A Detailed Benchmark and Modeling of the Excited and Emissive States of A Salen Type Tetradentate Schiff Base and Its Zn II Complex: Synthesis, Characterization, Fluorescence and TD-DFT Study

Yıl 2016, Cilt: 44 Sayı: 4, 451 - 461, 01.11.2016

Serkan Demir

Öz

A2:1 condensation of 2-hydroxy naphthaldehyde with 1,3-diaminopropane have resulted symmetrical tet- radentate NNOO Schiff base ligand namely N,N -bis 2-hydroxy-naphthaldimine -2,3-diaminopropane napdap and 1:1 mixing of this ligand with Zn ClO4 2·6H2O in THF yielded the complex N,N -bis 2-hydroxy-naphthaldimine -2,3-diaminopropanato zinc II 1 . Characterizations of the compounds have been carried out by Elemental analyses, IR spectroscopy, Electro-spray ionization mass spectroscopy ESI-MS , Thermal analysis and conductivity measurements. Excited state and emission profiles of the compounds have been investigated by UV-Vis absorbtion spectroscopy and steady state fluorescence spectroscopy techniques. Ver- tical excitations of the compounds responsible for their emissions have been further probed by ab-inito time dependent-density functional theory TD-DFT studies.

Anahtar Kelimeler

Fluorescence spectroscopy, tetradentate Schiff base, TD-DFT, ESI-mass spectroscopy, salen-Zn II complex

Bir Salen Tipi Schiff Bazı ve Zn II Kompleksinin Uyarılmış ve Emisif Hallerinin Ayrıntılı Bir Kıyaslaması ve Modellenmesi: Sentez, Karakterizasyon, Floresans ve TD-DFT Çalışması

Öz

hidroksinaftaldehit ve 1,3-diaminopronanın 2:1 kondenzasyonu sonucu simetrik dörtdişli NNOO Schiff bazı ligantı, N,N -bis 2-hidroksi-naftaldimin -2,3-diaminopropan napdap ve ligantın Zn ClO ·6HO ile THF içerisinde 1:1 karıştırılması ile N,N -bis 2-hidroksi-naftaldimin -2,3-diaminopropanato çinko II kompleksi 1 sentezlendi. Bileşiklerin karakterizasyonları Elementel analiz, IR spektroskopisi, Elektro-sprey iyonlaşma kütle spektroskopisi ESI-MS , Termik analiz and iletkenlik ölçümleri ile yapıldı. Bileşiklerin uyarılmış hal ve emisif özellikleri UV-Vis absorpsiyon spektroskopisi ve kararlı hal floresans spektroskopisi teknikleri ile incelendi. Bileşiklerin emisyonlarından sorumlu dikey uyarılma geçişleri daha ayrıntılı olarak ab-initio zamana-bağlı yoğunluk fonksiyonel teorisi çalışmaları ile incelendi

Anahtar Kelimeler

Floresans spektroskopisi, dört-dişli Schiff bazı, TD-DFT, ESI-kütle spektroskopisi, salen-Zn II compleksi

