ИСТИНА

A number of styryl dyes 1 and their corresponding bases were synthesized. It was found that dyes 1 can spontaneously form dimers 2 in both the solid state and in solution (MeCN,CH2Cl2). The dimers have a head-to-tail pseudocyclic structure. The dimerization stability constants for dyes 1 were estimated by 1H NMR titration in MeCN-d3 (logKd up to 8.0) [1, 2]. The complexation of styryl dyes and bases 1 with cucurbit[n]urils (CB[n], n = 7, 8) and β-, γ-cyclodextrins (CD) was studied by electron spectroscopy, NMR and X-ray [3, 4]. It was found that in aqueous solutions the addition of complementary cavitands (CB [7], β-CD) to compounds 1 lead to inclusion complexes of 1: 1 with a pseudorotaxane structure. For cavitands with a large cavity size (CB [8], γ-CD), the formation of complexes 2 of higher stoichiometry is also possible. [2+2] photocycloaddition reaction generate cyclobutane derivatives 3. For dyes the photocycloaddition quantum yield was varied between 0 and 0.38. The possibility of reaction passing depends on the nature of the compound 1 and the steric volume of its fragments. The structures of 1-3 were studied by X-ray diffraction and NMR spectroscopy. Dyes and bases 1 can be utilized in systems of optical registration and storage of information. References [1] Gromov S. P., Lobova N. A., Vedernikov A. I., Kuzґmina L. G., et.al., Russ. Chem. Bull., 2009, 58, 1211. [2] Gromov S. P., Vedernikov A. I., Lobova N. A., Kuz’mina L. G., et.al., J. Org. Chem., 2014, 79, 11416. [3] S.P. Gromov, A.I. Vedernikov, L.G. Kuz’mina, D.V. et.al., Eur. J. Org. Chem., 2010, 2587. [4] D.A. Ivanov, N.Kh. Petrov, A.A. Ivanov, M.V. Alfimov, A.I. Vedernikov, S.P. Gromov, Chem. Phys. Lett., 2014, 91, 610–611.