Molecular design, photoisomerization and complexation of crown ether styryl dyes

Алфимов, М. В.; Gromov, S. P.; Lednev, Igor K.

doi:10.1016/0009-2614(91)80242-p

Cited by 45 publications

(46 citation statements)

References 7 publications

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“…Thus, the invention of new materials possessing at least parts of these requirements provides the base for further improvements and brings the scientists nearer to the identification of the “perfect” MOST system. In this connection we identified crown ether-containing styryl dyes [14–15] as promising substances due to their ability to undergo trans- to- cis photoisomerization ( E / Z ) with very high quantum yields. In addition, their structures predispose to an easy functionalization and low cost synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…Another advantage of these dyes is the very low molar absorptivity [16–17] of the higher energy cis isomer, which is a prerequisite for its photostability. The cis isomers of styryl dyes linked to crown ethers have been identified to form complexes with alkaline-earth metal cations with higher stability constant than the respective trans isomer forms [14–15 18]. Lednev et al proposed as an explanation of the difference in the determined stability constants values for the complexes with cis/trans isomers the formation of an additional intramolecular coordination bond between the “crowned” cation and the alkylsulfonate anchoring group which is only possible for the cis form [19].…”

Section: Introductionmentioning

confidence: 99%

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Precious metal-free molecular machines for solar thermal energy storage

Kandinska¹,

Kitova²,

Videva³

et al. 2019

Beilstein J. Org. Chem.

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Four benzothiazolium crown ether-containing styryl dyes were prepared through an optimized synthetic procedure. Two of the dyes (4b and 4d) having substituents in the 5-position of the benzothiazole ring are newly synthesized compounds. They demonstrated a higher degree of trans–cis photoisomerization and a longer life time of the higher energy forms in comparison with the known analogs. The chemical structures of all dyes in the series were characterized by NMR, UV–vis, IR spectroscopy and elemental analysis. The steady-state photophysical properties of the dyes were elucidated. The stability constants of metal complexes were determined and are in good agreement with the literature data for reference dyes. The temporal evolution of trans-to-cis isomerization was observed in a real-time regime. The dyes demonstrated a low intrinsic fluorescence of their Ba2+ complexes and high yield of E/Z photoisomerization with lifetimes of the higher energy form longer than 500 seconds. Density functional theory (DFT) calculations at the B3LYP/6-31+G(d,p) level were performed in order to predict the enthalpies (H) of the cis and trans isomers and the storage energies (ΔH) for the systems studied.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Precious metal-free molecular machines for solar thermal energy storage

Kandinska¹,

Kitova²,

Videva³

et al. 2019

Beilstein J. Org. Chem.

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show abstract

“…This has focussed much research interest on the understanding of the mechanisms governing the spectroscopic behaviour of such systems [5][6][7][8][9][10][11][12][13]. Hydroxytriazenes and its derivatives are one of the best classes of fluorescent sensor molecules that can be used successfully in these areas.…”

Section: Introductionmentioning

confidence: 99%

Absorption and fluorescence spectroscopy of 3-hydroxy-3-phenyl-1-o-carboxyphenyltriazene and its copper (II), nickel (II) and zinc (II) complexes: a novel fluorescence sensor

Ressalan

Iyer

2005

Journal of Luminescence

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“…4) enabling the complete molecular photoswitch from the trans to the cis isomer and back with high quantum yields (ϕ ≈ 0.5). 59 Yet another interesting property of this dye is that its cis isomer can bind metal ions 500 times more stronger than the trans isomer. As a result, the complexation, which is not photosensitive by itself, can be controlled by light.…”

Section: Trans-cis Photoisomerizationmentioning

confidence: 99%

Molecular meccano for light-sensitive and light-emitting nanosized systems based on unsaturated and macrocyclic compounds

Gromov

2008

Russ Chem Bull

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The review presents the results of the development of an universal approach to the molecular design of light sensitive and light emitting nanosized systems with desired properties based on unsaturated and macrocyclic compounds. Within the same class of compounds, various nanosized systems were constructed using a limited number of structural fragments. These nanosized systems are susceptible to all main types of photoprocesses, such as fluorescence, photodissociation, photo isomerization, photocycloaddition, photoelectrocyclization, excimer formation, charge transfer com plex formation, the formation of the twisted intramolecular charge transfer state (TICT state), and the electron transfer. The use of photostructural transformations for controlling the complexation and mechanical movements in molecular devices and machines is discussed. The prospects of application of the new strategy are exemplified by the design of the previously unknown types of molecular switches, materials for optical chemosensors, optical data recording and storage media, photo switchable molecular devices, and photocontrolled molecular machines.

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Molecular design, photoisomerization and complexation of crown ether styryl dyes

Cited by 45 publications

References 7 publications

Precious metal-free molecular machines for solar thermal energy storage

Precious metal-free molecular machines for solar thermal energy storage

Absorption and fluorescence spectroscopy of 3-hydroxy-3-phenyl-1-o-carboxyphenyltriazene and its copper (II), nickel (II) and zinc (II) complexes: a novel fluorescence sensor

Molecular meccano for light-sensitive and light-emitting nanosized systems based on unsaturated and macrocyclic compounds

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