Synthesis, photochemical and luminescent properties of (E)-2-(2-hydroxyarylethylene)-3-phenylquinazolin-4(3H)-ones / Ovchinnikova I.G., Kim G.A., Matochkina E.G., Kodess M.I., Barykin N.V., Eĺtsov O.S., Nosova E.V., Rusinov G.L., Charushin V.N. // Russian Chemical Bulletin. - 2014. - V. 63, l. 11. - P. 2467-2477.

ISSN:

10665285

Type:

Article

Abstract:

Photoinduced transformations of 2-styrylquinazolinones in solutions were studied using absorption and NMR spectroscopy methods. A possibility of control of the photochemical isomerization rate of quinazolinone 2-(hydroxyaryl)ethenyl derivatives by changing the pH of the medium was demonstrated. The bases and the solvent nature also affect the luminescence intensity of solutions of these compounds in the wavelength range of 550 - 650 nm. The differences in the steric organization of the ortho-hydroxystyryldiazinone system in crystals and in solutions related to the turn of the aryl group were found. Their influence on the competing processes of luminescence and photochemical transformation of the ethylene fragment were shown. The fact of reversible photo/thermal E-Z-isomerization was established for (E)-2-(2-hydroxystyryl)-3-phenylquinazolin-4(3H)-one. © 2014 Springer Science+Business Media New York.

Author keywords:

(E)-2-styrylquinazolin-4(3H)-ones; luminescence; ortho-hydroxystyrylquinazolinones; photoswitching; reversible photo/thermal isomerization

Index keywords:

нет данных

DOI:

10.1007/s11172-014-0764-7

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-84937682300&doi=10.1007%2fs11172-014-0764-7&partnerID=40&md5=4ef8540ed2228220750b638d56b10099

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-84937682300&doi=10.1007%2fs11172-014-0764-7&partnerID=40&md5=4ef8540ed2228220750b638d56b10099
Affiliations	I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 ul. S. Kovalevskoi, Ekaterinburg, Russian Federation; Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 ul. Mira, Ekaterinburg, Russian Federation
Author Keywords	(E)-2-styrylquinazolin-4(3H)-ones; luminescence; ortho-hydroxystyrylquinazolinones; photoswitching; reversible photo/thermal isomerization
References	Krasovitskii, B.N., Bolotin, B.M., (1984) Organicheskiye Lyuminofory [Organic Luminophores], p. 336; Irie, M., (2000) Chem. Rev., 100, p. 1685. , 1:CAS:528:DC%2BD3cXisFGitLc%3D; Gromov, S.P., Alfimov, M.V., (1997) Russ. Chem. Bull. (Engl. Transl.), 46, p. 638; Lipunova, G.N., Nosova, E.V., Trashakhova, T.V., Charushin, V.N., (2011) Russ. Chem. Rev., 80, p. 1115. , 1:CAS:528:DC%2BC38Xislenur8%3D; Lower, S.K., El-Sayed, M.A., (1966) Chem. Rev., 66, p. 199. , 1:CAS:528:DyaF28XovVeqtg%3D%3D; Dabiri, M., Baghbanzadeh, M., Delbari, A.S., (2008) J. Comb. Chem., 10, p. 700. , 1:CAS:528:DC%2BD1cXpt1yns78%3D; Bakalova, S.M., Santos, A.G., Timcheva, I., Kaneti, J., Filipova, I.L., Dobrikov, G.M., Dimitrov, V.D., (2004) J. Mol. Struct., 710, p. 229. , 1:CAS:528:DC%2BD2cXhtVClsLvI; Mashraqui, S.H., Ghorpade, S.S., Tripathi, S., Britto, S., (2012) Tetrahedron Lett., 53, p. 765. , 1:CAS:528:DC%2BC38XpsV2ksA%3D%3D; Trashakhova, T.V., Nosova, E.V., Valova, M.S., Slepukhin, P.A., Lipunova, G.N., Charushin, V.N., (2011) Russ. J. Org. Chem. (Engl. Transl.), 47, p. 753. , 1:CAS:528:DC%2BC3MXntlWqtL4%3D; Nosova, E.V., Stupina, T.V., Lipunova, G.N., Valova, M.S., Slepukhin, P.A., Charushin, V.N., (2012) Int. J. Org. Chem., 2, p. 56. , 1:CAS:528:DC%2BC38XhsVSls77J; Parker, C.A., Photoluminescence of Solutions, with Applications to Photochemistry and Analytical Chemistry (1968) Elsevier, Amsterdam, p. 208; Walker, G.N., (1955) J. Am. Chem. Soc., 77, p. 6698. , 1:CAS:528:DyaG28XkvVOktw%3D%3D; Nosova, E.V., Stupina, T.V., Lipunova, G.N., Charushin, V.N., (2013) Butlerovskiye Soobshch. [Butlerov Commun.], 33, p. 61; Lukyanova, E.L., (1980) Izmeriteĺsrednei Moshchnosti i Energii Lazernogo Izlucheniya IMO-2N [IMO-2N Meter of Average Power and Laser Irradiation Energy], , Volgograd (in Russian); CrysAlis Pro, Vers., , 171.33.66, Oxford Diffraction Ltd; Sheldrick, G.M., (2008) Acta Crystallogr., Sect. A, 64, p. 112. , 1:CAS:528:DC%2BD2sXhsVGhurzO; Tulyakova, E.V., Fedorova, O.A., Fedorov U. Y, V., Anisimov, A.V., (2008) J. Photochem. Photobiol. A: Chemistry, 200, p. 90. , 1:CAS:528:DC%2BD1cXhtF2msLbM; Carey, F.A., Sundberg, R.J., (2007) Adv. Org. Chem., Part A, 12, p. 1073; Marvell, E.N., Gosink, G.C.T.A., Zimmer, G., (1966) J. Am. Chem. Soc., 88, p. 619. , 1:CAS:528:DyaF28XosVOhsQ%3D%3D; Rodriguez-Otero, J., (1999) J. Org. Chem., 64, p. 6842. , 1:CAS:528:DyaK1MXltFKms7o%3D; Kurdyukova, I.V., Ishchenko, A.A., Derevyanko, N.A., Mysyk, D.D., (2013) Chem. Heterocycl. Compd., 49, p. 281. , 1:CAS:528:DC%2BC3sXptVWnsrs%3D; Oliveira, M.M., Salvador, M.A., Delbaere, S., Berthet, J., Vermeersch, G., Micheau, J.C., Coelho, P.J., Carvalho, L.M., (2008) J. Photochem. Photobiol. A: Chemistry, 198, p. 242. , 1:CAS:528:DC%2BD1cXntFGkt7k%3D
Correspondence Address	Ovchinnikova, I.G.; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 ul. S. Kovalevskoi, Russian Federation
Publisher	Springer New York LLC
CODEN	RCBUE
Language of Original Document	English
Abbreviated Source Title	Russ. Chem. Bull.
Source	Scopus