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2 article(s) from Gulevskaya, Anna V

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

Semyon V. Tsybulin,
Ekaterina A. Filatova,
Alexander F. Pozharskii,
Valery A. Ozeryanskii and
Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

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Figure 1: Proton sponge-based 1,4-diaryl-1,3-butadiynes synthesized previously and in this study.

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Figure 2: Target oligomers as push–pull and cross-conjugated π-systems.

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Scheme 1: Synthetic strategy for target oligomers 5.

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Scheme 2: Synthesis of 7-(arylethynyl)-2-ethynyl-DMAN 6.

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Scheme 3: Synthesis of 1,4-diaryl-1,3-butadiynes 5 and their salts 11.

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Figure 3: Molecular structures of compounds 5b (top), 5d (middle), and 5e (bottom).

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Figure 4: Views on the molecular backbone of compounds 5b (top), 5d (middle), and 5e (bottom) along the napht...

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Scheme 4: Transformation of butadiyne 5c into benzo[g]indole 12.

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Figure 5: Molecular structure of compound 11c: frontal (top; BF₄⁻ omitted) and side views (bottom; hydrogen a...

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Figure 6: Calculation of the qr parameter.

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Figure 7: Two π-conjugation ways in oligomers 5.

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Figure 8: UV–vis spectra of oligomers 5 (blue line), monomers 6 (red line), and butadiyne 1 (green line).

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Figure 9: UV–vis spectra of salts 11 (left), 1·2HBF₄ and 6b·HBF₄ (right) in acetonitrile.

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Figure 10: π-Conjugation pathway in salts 11b and 6b·HBF₄.

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Figure 11: Cyclic voltammograms of oligomers 5.

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Scheme 5: Possible ways of one- and two-electron oxidation of oligomers 5.

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Published 15 May 2023

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Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

Daria I. Tonkoglazova,
Anna V. Gulevskaya,
Konstantin A. Chistyakov and
Olga I. Askalepova

Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

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Scheme 1: Overview of the synthetic methods for the carbazole-based heterohelicenes. i) Pd₂dba₃, xantphos, K₃...

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Scheme 2: Synthetic strategy for the carbazole-based [6]helicenes fused with an azine ring.

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Scheme 3: Sonogashira coupling of compound 4b with phenylacetylene. i) Pd(PPh₃)₂Cl₂, CuI, iPr₂NH, DMSO, 80 °C...

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Figure 1: Molecular structure of carbazole-based [6]helicenes 10a (a), 10b (b) and 10c (c) (X-ray data).

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Figure 2: Crystal packing of carbazole-based [6]helicenes 10a (a, b), 10b (c,d) and 10c (e). Hydrogen atoms a...

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Published 04 Jan 2021

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