1 to 1:2 (M:L). Polarographic, UV-Vis and ESI mass spectrometric studies provide a further insight into the complex formation behavior.

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Section: Discussionsupporting

confidence: 91%

“…The benzothiaoxacrown compounds were prepared as described previously [25][26][27]. All the chemicals used were of analytical grade.…”

Section: Methodsmentioning

confidence: 99%

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Extraction Studies of Heavy Metal Ions Employing Benzothiaoxacrown Compounds

Tsend-Ayush

Wenzel

Gloe

et al. 2016

SERDJ

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“…The stability constants of the complexes 2a•Ag + , 2b•Ag + , and 2b•Pb 2+ in acetonitrile are several times larger than those of the corresponding complexes of styryl dyes 1a,b (logK = 5.6 (1b•Pb 2+ ), 14 4.1 (1a•Ag + ), and 4.8 (1b•Ag + ) 12 ). An analogous effect, viz., an increase in the thermodynamic stability of complexes after the re placement of the styryl chromophore with the butadienyl moiety has been observed earlier 9 for complexes of chro mogenic 15 crown 5 ethers with alkaline earth metal cat ions.…”

Section: Spectrophotometric Studymentioning

confidence: 83%

Crown-containing butadienyl dyes 8. Structures and complexation of chromogenic dithia-15(18)-crown-5(6) ethers

et al. 2006

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The structures of new butadienyl dyes of the benzothiazole series containing the dithia 15 crown 5 (2a) or dithia 18 crown 6 (2b) fragments were established by X ray diffraction. Com plexation of dyes 2a,b with Hg 2+ , Pb 2+ , Cd 2+ , Ag + , Zn 2+ , and alkaline earth cations in aqueous acetonitrile solutions was studied by spectrophotometry. At a high percentage of water in solutions (P w ≈ 50%), these dyes have a very low ability to bind Pb 2+ cations (logK < 2) and virtually do not bind Cd 2+ , Zn 2+ , and alkaline earth cations. At the same time, these dyes form stable 1 : 1 complexes with Hg 2+ and Ag + cations at all P w . The stability constants of complexes with the Ag + cation increase with increasing P w because the free energy of hydration of this cation is much lower than the free energy of solvation in acetonitrile. In the P w range from 0 to 75%, the stability constants of the complexes of dyes 2a,b with the Hg 2+ cation are larger than those of the corresponding complexes with the Ag + cation by more than four orders of magnitude.Crown ethers were first synthesized by Pedersen. 2 These compounds have found wide use in different fields of chemistry due to their ability to selectively bind alkali and alkaline earth cations. In particular, first selective reagents for the photometric determination of alkali cat ions were constructed based on crown ethers. 3,4 Most of the known chromogenic crown ethers (chromoiono phores) can be divided according to the mechanism of the metallochromic effect into two main groups. 5,6 One of these groups includes systems, in which the color changes occur due to bond dissociation in the chromophoric frag ment upon coordination of a metal cation to the macro cycle. Another group includes crown ethers containing a chromophoric fragment, which exists as a conjugated do nor-acceptor pair. In these systems, coordination of a metal cation to the macrocycle can cause a substantial electron density redistribution in the chromophoric frag ment and, as a consequence, the hypsochromic or batho chromic effect. The direction of color changes depends on which fragment of the chromophore (donor or accep tor) is bound to the polyether macrocycle. Crown con taining styryl and butadienyl dyes are examples of chromo ionophores, which show cation induced hypsochromic shifts. 7-9The properties of chromogenic crown ethers as selec tive reagents for the colorimetric determination of alkali and alkaline earth cations are rather well studied, whereas

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“…The crown-containing styryl dyes 87-90, which form molecular dimers in the presence of metal ions, were described in the cycle of papers [122][123][124][125][126][127][128]. During irradiation of solutions of the monomers stereospecific photocyclization takes place with the formation of only one or two derivatives of cyclobutane (of the 11 possible derivatives).…”

Section: Photoswitchable Chemosensorsmentioning

confidence: 99%

Organic chemosensors with crown-ether groups (review)

Цуканов

Дубоносов

Breń

et al. 2008

Chem Heterocycl Comp

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Recent advances in the chemistry of organic chemosensors containing crown-ether groups are reviewed.Organic chemosensors are molecules of abiotic nature capable of interacting selectively and irreversibly with a specific substrate (ion, molecule) with corresponding changes in one or more characteristics of the system. A series of reviews have described methods for the synthesis of chemosensors [1] and their use in the determination of metal cations [2-8], anions, and molecules [4, 9, 10]. Some of them treat the various types of fluorescent chemosensors [5][6][7][8] or photoswitching compounds [11][12][13][14] selectively. In this review, based exclusively on the results of recent years, sensors containing crown-ether groups are examined. Special attention is paid to the various mechanisms of action of crown-containing chemosensors, which are classified according to their electronic and photochemical characteristics.In the general case a chemosensor molecule consists of signal and receptor parts with a bridge between them although the latter may be absent. As a rule chemosensors can be subdivided into chromogenic, fluorescent, and photoswitchable.During the interaction of a chromogenic sensor with the substrate (in particular with a metal ion) a hypsochromic or bathochromic shift of the long-wave absorption band of the initial compound is observed. If the shift of the bands is significant and takes place in the visible part of the spectrum it leads to a visually discernable change in the color of the solution. Such signal systems are usually called colorimetric or "naked-eye" chemosensors.The action of fluorescent chemosensors is based both on change of the fluorescence intensity and on shift of the emission band of the initial compounds during the formation of a complex with the substrate.Photoswitchable chemosensors are capable of reversible "switching on-switching off" of their sensor characteristics under the influence of light.Among ionophore-receptors capable of combining with positively charged ions, it is possible to include chelating agents, podands, coronands (or crown ethers), cryptands, calixarenes, cyclodextrins, etc. [15].Crown ethers, discovered by Pedersen in 1962, occupy a special position among receptors and are widely used in the design of new chemosensors based on their unique ability to combine with the cations of alkali metals, their fairly high selectivity, and their accessibility. In addition to alkali metals, crown ethers are also effective complexing reagents for the cations of alkaline-earth metal, Pb 2+ , and Tl 2+ , and when nitrogen and sulfur atoms are inserted into their structure they become sensitive to Ag + , Hg 2+ , and Cd 2+ ions. The __________________________________________________________________________________________

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Thiacrown Ether Substituted Styryl Dyes: Synthesis, Complex Formation and Multiphotochromic Properties

Cited by 51 publications

References 28 publications

Extraction Studies of Heavy Metal Ions Employing Benzothiaoxacrown Compounds

Extraction Studies of Heavy Metal Ions Employing Benzothiaoxacrown Compounds

Crown-containing butadienyl dyes 8. Structures and complexation of chromogenic dithia-15(18)-crown-5(6) ethers

Organic chemosensors with crown-ether groups (review)

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