Kaynakça

• 1. J.M. Bergi, Y. Shi, Science, 271 (1996) 1081.
• 2. W.N. Lipscomb and N. Sträter, Chem. Rev., 96 (1996) 2375-2433.
• 3. J.J.R. Fausto da Silva, R.J.P. Williams, The Biological Chemistry of the Elements: Oxford University Press, New York, 1992.
• 4. G. Jaouen, Bioorganometallics: Biomolecules, Labeling, Medicine, Wiley-VCH, Paris, 2005.
• 5. J.P. Mackay, D.J. Segal, Engineered Zinc Finger Proteins: Methods and Protocols, Springer, New York Heidelberg Dordrecht London, 2010.
• 6. P.D. Boyer, The Enzymes: Hydrolysis: Peptide Bonds, Academic Press, New York and London, 1971.
• 7. H. Chen, Y. Wu, Y. Cheng, H. Yang, F. Li, P. Yang, C. Huang, İnorg. Chem. Commun. 10 (2207) 1413-1415.
• 8. G.K. Andrews, Biometals, 14 (2001) 223-237.
• 9. E.L Que, D.W Domaille and C.J. Chang, Chem. Rev., 108 (2008) 1517-1549.
• 10. B.L. Vallee and K.H. Falchuk, Physiol. Rev., 73 (1993) 79-118.
• 11. C.J. Frederickson, J.Y. Koh, A.I. Bush, Nat. Rev. Neurosci., 6 (2005) 449-462.
• 12. L.C. Costello, R.B. Franklin Mol. Cancer, 5 (2206) 59- 63.
• 13. M. Mager, W.F. McNary, F.J. Lionetti, Histochem. Cytochem., 1 (1953) 493-504.
• 14. C.G. Taylor, Biometals, 18 (2005) 305-312.
• 15. P.D. Zalewski, X. Jian, L.L.L. Soon, W.G. Breed, R.F Seamark, S.F. Lincoln, A.D. Ward, F.Z. Sun, Reprod. Fertil. Dev., 8 (1996) 1097-1105.
• 16. A.I. Bush, W.H. Pettingell, G. Multhaup, M.D. Paradis, J.P.Vonsattel, J.F. Gusella, K. Beyreuther, C.L. Masters, R.E. Tanzi, Science, 265 (1994) 1464-1467.
• 17. A.Q. Truong-Tran, L.H. Ho, F. Chai, P.D. Zalewski, J. Nutr., 130 (2000) 1459S-1466.
• 18. C.J. Frederickson, M.D. Hernandez, J.F. McGinty, Brain Res., 480 (1989) 317-321.
• 19. M.P. Cuajungco, G.J. Less, Neurobiol. Dis., 4 (1997) 137-169.
• 20. D.W. Choi, J.Y. Koh, Annu. Rev. Neurosci., 21 (1998) 347-375
• 21. J.H. Weiss, S.L. Sensi, J.K. Koh, Trends Pharmacol. Sci., 21 (2000) 395-401.
• 22. S.W. Suh, K.B. Jensen, M.S. Jensen, D.S. Silva, P.J. Kesslak, G. Danscher, C.J. Ferederickson, Brain Res., 852 (2000) 274-278.
• 23. A.I. Bush, Alzheimer Dis. Assoc. Disord., 17 (2003) 147-150.
• 24. M.S. Wold, Annu. Rev. Biochem., 66 (1997) 61-62. 25. S. Majumder, L. Mandal, S. Mohanta, İnorg. Chem., 51 (2012) 8739-8749.
• 26. K. Hanaoka, K. Kikuchi, H. Kojima, Y. Urano, and T. Nagano, J. Am. Chem. Soc., 126 (2004) 12470-12476.
• 27. K. Kikuchi, K. Komatsu, T. Nagano, Curr. Opin. Chem. Biol., 8 (2004) 182-191.
• 28. P. Jiang, Z. Guo, Coord. Chem. Rev., 248 (2004) 205- 229.
• 29. S.C. Burdette and S.J. Lippard, Inorg. Chem., 41 (2002) 6816-6823.
• 30. E.N. Jacobsen, in Comprehensive Organometallic Chemistry II (Eds. E.W. Abel, F.G.A. Stone, and E. Willinson, Pergamon, New York, 12 (1995) 1097-1135.
• 31. T.M. Ovitt, G.W. Coates, J. Am. Chem. Soc. 121 (1999) 4072-4073.
• 32. D.A. Atwood, M.J. Harvey, J. Chem. Rev., 101 (2001) 37-52.
• 33. C.T. Cohen, T. Chu, G.W. Coates, J. Am. Chem. Soc., 127 (2005) 10869-10878.
• 34. L. Canali, D.C. Sherrington, Chem. Soc. Rev., 28 (1999) 85-93.
• 35. R.G. Konsler, J. Karl, E.N. Jacobsen, J. Am. Chem. Soc., 120 (1998) 10780-10781.
