Dyes and Pigments, volume 172, pages 107825

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

Martyanov Timofey P ¹

Ushakov Evgeny N

Alfimov Michael V ²

Kuz'mina Lyudmila G. ³

Howard Judith A. K.

Vedernikov Artem I. ²

Gromov Sergey P

Sazonov Sergey K ²

Aleksandrova Nadezhda A ²

Lobova Natalia A ²

Ushakov E.N. ¹

Howard Judith A. ⁴

Fomina Marina V. ^{1, 5}

Hide authors affiliations Show authors affiliations: 5 affiliations

Photochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, Moscow, 119421, Russian Federation

Photochemistry Center

FSRC "Crystallography and photonics" of NRC «Kurchatov Institute»

Photochemistry Center of RAS, FSRC Crystallography and Photonics, Russian Academy of Sciences, Novatorov Str. 7A-1, Moscow, 119421, Russian Federation

Photochemistry Center

FSRC "Crystallography and photonics" of NRC «Kurchatov Institute»

N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences , Leninskiy prosp. 31, Moscow 119991, Russian Federation. |

⁴

‡Department of Chemistry, Durham University, South Road, Durham DH1 3LE, United Kingdom. |

⁵

Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russian Federation |

Publication type: Journal Article

Publication date: 2020-01-01

Elsevier

Journal: Dyes and Pigments

Quartile SCImago

Quartile WOS

Impact factor: 4.5

ISSN: 01437208, 18733743

DOI: 10.1016/j.dyepig.2019.107825

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General Chemical Engineering

Process Chemistry and Technology

Abstract

Abstract The study addresses the spectral and photochemical properties of N-(3-ammoniopropyl)-4-styrylpyridinium diperchlorate and its substituted analogs containing either electron-donating (OMe, SMe, NMe2) or electron-withdrawing (NO2, Cl) groups on the benzene ring. These styryl dyes in MeCN form pseudodimeric complexes with uncharged 18-crown-6-containing 4-styrylpyridine due to hydrogen bonding between the ammonium group and the crown ether oxygen atoms. The stability constants of the complexes were determined by spectrophotometric and 1H NMR titration methods. Owing to complexation, the dyes containing OMe or SMe groups and the dye with unsubstituted benzene ring undergo a stereospecific [2 + 2]-cross-photocycloaddition to the crown-containing styrylpyridine to give unsymmetrical cyclobutane derivatives as single rctt isomers. The structure of cyclobutanes was confirmed by X-ray diffraction analysis. The most probable conformations of the pseudodimeric complexes in MeCN were determined by density functional theory calculations. The cross-photocycloaddition quantum yields, measured upon selective excitation of the styryl dye, and other relevant data suggested that the barrier for this photoreaction increases with an increase in the reorganization energy of the singlet excited state of the dye.

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Dyes and Pigments	Dyes and Pigments, 1, 16.67% Dyes and Pigments 1 publication, 16.67%
Journal of Organic Chemistry	Journal of Organic Chemistry, 1, 16.67% Journal of Organic Chemistry 1 publication, 16.67%
Inorganica Chimica Acta	Inorganica Chimica Acta, 1, 16.67% Inorganica Chimica Acta 1 publication, 16.67%
ACS Omega	ACS Omega, 1, 16.67% ACS Omega 1 publication, 16.67%
Carbohydrate Polymers	Carbohydrate Polymers, 1, 16.67% Carbohydrate Polymers 1 publication, 16.67%
Chemical Communications	Chemical Communications, 1, 16.67% Chemical Communications 1 publication, 16.67%
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Elsevier	Elsevier, 3, 50% Elsevier 3 publications, 50%
American Chemical Society (ACS)	American Chemical Society (ACS), 2, 33.33% American Chemical Society (ACS) 2 publications, 33.33%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 1, 16.67% Royal Society of Chemistry (RSC) 1 publication, 16.67%
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Martyanov T. P. et al. Pseudodimeric complexes of 4-styrylpyridine derivatives: Structure–property relationships and a stereospecific [2+2]-cross-photocycloaddition in solution // Dyes and Pigments. 2020. Vol. 172. p. 107825.

GOST all authors (up to 50) Copy

Martyanov T. P., Vedernikov A. I., Ushakov E. N., Sazonov S. K., Aleksandrova N. A., Lobova N. A., Kuz'mina L. G., Howard J. A. K., Alfimov M. V., Gromov S. P., Ushakov E., Howard J. A., Fomina M. V. Pseudodimeric complexes of 4-styrylpyridine derivatives: Structure–property relationships and a stereospecific [2+2]-cross-photocycloaddition in solution // Dyes and Pigments. 2020. Vol. 172. p. 107825.

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RIS Copy

TY - JOUR

DO - 10.1016/j.dyepig.2019.107825

UR - https://doi.org/10.1016%2Fj.dyepig.2019.107825

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

T2 - Dyes and Pigments

AU - Martyanov, Timofey P

AU - Vedernikov, Artem I.

AU - Ushakov, Evgeny N

AU - Sazonov, Sergey K

AU - Aleksandrova, Nadezhda A

AU - Lobova, Natalia A

AU - Kuz'mina, Lyudmila G.

AU - Howard, Judith A. K.

AU - Alfimov, Michael V

AU - Gromov, Sergey P

AU - Ushakov, E.N.

AU - Howard, Judith A.

AU - Fomina, Marina V.

PY - 2020

DA - 2020/01/01 00:00:00

PB - Elsevier

SP - 107825

VL - 172

SN - 0143-7208

SN - 1873-3743

ER -

BibTex

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BibTex Copy

@article{2020_Martyanov,

author = {Timofey P Martyanov and Artem I. Vedernikov and Evgeny N Ushakov and Sergey K Sazonov and Nadezhda A Aleksandrova and Natalia A Lobova and Lyudmila G. Kuz'mina and Judith A. K. Howard and Michael V Alfimov and Sergey P Gromov and E.N. Ushakov and Judith A. Howard and Marina V. Fomina},

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

journal = {Dyes and Pigments},

year = {2020},

volume = {172},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016%2Fj.dyepig.2019.107825},

pages = {107825},

doi = {10.1016/j.dyepig.2019.107825}

}

Found error?

Publisher

Elsevier

Journal

Dyes and Pigments

Quartile SCImago

Quartile WOS

Impact factor

4.5

ISSN

01437208 (Print)
18733743 (Electronic)

Labs

Laboratory of Synthesis and Supramolecular Chemistry of Photoactive Compounds

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