Synthesis and photoisomerization of mesogenic 4-alkoxystyrylpyridines

Turanova, O. A.; Gafiyatullin, L. G.; Гнездилов, О. И.; Туранов, А. Н.

doi:10.1134/s1070363211050173

Cited by 5 publications

(7 citation statements)

References 13 publications

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“…Further photoirradiation at 340 nm for 480 min resulted in a decrease in absorbance at around 300 nm and appearance of a peak at 247 nm (red line). These spectral shifts are due to cyclization and subsequent oxidation to a benzoquinoline derivative as shown in Scheme a . The cyclized product was detected by ESI-MS (see Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

p-Stilbazole Moieties As Artificial Base Pairs for Photo-Cross-Linking of DNA Duplex

et al. 2013

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In this study, we report a photo-cross-linking reaction between p-stilbazole moieties. p-Stilbazoles were introduced into base-paring positions of complementary DNA strands. The [2 + 2] photocycloaddition reaction occurred rapidly upon light irradiation at 340 nm. Consequently, duplex was cross-linked and highly stabilized after 3 min irradiation. The CD spectrum of the cross-linked duplex indicated that the B-form double-helical structure was not severely distorted. NMR analysis revealed only one conformation of the duplex prior to UV irradiation, whereas two diastereomers were detected after the photo-cross-linking reaction. Before UV irradiation, p-stilbazole can adopt two different stacking modes because of rotation around the single bond between the phenyl and vinyl groups; these conformations cannot be discriminated on the NMR time scale due to rapid interconversion. However, photo-cross-linking fixed the conformation and enabled discrimination both by NMR and HPLC. The artificial base pair of p-methylstilbazolium showed almost the same reactivity as p-stilbazole, indicating that positive charge does not affect the reactivity. When a natural nucleobase was present in the complementary strand opposite p-stilbazole, the duplex was significantly destabilized relative to the duplex with paired p-stilbazole moieties and no photoreaction occurred between p-stilbazole and the nucleobase. The p-stilbazole pair has potential as a "third base pair" for nanomaterials due to its high stability and superb orthogonality.

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Section: Resultsmentioning

confidence: 99%

p-Stilbazole Moieties As Artificial Base Pairs for Photo-Cross-Linking of DNA Duplex

et al. 2013

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“…STB and DPE purchased from Sigma-Aldrich (96%) and also deuterated acetone were used without prior purification. SP was synthesized according to the procedure (19)(20)(21).…”

Section: Methodsmentioning

confidence: 99%

“…dehydrogenated cycle. The photoisomerization of stilbene (27)(28)(29) and styrylpyridine (19,20) occurs according to the same scheme.…”

Section: Uv-vis Spectroscopymentioning

confidence: 99%

“…This multiplet consists of four lines of the spin system АА'XX' (30). NMR spectra of STB and SP are described in refs (19,20,31).…”

Section: Nmr Spectroscopymentioning

confidence: 99%

“…The process of photoisomerization of stilbene-like ligands in solutions depends on the irradiation wavelength and on the solvent (18). Previously, we studied the photoisomerization kinetics of 4-styrylpyridine and its 4-alkoxy derivatives at different irradiation wavelengths (k = 365 and 254 nm) and in various solvents (19,20). Although DPE is actively used in the synthesis of coordination compounds, its geometric isomerism has not yet been sufficiently studied.…”

Section: Introductionmentioning

confidence: 99%

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Photoisomerization of 1,2‐Di(4‐pyridyl)ethylene According to NMR and UV Spectroscopy Data and Density Functional Modeling

Shaidullina

Sharipova

Volkov

et al. 2023

Photochem & Photobiology

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Photoisomerization of 1,2‐di(4‐pyridyl)ethylene under UV irradiation was studied by NMR and UV spectroscopy in solutions of acetone, acetonitrile and chloroform. It has been established that in the studied solutions under irradiation, geometric photoisomerization occurs: the trans‐isomer transforms into the cis‐isomer and then cyclization occurs. DFT modeling of the listed processes, states and UV absorption spectra of the sample in an acetonitrile solution was performed.

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Synthesis of 1‐phenyl‐3‐(quinolin‐8‐ylamino)prop‐2‐en‐1‐one and analysis of its structure by X‐ray crystallography, NMR, UV‐Vis spectroscopy and DFT calculations

Volkov,

Sharipova,

Turanova

et al. 2024

ChemistrySelect

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Abstract1‐phenyl‐3‐(quinolin‐8‐ylamino)prop‐2‐en‐1‐one was obtained by a two‐step synthesis. From X‐ray crystallography, NMR and UV‐vis spectra it follows that in the crystalline state and in solutions, regardless of the polarity of the solvent, 1‐phenyl‐3‐(quinolin‐8‐ylamino)prop‐2‐en‐1‐one exists in the ketone form of the cis‐isomer. DFT calculations confirmed that the cis‐isomer is the most energetically favorable among all its isomers.

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Synthesis and photoisomerization of mesogenic 4-alkoxystyrylpyridines

Cited by 5 publications

References 13 publications

p-Stilbazole Moieties As Artificial Base Pairs for Photo-Cross-Linking of DNA Duplex

p-Stilbazole Moieties As Artificial Base Pairs for Photo-Cross-Linking of DNA Duplex

Photoisomerization of 1,2‐Di(4‐pyridyl)ethylene According to NMR and UV Spectroscopy Data and Density Functional Modeling

Synthesis of 1‐phenyl‐3‐(quinolin‐8‐ylamino)prop‐2‐en‐1‐one and analysis of its structure by X‐ray crystallography, NMR, UV‐Vis spectroscopy and DFT calculations

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