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

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Abstract

1-(3-Ammoniopropyl)-4-[(E)-2-(3,4-dichlorophenyl)vinyl]pyridinium diperchlorate was synthesized and its crystal structure was studied by X-ray diffraction. The photochemical properties of this compound and its complexation with a 18-crown-6-containing derivative of 4-styrylpyridine were studied by electronic spectroscopy. These compounds form a supramolecular complex (logK = 3.89 in MeCN at an ionic strength of 0.01 mol L–1), in which the styryl chromophores are arranged one above another due to stacking interactions. The complexation activates the cross [2+2] photocycloaddition of styrylpyridine derivatives. A procedure is proposed for the global analysis of spectrophotometric data, which takes into account the effect of the ionic strength of the solution on the observed equilibrium reaction.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    E. N. Ushakov

  2. Photochemistry Center, Russian Academy of Sciences, 7A-1 ul. Novatorov, 119421, Moscow, Russian Federation

    E. N. Ushakov, A. I. Vedernikov, S. K. Sazonov, M. V. Alfimov & S. P. Gromov

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

    L. G. Kuz´mina

  4. Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK

    J. A. K. Howard

Authors
  1. E. N. Ushakov
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  2. A. I. Vedernikov
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  4. L. G. Kuz´mina
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  5. M. V. Alfimov
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Correspondence to E. N. Ushakov or S. P. Gromov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0562—0572, March, 2015.

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Ushakov, E.N., Vedernikov, A.I., Sazonov, S.K. et al. Synthesis and photochemical study of a supramolecular pseudodimeric complex of 4-styrylpyridinium derivatives. Russ Chem Bull 64, 562–572 (2015). https://doi.org/10.1007/s11172-015-0901-y

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  • DOI: https://doi.org/10.1007/s11172-015-0901-y

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