Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Electrochemical and Fluorescent Properties of Ferrocenyl Chalcones Containing 1-Naphthalenyl Group: X-ray Crystal Structure of Fc-C(O)CH=CH-(1-Naph)

  • Suh, Woo-Young (Department of Chemistry, Seoul Women's University) ;
  • Jeon, Hyo-Kyung (Department of Chemistry, Seoul Women's University) ;
  • Lee, Ji-Yeon (Department of Chemistry, Seoul Women's University) ;
  • Lim, Chae-Mi (Department of Chemistry, Seoul Women's University) ;
  • Lee, Su-Kyung (Department of Chemistry, Seoul Women's University) ;
  • Noh, Dong-Youn (Department of Chemistry, Seoul Women's University)
  • Received : 2011.11.17
  • Accepted : 2011.11.29
  • Published : 2012.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Ferrocenyl chalcones (Fc-C(O)CH=CH-Ar: Fc-Ar) with mono- and di-1-naphthalenyl moieties (Fc-1Naph and Fc-d1Naph) were prepared and spectroscopically characterized. The enone bridge was in the s-cis conformation and the $\pi$-electrons on the C=C bond were further delocalized on the bridge. The naphthalenyl moiety deviates greatly from the enone-Cp plane by $26.9(1)^{\circ}$. Cyclic voltammetry measurements for Fc-1Naph exhibit one reversible cycle for the redox of the ferrocenyl moiety at a lower potential, and one irreversible oxidation peak at the higher potential region. For Fc-d1Naph, the cyclic voltammogram is more featureless. Fluorescence properties for both compounds are active in polar solvents with $\lambda_{em}$ = 500 nm (EtOH) and $\lambda_{em}$ = 512 nm (MeOH) for Fc-1Naph and $\lambda_{em}$ = 496 nm (EtOH) and $\lambda_{em}$ = 508 nm (MeOH) for Fc-d1Naph. The intensity of Fc-d1Naph is more than twice than that of Fc-1Naph. The fluorescence properties for both compounds are inactive in the less polar solvents such as $CH_3CN$, $CH_2Cl_2$ and $CHCl_3$.

Keywords

References

  1. Zsoldos-Mady, V.; Csampai, A.; Szabo, R.; Meszaros-Alapi, E.; Pasztor, J.; Hudecz, F.; Sohar, P. Chem. Med. Chem. 2006, 1, 1119. https://doi.org/10.1002/cmdc.200600052
  2. Wu, X.; Wilairat, P.; Go, M. L.; Bioorg. Med. Chem. Lett. 2002, 12, 2299. https://doi.org/10.1016/S0960-894X(02)00430-4
  3. Liu, M.; Wilairat, P.; Go, M. L. J. Med. Chem. 2001, 44, 4443. https://doi.org/10.1021/jm0101747
  4. Wu, X.; Tiekink, E. R. T.; Kostetski, I.; Kocherginsky, N.; Tan, A. L. C.; Khoo, S. B.; Wilairat, P.; Go, M. L. Eur. J. Pharm. Sci. 2006, 27, 175. https://doi.org/10.1016/j.ejps.2005.09.007
  5. Attar, S.; O'Brien, Z.; Alhaddad, H.; Golden, M. L.; Calderon- Urrea, A. Bioorg. Med. Chem. 2011, 19, 2055. https://doi.org/10.1016/j.bmc.2011.01.048
  6. Kawabe, Y.; Ikeda, H.; Sakai, T.; Kawasaki, K. J. Mater. Chem. 1992, 2, 1025. https://doi.org/10.1039/jm9920201025
  7. Sens, R.; Drexhage, K. H. J. Lumin. 1981, 24-25, 709. https://doi.org/10.1016/0022-2313(81)90075-2
  8. Delavaux-Nicot, B.; Maynadie, J.; Lavabre, D.; Lepetit, C.; Donnadieu, B. Eur. J. Inorg. Chem. 2005, 2493.
  9. Delavaux- Nicot, B.; Maynadie, J.; Lavabre, D.; Fery-Forgues, S. J. Organomet. Chem. 2007, 692, 874. https://doi.org/10.1016/j.jorganchem.2006.10.045
  10. Delavaux-Nicot, B.; Fery-Forgues, S. Eur. J. Inorg. Chem. 1999, 1821.
  11. Son, K. I.; Noh, D. Y. J. Korean Chem. Soc. 2007, 51, 591. https://doi.org/10.5012/jkcs.2007.51.6.591
  12. CCDC 836352.
  13. Lee, S. K.; Lim, C. M.; Lee, J. Y.; Noh, D. Y. Bull. Korean Chem. Soc. 2011, 32, 321. https://doi.org/10.5012/bkcs.2011.32.1.321
  14. Jung, Y. J.; Son, K. I.; Oh, Y. E.; Noh, D. Y. Polyhedron 2008, 27, 861. https://doi.org/10.1016/j.poly.2007.11.015
  15. Son, K. I.; Kang, S. Y.; Noh, D. Y. Bull. Korean Chem. Soc. 2009, 30, 513. https://doi.org/10.5012/bkcs.2009.30.2.513
  16. Son, K. I., Ph.D. Thesis, Seoul Women's University, Seoul, 2008.
  17. Lee, S. K.; Noh, Y. S.; Son, K. I.; Noh, D. Y. Inorg. Chem. Commun. 2010, 13, 1343. https://doi.org/10.1016/j.inoche.2010.07.032
  18. Sheldrick, G. M. SHELXTL, ver. 5, Bruker AXS, Madison, Wisconsin, 1995.
  19. Fery-Forgues, S.; Delavaux-Nicot, B. J. Photochem. Photobio. A: Chem. 2000, 132, 137. https://doi.org/10.1016/S1010-6030(00)00213-6
  20. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley: Weinheim, Germany, 2003.
  21. Reichardt, C. Chem. Rev. 1994, 94, 2319. https://doi.org/10.1021/cr00032a005

Cited by

  1. Ferrocenyl Chalcones with 1- and 2-Naphthalenyl Group: Spectroscopic Characterizations and Electrochemical Properties vol.58, pp.5, 2012, https://doi.org/10.5012/jkcs.2014.58.5.496
  2. Ferrocenyl-cymantrenyl hetero-bimetallic chalcones: Synthesis, structure and biological properties vol.1085, pp.None, 2012, https://doi.org/10.1016/j.molstruc.2014.12.070
  3. Synthesis of Ferrocene Tethered Heteroaromatic Compounds Using Solid Supported Reaction Method, their Cytotoxic Evaluation and Fluorescence Behavior. vol.4, pp.15, 2012, https://doi.org/10.1002/slct.201901088