Synthesis, NMR and X-Ray Diffraction Analysis of Boron Complexes Derived from Hydroxychalcones
Keywords:
Boron complexes, hydroxychalcones, diphenylboroni cacidAbstract
Abstract. The synthesis of a series of “push-pull” boron complexes obtained by reaction of hydroxychalcones with borontrifluoride etherate and diphenylboronic acid is described. These derivatives have potential application in non-linear optics, since they present a conjugated π system, a boron atom which can act as acceptor and a donor substituent at the para position.
Resumen. El presente trabajo describe la síntesis de una serie de complejos de boro “push-pull” preparados por reacción de hidroxichalconas con trifluoroboro eterato y ácido difenilborónico. Estos complejos podrían tener buenas propiedades de óptica no lineal, ya que presentan un sistema π, un átomo de boro que puede actuar como el grupo aceptor y el sustituyente en la posición para que actúa como el grupo donador.
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References
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3. Dalton, L. R.; Harper, A. W.; Ghosn, R.; Steier, W. H.; Ziari, M.; Fetterman, H.; Shi, Y.; Mustacich, R. V.; Jen, K. Y.; Shea, K. J. Chem Mater. 1995, 7, 1060-1081, Benning R. G., J. Mater. Chem. 1995, 5, 365-378; Verbiest T.; Houbrechts, S.; Kauranen M.; Clays, K.; Persoons A. J. Mater. Chem. 1997, 7, 2175-2189.
4. Lorimer, S. D.; Perry, N. B. Planta Med. 1994, 60, 386- 387.
5. Li, R.; Kenyon, G. L.; Cohen F.E.; Chen, X.; Gong, B.; Domínguez, J. N.; Davidson, E.; Kurzban, G.; Miller, R.E.; Nuzum, E. O.; Rosenthal, P. J.; McKerrow, J. H. J. Med. Chem.
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6. Makita, H.; Tanaka, T.; Fujitsuka, H.; Tatematsu, N.; Satoh, K.; Hara, A.; Mori, H. Cancer Res. 1996, 56, 4904-4909.
7. Lin, C. N.; Hsieh, H. K.; Ko, H. H.; Hsu, M. F.; Lin, H. C.; Chang, Y. L.; Chung, M. I.; Kang, J. J.; Wang, J. P.; Teng C. M. Drug Develop. Res. 2001, 53, 9-14.
8. Wang, P.; Wu, S. J. J. Lumin. 1994, 62, 33-39; Zhang, G.; Kinoshita, T.; Sasaki, K.; Goto, Y.; Nakayama, M. J. Cryst. Growth. 1990, 100, 411-416; Twieg, R. J.; Jain K. In: Nonlinear Optical Properties of Organic Molecules and Polymeric Materials. D. J. Williams Ed. ACS Symposium series 233. American Chemical Society. Washington, D. C. 1983; Tao, X. T.; Watanabe, T;. Kono, K.; Deguchi, T.; Nakayama, M.; Miyata, S. Chem. Mater. 1996, 8, 1326-1332.
9. Jiang, Y. B.; Wang, X. J.; Lin, L. J. Phys. Chem. 1994, 98, 12367-12372.
10. Palaniandavar, M.; Natarajan, C. Aust. J. Chem. 1980, 33, 737-745.
11. Biradar, N.S.; Patil, B.R.; Kulkarni, V.H. Inorg. Chim. Acta. 1976, 20, 183-185.
12. Rudzinski, W.E.; Aminabhavi, T.M.; Biradar, N.S.; Patil, C.S. Inorg. Chim. Acta. 1983, 70, 175-178
13. Singh, H.; Rathi, U.K. J. Indian Chem. Soc. 1979, 56, 1028-1030.
14. Birdar, N. S.; Patel, B.R.; Kulkarni, V.H. Inorg. Chim. Acta. 1975, 15, 33-38.
15. Debattista, N. B.; Pappano, N. B. Talanta 1997, 44, 1967-1971.
16. Montaña, M. P.; Pappano, N. B.;. Debattista, N. B Talanta 1998, 47, 729-733.
17. Raghava Naidu, R. Talanta 1975, 22, 614-616.
18. Hawthorne, M. F.; Lee M. W. J. Neurooncol. 2003, 62, 33-45. 19. Suginome, M.; Uehlin, L.; Yamamoto, A.; Murakami, M. Org Lett. 2004, 6, 1167-1169
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21. Yuang, Z. Taylor, N. J.; Marder, T. B.; Williams, I. D.; Kurtz, S. K.; Cheng, L. T.; J. Chem. Soc. Chem. Commun., 1990, 1489-1492.
22. Bosio, L.; Lequan, R. M.; Lequan, M.; Vandevyver, M. New. J. Chem., 1995, 19, 141-143.
23. Lambert, C.; Stadler, S.; Bourhill G.; Brauchle, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 644-646.
24. Lesley M. J. G.; Woogward A.; Taylor, N. J.; Marder, T. B.;Cazenobe, I.; Ledoux, I.; Zyss, J.; Thornton, A.; Bruce, D. W.; Kakkar, A. K. Chem. Mater. 1998, 10, 1355-1365 and references cited therein.
25. Pizzotti, M.; Ugo, R.; Roberto, D.; Bruni, S.; Fantucci, P.; Rovizzi, C. Organometallics 2002, 21, 5830-5840
26. Reyes, H.; Muñoz, B. M.; Farfán, N.; Santillan, R.; Rojas-Lima, S.; Lacroix P.G.; Nakatani, K. J . Mater. Chem. 2002, 12, 2898-2903.
27. Reyes, H.; García, C.; Farfán, N.; Santillá n, R.; Lacroix, P.G.; Lepetit C.; Nakatani, K. J. Organomet. Chem. 2004, 689, 2303-2310.
28. Reyes, H.; Rivera, J. M.; Farfán, N.; Santillan, R.; Lacroix, P. G.; Lepetit C. ; Nakatani, K. J. Organomet. Chem. 2005, 690, 3737-3745.
29. Nauduri, D.; Reddy G. B. S. Chem. Pharm. Bull. 1998, 46, 1254-1260.
30. a) Kukharenko, A. V.; Avramenko., G. V. Russ. J. Gen. Chem. 2001, 71, 1562-1564; b) Daniel, D. S.; Heseltine, D. W. (Eastman Kodak Co.). Fr. Demande (1970), 33 pp. FR 201948219700703 Patent. Priority: US 19680923.
31. Höpfl, H. J. Organomet. Chem. 1999, 581, 129-149.
32. Lacroix, P. G. Eur. J. Inorg. Chem. 2001, 339-348.
33. Sheldrick, G. M.; University of Göttingen: Göttingen (1997).
34. Spek, A. L. J. Appl. Cryst. 2003, 36, 7-13.
35. Farrugia, L. J. Appl. Cryst. 1999, 32, 837-838.
36. Farrugia, L. J. Appl. Cryst. 1997, 30, 565.
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