Synthesis and photochemical study of a supramolecular pseudodimeric complex of 4-styrylpyridinium derivatives

Ushakov, Evgeny N.; Ведерников, А. И.; Sazonov, S. K.; ́mina, L. G. Kuz; Алфимов, М. В.; Howard, Judith A. K.; Gromov, S. P.

doi:10.1007/s11172-015-0901-y

Cited by 6 publications

(11 citation statements)

References 35 publications

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“…This assumption was confirmed by preparative photolysis (see Experimental Section, Figure , and Figures S20–S26). The quantum yield of cross-PCA reaction Φ PCA was determined by a specific procedure described previously and used to determine Φ PCA for complex ( E )- 3· ( E )- 2b (Figures S5–S8). The results of measurements indicated that long-term irradiation of complex ( E )- 1· ( E )- 2b at λ = 405 nm was accompanied by consumption of both dye 2b and stilbene 1 (Figure S6).…”

Section: Resultsmentioning

confidence: 99%

“…The treatment of photoirradiation-dependent spectra was carried out using global analysis methods, as described previously. 11 The φ E−Z and φ Z−E values were determined to within ±20%.…”

Section: ■ Experimental Sectionmentioning

confidence: 95%

“…The dye consumption in the cross-PCA reaction was determined on the basis of spectrophotochemical data using the specific procedure reported previously. 11 The cross-PCA quantum yield obtained in this way is an effective value, since the complexed dye 2b is able to undergo the reversible E−Z photoisomerization.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The amount of the E isomer in the photostationary mixture was estimated from the fluorescence spectrum taking into account the fact that the Z isomer almost does not fluoresce. The treatment of photoirradiation-dependent spectra was carried out using global analysis methods, as described previously . The φ E–Z and φ Z–E values were determined to within ±20%.…”

Section: Experimental Sectionmentioning

confidence: 99%

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Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition

et al. 2021

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A new efficient method was proposed for the synthesis of (18-crown-6)stilbene; the structure of the product was confirmed by X-ray diffraction analysis. In MeCN, this compound forms pseudodimeric complexes with N-(2-ammonioethyl)-4-styrylpyridinium and N-(3-ammoniopropyl)-4-styrylpyridinium diperchlorates via hydrogen bonding between the ammonium group and the crown ether oxygen atoms. The ammonioethyl derivative was synthesized for the first time. The stability constants and spectral characteristics of the complexes were measured by spectrophotometric and fluorescence titration. Photoirradiation of the pseudodimeric complex of (18-crown-6)stilbene with the ammoniopropyl dye resulted in the stereospecific [2 + 2] cross-photocycloaddition reaction. The replacement of the stilbene moiety in the crown compound by a styrylpyridine moiety led to a 5-fold increase in the quantum yield of the photoprocess. The most probable cause for this effect is the presence of photoinduced electron transfer in (18-crown-6)stilbene complexes. This assumption is confirmed by fluorescence lifetime spectroscopy and density functional theory calculations.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 95%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

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Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition

et al. 2021

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“…The spectroscopic data were treated using global analysis methods, as described previously. 45 The photoisomerization quantum yields are measured to within ±20%.…”

Section: Methodsmentioning

confidence: 91%

Highly Stable Supramolecular Donor–Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure–Property Relationships

et al. 2020

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The physicochemical properties of highly stable supramolecular donor–acceptor (D–A) complexes of a bis(18-crown-6)azobenzene (weak π-donor) with a series of bis(ammonioalkyl) derivatives of viologen-like molecules (π-acceptors) in acetonitrile were studied using cyclic voltammetry, UV–vis absorption spectroscopy, 1 H NMR spectroscopy, and density functional theory (DFT) calculations. The crystalline structures of the bis(crown)azobenzene and its complex with a bis(ammoniopropyl) derivative of 2,7-diazapyrene were determined by X-ray diffraction analysis. In solution, all of the supramolecular D–A complexes studied have a pseudocyclic structure owing to ditopic coordination of the ammonium groups of the acceptor to the crown ether moieties of the donor. These complexes show somewhat lower stability as compared with the previously studied complexes of the related derivative of stilbene (strong π-donor), which is explained by the relatively weak intermolecular charge-transfer (CT) interactions. Time-dependent DFT calculations predict that the low-energy CT transition in the D–A complex of the bis(crown)azobenzene with a bis(ammoniopropyl) derivative of 4,4′-bipyridine lies between the local ππ* and n π* transitions of the azobenzene. The absorption band associated with the CT transition is indiscernible in the spectrum since it is overlapped with broad and more intense ππ* and n π* bands. It was found that the E → Z photoisomerization quantum yield of the bis(crown)azobenzene decreases by almost an order of magnitude upon the complexation with the 4,4′-bipyridine derivative. This effect was tentatively attributed to the intermolecular electron transfer that occurs in the 1 ππ* excited state of the azobenzene and competes with the 1 ππ* → 1 n π* internal conversion.

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Pseudodimeric complexes of 4-styrylpyridine derivatives: Structure–property relationships and a stereospecific [2+2]-cross-photocycloaddition in solution

et al. 2020

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Synthesis and photochemical study of a supramolecular pseudodimeric complex of 4-styrylpyridinium derivatives

Cited by 6 publications

References 35 publications

Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition

Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition

Highly Stable Supramolecular Donor–Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure–Property Relationships

Pseudodimeric complexes of 4-styrylpyridine derivatives: Structure–property relationships and a stereospecific [2+2]-cross-photocycloaddition in solution

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