Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
7. References
Brown, G.H. (ed.) (1971) Photochromism, Wiley-Interscience, New York.
Durr, H., Bouas-Laurent, H. (eds.) (1990) Photochromism: Molecules and Systems, Elsevier, Amsterdam.
Crano, J.C., Guglielmetti, R. (eds.) (1999) Organic Photochromic and Thermochromic Compounds, Plenum Press, New York, v. 2.
McArdle, C.B. (ed.) (1992) Applied Photochromic Polymer Systems, Blackie, New York.
Alfimov, M.V., Fedorova, O.A., Gromov, S.P. (2003) Photoswitchable molecular receptors, Photochem. Photobiol. A,. 183–198.
Inoue, Y., Gokel, G. W. (eds.) (1990) Cation Binding by Macrocycles. Complexation of Cationic Speacies by Crown Ethers, Marcel Dekker Inc., New York and Basel.
a) Shinkai, S., Minami, T., Kusano, Y., Manabe, O. (1982) Photoresponsive crown ethers. 5. Light-driven ion transport by crown ethers with a photoresponsive anion cap, J. Am. Chem. Soc., 104, 1967–1972; b) Shinkai, S., Ishihara, M., Ueda, K., Monabe, O. (1985) Photoresponsive crown ether. Part 14. Photoregulated crown — metal complexation by competative intramolecular tail(ammonium)-biting, J. Chem. Soc. Perkin Trans. I, 511–518; c) Shinkai, S., Shigematsu, K., Sato, M., Manabe, O. (1982) Photoresponsive crown ether. Part 6. Ion transport mediated by photoinduced cis-trans interconversion of azobis(benzocrown ethers), J. Chem. Soc., Perkin Trans. 1, 2735–2739.
a) Durr, H., Thome, A., Kranz, C., Bossman, S. (1992) Supramolecular effects on photochromism-properties of crown ether-modified dihydroindolizines, J. Phys. Org. Chem., 111–149; b) Durr, H., Kranz, C., Kilburg, H. (1997) Supramolecular effects on photochromism-properties of crown ether-modified dihydroindolizines, Mol. Cryst. Liq. Cryst., 298, 89–96.
a) Guo, Z., Wang, G., Tang, Yi., Song, X. (1997) A crown ether bearing fulgides: the regulation of photochromism by supramolecular effect, Liebigs Ann. /Recueil., 941–942; b) Kawai, S. H. (1998) A crown ether bearing fulgides: the regulation of photochromism by supramolecular effect, Tetrahedron Lett., 39, 4445–4448.
Takeshita, M., Irie, M. (1998) Photoresponsive tweezers for alkali metal ions. Photochromic diarylethanes having two crown ether moieties, J. Org. Chem., 63, 6643–6649.
a) Bouas-Laurent, H., Castellan, A., Desvergne, J.-P., Lapouyade, R. (2001) Photodimerization of anthracenes in fluid solutions. Part 2. Mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage, R. Chem. Soc. Rev., 30, 248–263; b) Desvergne J.-P., Perez-Inestrosa E., Bouas-Laurent H., Jonusauskas G., Oberle J., Rullier C., in Valeur, B., Brochon J.-C. (eds.) (2001) New Trends in Fluorescence Spectroscopy. Application in Chemical and Life Sciences, Springer-Verlag, Berlin, Heidelberg, chapter 8; c) Desvergne, J.-P., Bouas-Laurent, H., Perez-Inestrosa, E., Marsua, P., Contrait, M. (1999) Photoinduced control of cation binding ability of non-conjugated bichromophoric receptors, Coord. Chem. Rev. 185–186, 357–371.
a) Inouye, M. (1996) Artificial-signaling receptors for biologically important chemical species, Coord. Chem. Rev. 148, 265–283; b) Inouye, M. (1998) «Purposive» molecular design for multifunctional artificial receptors, J. Incus. Phenom. Molecul. Recogn. Chem., 32, 223–233; c) Kimura, K., Sakamoto, H., Nakamura, M. (2003) Molecular design and application of photochromic crown compounds — How can we manipulate metal ions photochemically, Bull. Chem. Soc., Jpn., 76, 225–245; d) Tanaka, M., Kamada, K. (2003) Ion-responsive photochromic materials. Crowned spiropyranes, J. Synth. Org. Chem. Jpn., 61, 322–330.