• 36. A.W. Kleij, M. Kuil, M. Lutz, D.M. Tooke, A.L. Spek, P.C.J. Kamer, P.W.N.M. van Leeuwen, J.N.H. Reek, Inorg. Chim. Acta, 359 (2006) 1807-1814.
• 37. A.W. Kleij, M. Kuil, D.M. Tooke, A.L. Spek, J.N.H. Reek, Chem.-Eur. J., 11 (2005) 4743-4750.
• 38. P.G. Lacroix, Eur. J. Inorg. Chem., (2001) 339-348.
• 39. R. Brissos, D. Ramos, J.C. Lima, F.Y. Mihan, M. Borràs, J. De Lapuente, A. Dalla Cort and L. Rodríguez, New J. Chem. (2013) DOI: 10.1039/c3nj41125g
• 40. S.I. Pascu, P.A. Waghorn, T.D. Conry, B. Lin, H.M. Betts, J.R. Dilworth, R.B. Sim, G.C. Churcill, F.I. Aigbirhio, and J.E. Warren, Dalton Trans., (2008) 2107-2110.
• 41. G. Consiglio, S. Failla, P. Finocchiaro, I.P. Oliveri and S. Di Bella, Dalton Trans., 47 (2012) 387-395.
• 42. A.L. Singer and D.A. Atwood, Inorg. Chim. Acta, 277 (1998) 157-162.
• 43. Y. Gao, J. Wu, Y. Li, P. Sun, H. Zhou, J. Yang, S. Zhang, B. Jin and Y. Tian, J. Am. Chem. Soc., 131 (2009) 5208-5213.
• 44. M. Cano, L. Rodrìguez, J.C. Lima, F. Pina, A. Dalla Cort, C. Pasquini, and L. Schiaffino, Inorg. Chem., 48 (2009) 6229-6235.
• 45. I.P. Oliveri and S. Di Bella, J. Phys. Chem., A 115 (2011) 14325-14330.
• 46. E.C. Escudero-Adán, J. Benet-Buchholz, and A.W. Kleij, Inorg. Chem., 47 (2008) 4256-4263.
• 47. S. Khatua, S.H. Choi, J. Lee, K. Kim, Y. Do, and D.G. Churcill, Inorg. Chem., 48 (2009) 2993-2999.
• 48. Y. Hamada, T. Sano, M. Fujita, T. Fujii, Y. Nishio, K. Shibata, Jpn. J. Appl. Phys., 32 (1993) L511-L513.
• 49. T. Sano, Y. Nishio, Y. Hamada, H. Takahashi, T. Usuki, K. Shibata, K. J. Mater. Chem., 10 (2000) 157-161.
• 50. M.E. Germain, T.R. Vargo, B.A. McClure, J.J. Rack, P.G. Van Petten, M. Odoi, and M.J. Knapp, Inorg. Chem., 47 (2008) 6203-6211
• 51. M.E. Germain and M.J. Knapp, J. Am. Chem. Soc., 130 (2008) 5422-5423.
• 52. M.E. Germain, T.R. Vargo, P.G. Khalifah, and M.J. Knapp, Inorg. Chem., 46 (2007) 4422-4429.
• 53. K.-H Chang, C.-C. Huang, Y.-H. Liu, Y.-H. Hu, P.-T. Chou and Y.-C. Lin, Dalton Trans., (2004) 1731-1738.
• 54. S. Di Bella, N. Leonardi, G. Consiglio, S. Sortino, and I. Fragalà, Eur. J. Inorg. Chem., (2004) 4561-1565.
• 55. G. Consiglio, S. Failla, I.P. Oliveri, R. Purrello and S. Di Bella, Dalton Trans., (2009) 10426-10428.
• 56. Q. Meng, P. Zhou, F. Song, Y. Wang, G. Liu and H. Li, Cryst. Eng. Comm., 15 (2013) 2786-2790.
• 57. W.R. Dawson and M.W. Windsor, J. Phys. Chem., 72 (1968) 3251-3260.
• 58. J.R. Lakowicz, Principles of Fluorescence Spectroscopy: Springer, University of Maryland School of Medicine, Baltimore, Maryland, 2006.
• 59. Gaussian 09, Revision A.1, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J. B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.
• 60. J. Tomasi, M. Persico, Chem. Rev., (1994) 2027-2094.
• 61. J. Tomasi, B. Mennucci, and R. Cammi, Chem. Rev., (2005) 2999-3093.
• 62. N.M. O’Boyle, A.L. Tenderholt and K.M. Langner, J. Comp. Chem., 29 (2008) 839-845.
• 63. S.I. Gorelsky, SWIZARD program, University of Ottawa, Ottawa, Canada, http://www.sg-chem.net/, 2012.
• 64. S.I. Gorelsky, A.B.P. Lever, J. Organomet. Chem., 635 (2001) 187.
• 65. J.F.J. Todd, Pure Appl. Chem., 63 (1991) 1541-1566.