Effect of Interchromophoric Stacking Interactions on the Stability of the Sandwich-Type Complexes of 1-Hydroxy-9,10-anthraquinone-9-iminobenzo-15-crown-5 ether with Metal Cations

Timofey P. Martyanov,^a@ Evgeny N. Ushakov,^a,b@ and Lubov S. Klimenko^c

^aInstitute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russian Federation

^bPhotochemistry Center, Russian Academy of Sciences, 119421 Moscow, Russian Federation

^cYugra State University, 628012 Khanty-Mansiysk, Russian Federation

^@Corresponding author E-mail: martyanov.t@gmail.com; en-ushakov@mail.ru

DOI: 10.6060/mhc130746m

Macroheterocycles 2013 6(3) 240-244

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Tautomeric chromoionophore L binds strontium and barium cations to form sandwich-type complexes that surpass significantly the corresponding 1:1 complexes in the thermodynamic stability.

References

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1. Raymo F. M., Stoddart J. F. Chem. Rev. 1999, 99, 1643–1663.
http://dx.doi.org/10.1021/cr970081q

2. Ushakov E. N., Vedernikov A. I., Alfimov M. V., Gromov S. P. Photochem. Photobiol. Sci. 2011, 10, 15-18.
http://dx.doi.org/10.1039/c0pp00227e

3. Vedernikov A. I., Ushakov E. N., Efremova A. A., Kuz'mina L.G., Moiseeva A. A., Lobova N. A., Churakov A. V., Strelenko Yu.A., Alfimov M. V., Howard J. A.K., Gromov S. P. J. Org. Chem. 2011, 76, 6768-6779.
http://dx.doi.org/10.1021/jo201172w

4. Ushakov E.N., Alfimov M.V., Gromov S.P. Macroheterocycles 2010, 3, 189-200.

5. Pedersen C.J. J. Am. Chem. Soc. 1970, 92, 386-391.
http://dx.doi.org/10.1021/ja00705a605

6. Thanabal V., Krishnan V. J. Am. Chem. Soc. 1982, 104, 3643-3650.
http://dx.doi.org/10.1021/ja00377a016

7. Kobayashi N., Lever A.B.P. J. Am. Chem. Soc. 1987, 109, 7433-7441.
http://dx.doi.org/10.1021/ja00258a030

8. Dubonosov A.D., Minkin V.I., Bren V. A., Shepelenko E. N., Tsukanov A. V., Starikov A. G., Borodkin G. S. Tetrahedron 2008, 64, 3160-3167.
http://dx.doi.org/10.1016/j.tet.2008.01.096

9. Dubonosov A. D., Tsukanov A. V., Shepelenko E. N., Revinskii Yu.V., Bren V.A., Minkin V. I. Russ. J. Org. Chem. 2009, 45, 200-205.
http://dx.doi.org/10.1134/S1070428009020079

10. Hayvali Z., Yardimci D. Transition Met. Chem. 2008, 33, 421-429.
http://dx.doi.org/10.1007/s11243-008-9060-4

11. Chapoteau E., Czech B. P., Gebauer C. R., Kumar A., Leong K., Mytych D. T., Zazulak W., Desai D. H., Luboch E., Krzykawski J., Bartsch R. A. J. Org. Chem. 1991, 56, 2575-2579.
http://dx.doi.org/10.1021/jo00007a057

12. Hayvali Z., Hayvali M., Kiliç Z., Hökelek T., Weber E. J. Incl. Phen. Macrocycl. Chem. 2003, 45, 285-294.
http://dx.doi.org/10.1023/A:1024568309739

13. Martyanov T. P., Ushakov E. N., Savelyev V. A., Klimenko L. S. Russ. Chem. Bull. 2012, 61, 2282-2294.
http://dx.doi.org/10.1007/s11172-012-0323-z

14. Gritsan N. P., Klimenko L. S., Leonenko Z. V., Mainagashev I. Ya., Mamatyuk V. I., Vetchinov V. P. Tetrahedron 1995, 51, 3061-3076.
http://dx.doi.org/10.1016/0040-4020(95)00046-B

15. Mood A. M., Graybill F. A., Boes D. C. Introduction to the Theory of Statistics. New York: McGraw-Hill., 3rd ed., 1974, 540 p.

16. Ushakov E. N., Gromov S. P., Fedorova O. A., Pershina Yu.V., Alfimov M. V., Barigilletti F., Flamigni L., Balzani V. J. Phys. Chem. A 1999, 103, 11188-11193.
http://dx.doi.org/10.1021/jp9929420

17. Gromov S. P., Vedernikov A. I., Ushakov E. N., Kuz'mina L.G., Feofanov A. V., Avakyan V. G., Churakov A. V., Alaverdyan Yu.S., Malysheva E. V., Alfimov M. V., Howard J. A.K., Eliasson B., Edlund U. G. Helv. Chim. Acta 2002, 85, 60-81.
http://dx.doi.org/10.1002/1522-2675(200201)85:1<60::AID-HLCA60>3.0.CO;2-C

18. Takeda Y., Kumazawa T. Bull. Chem. Soc. Jpn. 1988, 61, 655-658.
http://dx.doi.org/10.1246/bcsj.61.655

19. Becke A. D. Phys. Rev. A 1988, 38, 3098-3100.
http://dx.doi.org/10.1103/PhysRevA.38.3098

20. Lee C., Yang W., Parr R.G. Phys. Rev. B 1988, 37, 785-789.
http://dx.doi.org/10.1103/PhysRevB.37.785

21. Weigend F., Ahlrichs R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
http://dx.doi.org/10.1039/b508541a

22. Grimme S., Antony J., Ehrlich S., Krieg H. J. Chem. Phys. 2010, 132, 154104-19.

23. Klimenko L. S., Kusov S. Z., Vlasov V. M., Tchabueva E. N., Boldyrev V. V. Mendeleev Commun. 2006, 16, 224-225.
http://dx.doi.org/10.1070/MC2006v016n04ABEH002294

24. Halgren T. A. J. Comp. Chem. 1999, 20, 720-729.

25. Neese F. WIREs Comput. Mol. Sci. 2012, 2, 73-78.
http://dx.doi.org/10.1002/wcms.81

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