Gromov, S.P., Alfimov, M.V. (1992) Supramolecular photochemistry of the crown ether styryl dyes, Russ. Chem. Bull., 46, 611–636.
a) Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Stanislavskii, O.B., Alfimov, M.V. (1991) Crown-containing styryl dyes. 2. Synthesis, photoinduced and dark complex formation of betainic chromogenic 15-crown-5-ether, Dokl. Akad. Nauk, 319, 1134–1139; b) Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Stanislavskii, O.B., Alfimov, M.V. (1991) Crown-containing styryl dyes. The size of helate macrocycle and complex formation of betainic photochromic 15-crown-5-ether, Dokl. Akad. Nauk, 321, 104–107; c) Gromov, S.P., Golosov, A.A., Fedorova, O.A., Levin, D.E., Alfimov, M.V. (1995) Nature of the heterocyclic moiety, complexation, and electronic absorption and fluorescence spectra of trans-and cis-isomers of photochromic 15-crown-5-ethers, Russ. Chem. Bull., 4, 124–130.
Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Baskin, I.I., Lindeman, A.V., Malysheva, E.V., Balashova, T.A., Arsen'ev, A., Alfimov, M.V. (1998) Crown ether styryl dyes. 24. Synthesis of multiphotochromic 15-crown-5 ethers with rigid spacers, their anion-“capped” complexes, and stereospecific [2+2]-autophotocycloaddition, Russ. Chem. Bull., 47, 97–105.
a) Ushakov, E.N., Gromov, S.P., Fedorova, O.A., Alfimov, M.V. (1997) Crown-containing styryl dyes. 19. Complexation and cation-induced aggregation of chromogenic aza-15-crown-5-ethers, Russ. Chem. Bull., 46, 463–471; b) Gromov, S.P., Ushakov, E.N., Fedorova, O.A., Soldatenkova, V.A., Alfimov, M.V. (1997) Crown-containing styryl dyes. 22. Synthesis and complexation of photochromic aza-15-crown-5-ethers, Russ. Chem. Bull., 46, 1143–1147.
Alfimov, M.V., Fedorov, Yu.V., Fedorova, O.A., Gromov, S.P., Hester, R.E., Lednev, I.K., Moore, J.N., Oleshko, V.P., Vedernikov, A.I. (1996) Synthesis and spectroscopic studies of novel photochromic benzodithiacrown ethers and their complexes, J. Chem. Soc., Perkin Trans. 2, 1441–1447.
Alfimov, M.V., Gromov, S.P., Fedorov, Yu.V., Fedorova, O.A., Vedernikov, A.I. (1997) Crown-containing styryl dyes. 23. Synthesis and complexation of cis-isomers of photochromic dithia-15(18)-crown-5(6)-ethers, Russ. Chem. Bull., 46, 2099–2106.
Alfimov, M.V., Vedernikov, A.I., Gromov, S.P., Fedorov, Yu.V., Fedorova, O.A., Churakov, A.V., Kuz'mina, L.G., Howard, J.A.K., Bossmann, S., Braun, A., Woerner, M., Sears, D.F., Saltiel, J. (1999) Synthesis, structure and ion selective complexation of trans and cis isomers of photochromic dithia-18-crown-6 ethers, J. Am. Chem. Soc., 121, 4992–5000; b) Stanislavskii, O.B., Ushakov, E.N., Gromov, S.P., Fedorova, O.A., Alfimov, M.V. (1996) Crown-containing styryl dyes. 14. The influence of N-substitute length on the complex formation of betainic chromogenic 15-crown-5-ether with alkaline earth metal cations, Russ. Chem. Bull., 45, 564–572.
Fedorova, O.A., Fedorov, Y.V., Vedernikov, A.I., Yescheulova, O.V., Gromov, S.P., Alfimov, M. V., Kuz'mina, L.G., Churakov, A.V., Howard, J.A.K., Zaitsev, S.Yu., Sergeeva, T.I., Möbius, D. (2002) Supramolecular assemblies of photochromic benzodithia-18-crown-6 ethers in crystals, solutions, and monolayers, New J. Chem., 26, 543–553.
