Metal Ions Drive Thermodynamics and Photochemistry of the Bis(styryl) Macrocyclic Tweezer

Tulyakova, Elena V.; Vermeersch, G.; Gulakova, E. N.; Федорова, О. А.; Fedorov, Yuri V.; Micheau, J. C.; Delbaere, Stéphanie

doi:10.1002/chem.200903226

Cited by 12 publications

(7 citation statements)

References 59 publications

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“…From another hand the substituent in the 5-position of the benzothiazole heterocycle sterically hinders the rotation of the alkylsulfo-anchoring group and thus plays the role of a controller with regard to its direction towards the crown ether. This finding is a resemblance to the results from reference [24] where the 5-methoxy-substituted benzothiazole styryl-crown ethers demonstrated higher quantum yields of trans- to- cis photoisomerization.…”

Section: Resultssupporting

confidence: 86%

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: Resultssupporting

confidence: 86%

Precious metal-free molecular machines for solar thermal energy storage

Kandinska¹,

Kitova²,

Videva³

et al. 2019

Beilstein J. Org. Chem.

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“…The small ionic diameter of the Mg II cation (1.56 Å) fits well with the size of the internal cavity of the benzo‐15‐crown‐5 ether unit and is expected to be inserted into the cavity thus surrounded by the oxygen atoms. The value of the binding constant (log K 11 =4.5±0.1) obtained from UV/Vis titration by Specfit calculations are in good agreement with our previously reported data for the benzo‐15‐crown‐5‐containing styryl dyes 5b…”

Section: Resultssupporting

confidence: 90%

“…UV/Vis Absorption: Measurements were performed according to the procedure described in ref. 5b. The binding constant and the stoichiometry were obtained from the titration curve by fitting these changes using the nonlinear regression analysis program SPECFIT32.…”

Section: Methodsmentioning

confidence: 99%

Photochromism and Metal Complexation of a Macrocyclic Styryl Naphthopyran

et al. 2011

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A macrocyclic benzo-15-crown-5 ether unit tethered to a photochromic naphthopyran by a styryl spacer (MEN) is shown to form a 1:1 complex with magnesium(II). The structure and dynamics of the specific host-metal interactions were investigated by PFG-NMR analysis. A combination of UV/Vis and variable temperature multi-dimensional (1)H NMR photokinetic analysis of the crown-containing styryl naphthopyran and its metal complex was used to probe the effect of metal complexation on the photochromism.

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“…Complexation of 1ae4a with Mg 2þ shortened the first fluorescence lifetime for all compounds and additionally led to the appearance of the second component for 3a and 4a. We assume that the second lifetime arises from the occasional formation of labile sandwich like structures of 2ae4a complexes with Mg 2þ due to the stack ing interactions between the heterocyclic fragments and the ex change of magnesium cations between the two crown ether units [18]. Complexation of the ligands with Ba 2þ resulted in the appearance of new very characteristic long living components in the timescale of 1000e3600 ps for compounds 2ae4a that were assigned to the formation of the tight syn sandwich dimers with the Ba 2þ cation ( Table 1).…”

Section: Time Resolved Fluorescence Spectroscopy Studiesmentioning

confidence: 99%

Regio- and stereoselective [2+2] photocycloaddition in Ba 2+ templated supramolecular dimers of styryl-derivatized aza-heterocycles

et al. 2017

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Metal Ions Drive Thermodynamics and Photochemistry of the Bis(styryl) Macrocyclic Tweezer

Abstract: In the Full Paper by S. Delbaere et al., the wrong journal was cited in reference [9c], the correct reference is included below. We apologize for this oversight.

Cited by 12 publications

References 59 publications

Precious metal-free molecular machines for solar thermal energy storage

Precious metal-free molecular machines for solar thermal energy storage

Photochromism and Metal Complexation of a Macrocyclic Styryl Naphthopyran

Regio- and stereoselective [2+2] photocycloaddition in Ba 2+ templated supramolecular dimers of styryl-derivatized aza-heterocycles

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