Synthesis, Optical Characteristics and Complex Formation of Molecular Receptors Based on 1,8-Naphthalimide Derivatives in Solution and in Composition of Hybrid Tin Dioxide Nanoparticles

Antonina N. Arkhipova,^a Pavel A. Panchenko,^а,b Nikolai E. Schepel,^а Yuri V. Fedorov,^a Marina N. Rumyantseva,^с Artem V. Marikutsa,^c Alexander M. Gaskov,^с and Olga A. Fedorova^а,b,c@

^aA.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119991 Moscow, Russia

^bD.I. Mendeleev University of Chemisal Technology of Russia, 125047 Moscow, Russia

^cM.V. Lomonosov Moscow State University, Chemistry Department, 119992 Moscow, Russia

^@Corresponding author E-mail: fedorova@ineos.ac.ru

DOI: 10.6060/mhc161175f

Macroheterocycles 2017 10(1) 84-93

In the present work the synthesis of N-alkyl- and N-phenyl-1,8-naphthalimides containing dithiacrown ether, carboxyl group or both of these substituents has been developed. Molecular receptor 4-methoxy-N-benzodithiacrown-1,8-naphthalimide was synthesized from anhydride of 4-nitro-1,8-naphthalene dicarboxylic acid by acylation of crown-containing aniline and the replacement of nitro group onto methoxy one. Carboxylic derivatives of 1,8-naphthalimide with or without thiacrown ether moiety were prepared and the method of their covalent attachment to the SnO₂ surface has been proposed. Molecular receptor 4-methoxy-N-benzodithiacrown-1,8-naphthalimide demonstrates selectivity towards Hg²⁺ and Pb²⁺ cations in acetonintrile solution and towards Hg²⁺ in aqueous media. Due to its structure this receptor shows low fluorescence intensity in the free state and substantial increase of fluorescence in the presence of Hg²⁺ and Pb²⁺ is observed. This phenomenon is explained by the fact that an efficient photoinduced electron transfer takes place between fluorophore and receptor parts of the molecule in the absence of metal ions, resulting in fluorescence quenching. Electron transfer process is blocked in the presence of metal ions because the lone pair of electrons originally involved in the electron transfer process is engaged in metal ion binding. As a result the fluorescence enhancement is observed upon complexation with metal ions. 1,8-Naphthalimide derivatives in the composition of hybrid SnO₂ sol demonstrate optical characteristics similar to those of molecular fluorophores. However, the binding of metal ions by hybrid nanoreceptor was not observed. It should be due to effective interaction of crown-containing molecule with SnO₂ surface.

References:

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1. Le T.P., Rogers J.E., Kelly L.A. J. Phys. Chem. A 2000, 104, 6778-6785.
https://doi.org/10.1021/jp000855y

2. Cho D.W., Fujitsuka M., Sugimoto A., Yoon U.C., Mariano P.S., Majima T. J. Phys. Chem. B 2006, 110, 11062-11068.
https://doi.org/10.1021/jp057557r

3. May B., Poteau X., Yuan D., Brown R.G. Dyes Pigm. 1999, 42, 79-84.
https://doi.org/10.1016/S0143-7208(99)00011-X

4. a) Riu J., Maroto A., Rius F.X. Talanta 2006, 69, 288-301;
https://doi.org/10.1016/j.talanta.2005.09.045
b) Zhang X. Electrochemical Sensors, Biosensors and their Biomedical Applications Amsterdam, The Netherlands: Elsevier Inc. 2008;
c) Holder E., Tessler N., Rogach A.L. J. Mater. Chem. 2008, 18, 1064-1078.
https://doi.org/10.1039/b712176h

5. Krasovitsky B.M., Zubanova T.P., Vinetskaya Y.М. Chem. Heterocyclic Comp. 1982, 9, 1248-1250.
https://doi.org/10.1007/BF00513443

6. Gruzinskii V.V., Kukhto A.V., Shakkakh G.K. J. Appl. Spectrosc. 1998, 65, 463- 465.
https://doi.org/10.1007/BF02675471