Barzykin, A.V., Fox, M.A., Ushakov, E.N., Stanislavsky, O.B., Gromov, S.P., Fedorova, O.A., Alfimov, M.V. (1992) Dependence of metal ion complexation and intermolecular aggregation on photoinduced geometric isomerism in a crown ether styryl dye, J. Am. Chem. Soc., 114, 6381–6385.
Alfimov, M.V., Gromov, S.P., Stanislavskii, O.B., Ushakov, E.N., Fedorova, O.A. (1993) Crowncontaining styryl dyes. 8. Cation-dependent concerted [2+2]-autophotocycloaddition of photochromic 15-crown-5 ether betaines, Russ. Chem. Bull., 42, 1385–1389.
Gromov, S.P., Ushakov, E.N., Fedorova, O.A., Buevich, A.V., Alfimov, M.V. (1996) Crown-containing styryl dyes. 18. Synthesis, anion-“capped” complexes and ion-selective stereospecific [2+2]-autophotocycloaddition of photochromic 18-crown-6 ether, Russ. Chem. Bull., 45, 654–661.
Ushakov, E.N., Gromov, S.P., Buevich, A., Baskin, I.I., Fedorova, O.A., Vedernikov, A.I., Alfimov, M.V., Eliasson, B., Edlund, U. (1999) Crown-containing styryl dyes: cation-induced self-assembly of multiphotochromic 15-crown-5 ethers into photoswitchable molecular devices, J. Chem. Soc., Perkin Trans. 2, 601–607.
Fedorova, O.A., Fedorov, Y.V., Vedernikov, A. I., Gromov, S. P., Yescheulova, O.V., Alfimov, M.V., Woerner, M., Bossmann, S., Braun, A., Saltiel, J. (2002) Thiacrown Ether Substituted Styryl Dyes: Synthesis, Complex Formation and Multiphotochromic Properties, J. Phys. Chem. A, 106, 6213–6222.
Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Buevich, A.V., Alfimov, M.V. (1995) Crown-containing styryl dyes. 15. Synthesis and two pathways of the regio-and stereospecific cation-dependent [2+2]-autophotocycloaddition of chromogenic 15-crown-5 ether betaines of quinoline series, Russ. Chem. Bull., 4, 2131–2136.
Gromov, S.P., Ushakov, E.N., Fedorova, O.A., Baskin, I.I., Buevich, A.V., Andryukhina, E.N., Alfimov, M.V., Johnels, D., Edlund, U.G., Whitsel, J.K., Fox, M.A. (2003) Novel photoswitcable receptors: synthesis and cation-induced assembly into dimeric complexes leading to stereospecific [2+2]-photocycloaddition of styryl dyes containing a 15-crown-5 ether unit, J. Org. Chem., 68, 6115–6125.
Gromov, S.P., Fedorova, O.A., Ushakov, E.N., Buevich, A.V., Baskin, I.I., Pershina, Y.V., Eliasson, B., Edlund, U., Alfimov, M.V. (1999) Photoswitchable molecular pincers: synthesis, self-assembly into sandwich complexes and ion-selective intramolecular [2+2]-photocycloaddition of an unsaturated bis-15-crown-5 ether, J. Chem. Soc., Perkin Trans. 2, 1323–1329.
Ushakov, E.N., Gromov, S.P., Fedorova, O.A., Pershina, Y.V., Alfimov, M.V., Barigelletti, F., Flamigni, L., Balzani, V. (1999) Sandwich-Type Complexes of Alkaline-Earth Metal Cations with a Bisstyryl Dye Containing Two Crown Ether Units, J. Phys. Chem. A, 103, 11188–11193.
Fedorov, Y.V., Fedorova O.A., Gromov S.P., Bobrovsky M.B., Andrukhina E.N., Alfimov M.V. (2002) Simulation of optical responce to complex formation of crown-containing 2-styrylbenzothiazoles with alkaline-earth metals, Russ. Chem. Bull., 51, 789–795.
Fedorov, Yu.V., Fedorova, O.A., Andryukhina, E.N., Gromov, S.P., Alfimov, M.V., Kuzmina, L.G., Churakov, A.V., Howard, J.A.K., Aaron, J.-J. (2003) Ditopic complex formation of the crown-containing 2-styrylbenzothiazole, New J. Chem., 280–288.
Fedorova, O.A., Fedorov, Y.V., Andryukhina, E.N., Gromov, S.P., Alfimov, M.V. (2003) Cation-dependent photochromic properties of the novel ditopic receptors, Pure&Applied Chem., 1077–1084.
Fedorov, Yu., Fedorova, O., Schepel, N., Gromov, S., Alfimov, M., J. Saltiel (2004) Synthesis and multitopic complex formation of the photochromic bis-crown ether based on benzobis(thiazole), J. Phys. Org. Chem., in press.
Fedorova, O.A., Gromov, S.P., Pershina, Y.V., Sergeev, S.S., Strokach, Y.P., Barachevsky, V.A., Alfimov, M.V., Pèpe, G., Samat, A., Guglielmetti, R. (2000) Novel azacrown ether-containing spiro[indoline-2,3′-naphthoxazines]: design, synthesis and cation-dependent photochromism, J. Chem. Soc., Perkin Trans. 2, 563–571.
Fedorova, O.A., Gromov, S.P., Strokach, Yu.P., Pershina, Yu.V., Sergeev, S.A., Barachevsky, V.A., Pepe, G., Samat, A., Guglielmetti, R., Alfimov, M.V. (1999) Crown-containing spironaphthoxazines and spiropyrans. 1. Synthesis and anion-“capped” complexes of photochromic aza-15-crown-5 ethers with flexible spacers, Russ. Chem. Bull., 48, 1950–1959.
Fedorova, O.A., Strokach, Y.P., Gromov, S.P., Koshkin, A.V., Valova, T.M., Alfimov, M.V., Feofanov, A.V., Alaverdian, I.S., Lokshin, V.A., Samat, A., Guglielmetti, R., Girling, R.B., Moore, J.N., Hester, R.E. (2002) Effect of metal cations on the photochromic properties of spironaphthoxazines conjugated with aza-15(18)-crown-5(6) ethers, New J. Chem., 26, 1137–1145.
Fedorova, O.A., Koshkin, A.V., Gromov, S.P., Avakyn, V.G., Nazarov, V.B., Brichkin, S.B., Vershinnikova, T.G., Nikolaeva, T.M., Chernih, L.A., Alfimov, M.V. (2002) Crown-containing spironaphthoxazines and spiropyrans. 3. Synthesis and investigation of the open merocyanine form of the crown-containing spirobenzothiazolylnaphthoxazine, Russ. Chem. Bull., 51, 1441–1450.
Ushakov, E.N., Nazarov, V.B., Fedorova, O.A., Gromov, S.P., Chebun'kova, A.V., Alfimov, M.V., Barigelletti, Fr. (2003) Photocontrol of Ca2+ complexation with an azacrown-containing chromene, J. Phys. Org. Chem., 16, 306–309.
Fedorova, O.A., Maurel, Fr., Ushakov, E.N., Nazarov, V.B., Gromov, S.P., Chebun`kova, A.V., Feofanov, A.V., Alaverdian, I.S., Alfimov, M.V., Barigelletti, Fr. (2003) Synthesis, photochromic behaviour and light-controlled complexation of 3,3-diphenyl-3H-benzo[f]chromenes containing a dimethylamino group or an aza-15-crown-5 ether unit, New J. Chem., 27, 1155–1167.
Lokshin, V., Samat, A., Chebun'kova, A.V., Fedorova, O.A., Gromov, S.P., Strokach, Yu. P., Valova, T.M., Alfimov, M.V. (2004) Investigation of the Azacrown-Ether Substituted Naphtopyranes, Mol. Cryst. Liq. Cryst., in press.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2005 Springer
About this chapter
Cite this chapter
Fedorova, O.A., Ushakov, E.N., Fedorov, Y.V., Strokach, Y.P., Gromov, S.P. (2005). Macrocyclic Systems with Photoswitchable Functions. In: Gloe, K. (eds) Macrocyclic Chemistry. Springer, Dordrecht. https://doi.org/10.1007/1-4020-3687-6_15
Download citation
DOI: https://doi.org/10.1007/1-4020-3687-6_15
Publisher Name: Springer, Dordrecht
Print ISBN: 978-1-4020-3364-3
Online ISBN: 978-1-4020-3687-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)