7. Siegers C., Olàh B., Würfel U., Hohl-ebinger J., Hinsch A., Haag R. Solar Energ. Mater. Solar Cells 2009, 93, 552-563.
https://doi.org/10.1016/j.solmat.2008.11.038

8. Lin H.-H., Chan Y.-C., Chen J.-W., Chang C.-C. J. Mater. Chem. 2011, 21, 3170-3177.
https://doi.org/10.1039/c0jm02942d

9. Magalhães J.L., Pereira R.V., Triboni E.R., Filho P.B., Gehlen M.H., Nart F.C. Photochem. Photobiol. A 2006, 183, 165-170.
https://doi.org/10.1016/j.jphotochem.2006.03.012

10. Li Z., Yang Q., Qian X. Bioorg. Med. Chem. 2005, 13, 4864-4870.
https://doi.org/10.1016/j.bmc.2005.05.006

11. Batzill M., Diebold U. Prog. Surf. Sci. 2005, 79, 47-154.
https://doi.org/10.1016/j.progsurf.2005.09.002

12. Alfimov M. V., Gromov S. P., Fedorov Yu. V., Fedorova O. A., Vedernikov A. I.,Churakov A. V., Kuzmina L. G., Howard J. A. K., Bossmann S., Braun A., Woerner M., Sears D. F., Saltiel J. J. Am. Chem. Soc. 1999, 121, 4992-5000.
https://doi.org/10.1021/ja990370r

13. Panchenko P.A., Fedorov Y.V., Fedorova O.A., Izmailov B.A., Vasnev V.A., Istratov V.V., Makeeva E.A., Rumyantseva M.N., Gaskov A.M. Mendeleev Commun. 2011, 21, 12-14.
https://doi.org/10.1016/j.mencom.2011.01.005

14. Nardis S., Monti D., Di Natale C., D'Amico A., Siciliano P., Forleo A., Epifani M., Taurino A., Rella R., Paolesse R. Sens. Actuators B. 2004, 103, 339–343.
https://doi.org/10.1016/j.snb.2004.04.063

15. Callone E., Carturan G., Ischia M., Epifani M., Forleo A., Siciliano P., Paolesse R. Inorg. Chim. Acta. 2008, 361, 79–85.
https://doi.org/10.1016/j.ica.2007.06.030

16. Descalzo A.B., Martinez-Manez R., Radeglia R., Rurack K., Soto J. J. Am. Chem. Soc. 2003, 125, 3418-3419.
https://doi.org/10.1021/ja0290779

17. Okazaki M., Suhara Y., Uemura S., Fujiyama M., Oda K., Tanaka T., Taniguchi S., Watanabe Y. J. Soc. Organ. Synth. Chem., Jpn, 1956, 14, 455-459.

18. Okazaki M., Suhara Y., Oda K. J. Soc. Organ. Synth. Chem., Jpn, 1956, 14, 504-508.

19. Reynolds G.A., Drexhage K.H. Optics Commun. 1975, 13, 222-225.
https://doi.org/10.1016/0030-4018(75)90085-1

20. Lisitsyn V.N. Chemistry and Technology of Intermediates. Moscow: Khimiya, 1987. 368 p. (in Russ.)

21. Cao H., Chang V., Hernandez R., Heagy M.D. J. Org. Chem. 2005, 70, 4929-4934.
https://doi.org/10.1021/jo050157f

22. Silverstein Р., Bassler G., Morril Т. Spectrometric identification of organic compounds. New York: Wiley, 1977, 183 p.

23. Panchenko P.A., Fedorov Yu.V., Perevalov V.P., Jonusauskas G., Fedorova O.A. J. Phys. Chem. A 2010, 114, 4118-4122.
https://doi.org/10.1021/jp9103728

24. Panchenko P.А., Fedorov Y.V., Fedorova О.А., Perevalov V.P., Jonuskauskas G. Russ. Chem. Bull. 2009, 6, 1199-1206.
http://dx.doi.org/10.1007/s11172-009-0160-x

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Synthesis, Optical Characteristics and Complex Formation of Molecular Receptors Based on 1,8-Naphthalimide Derivatives in Solution and in Composition of Hybrid Tin Dioxide Nanoparticles

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