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Synthesis and Photophysical Application of Functionalised 2,2':6',2"-Terpyridine Metal Complexes. A review

Author Affiliations

  • 1Department of Chemistry, Gandhi Institute For Technology, Bhubaneswar, Odisha, INDIA
  • 2 Department of Chemistry, Utkal University, Bhubaneswar, Odisha, INDIA

Res.J.chem.sci., Volume 4, Issue (10), Pages 85-89, October,18 (2014)

Abstract

This report outlines the progress to date in preparing derivatives of 2,2':6',2"-Terpyridine and its metal complexes that shows spectroscopic and luminescence properties. Derivatives investigated are of the type 4’-Functionalized- 2,2’:6’,2’’-Terpyridines, 4-(4-bromomethyl phenyl)-2,2:6,2-terpyridine, 4’-aryl-2,2’:6’,2’’-terpyridines,1,3-bis(2,2’:6’,2’’-terpyridin-4’-yl)benzene dichloromethane solvate. and 5,5’’-bis (hydroxytetramethylenoxy methyl)-2,2’:6’,2’’-terpyridine.The reported papers having complexes of these ligands with different metal ions like Co(II),Co(III),Cr(III),Ni(II),Cu(II), Pt(II),Ru(II),Ir(II),Pd(II),Fe(II),Zn(II) have been reviewed. The photophysical applications of these ligands and their metal complexes are of the type construction of photochemical molecular devices, photosensitized component, Colorimetric and Luminescence pH Sensors, supramolecular recognition centers, biosensor etc. which has been reported by different authors are also reviewed.

References

  1. Morgan G. T. and Burstall F. H., Dehydrogenation of pyridine by anhydrous ferric chloride, J. Chem. Soc. , 20-30 (1932)
  2. Krohnke F.The Specific Synthesis of Pyridines and Oligopyridines, Synthesis, (1) ,1–24. (1976)
  3. Neve F., Crispini A., Campagna S., Inorg. Chem., (36),6150–6256, (1997)
  4. Jantunen K.C., Scott B.L., Dearomatization and Functionalization of Terpyridine by Lutetium (III) Alkyl Complexes, J. Am. Chem. Soc,(128), 6322–6323, (2006)
  5. Lehn J.M., Supramolecular Chemistry, Concepts and Perspectives. , VCH: Weinheim, (1995)
  6. Chelucci G., Thummel R. P., Chiral 2,2-bipyridines, 1,10-phenanthrolines, and 2,2:6,2-terpyridines: Syntheses and applications in asymmetric homogeneous catalysis, Chem. Rev., (102) 3129–3170, ( 2002)
  7. Islam A., Sugihara H., Arakawa H. J., Molecular design of ruthenium(II) polypyridyl photosensitizers for efficient nanocrystalline TiO2 solar cells, Photochem. Photobiol. A, (158), 131–138, ( 2003)
  8. Clarke M., Ruthenium metallopharmaceuticals, J. Coord. Chem. Rev., (236), 209–233, (2003)
  9. Belluco U., Bertani R., Michelin R.A. and Mozzon M., Platinum-alkynyl and alkyne complexes: old systems with new chemical and physical perspectives,J. Organomet. Chem., (600), 37-55,( 2000)
  10. Atkins P. W., The Elements of Physical Chemistry 2nd Ed., Oxford University Press, (1999)
  11. Andres P. R., Lunkwitz R., Pabst G. R., Bφhn K., New 4’-Functionalized 2,2’:6’,2’’-Terpyridines for Applications in Macromolecular Chemistry and Nanoscience, Eur. J. Org. Chem., 3769-3776, ( 2003)
  12. Yin X. H., Synthesis of Terpyridine Derivatives Containing -Cyclodextrin, Chinese Chemical Letters, (14), 445 – 447, (2003)
  13. Tu S., Jia R., Jiang B., Zhang J., Zhang Y., Yao C.. and Ji S., Krohnke reaction in aqueous media: one-pot clean synthesis of 4’-aryl-2,2’:6’,2’’-terpyridines, Tetrahedron, (63) 381–388, (2007)
  14. Siemelinga U., Der Br¨uggena J. V., Vorfelda U., Stammlerb A., and Stammlerb H.G., Large Scale Synthesis of 4’-(4-Bromophenyl)-2,2’:6’,2”-terpyridine and Nature of the Mysterious Green By-product Z., Naturforsch., (58b), 443 – 446 , (2003)
  15. Ulrich S. S., Christian E., Christian H. W., Synlett , Synthesis of 5,5’’-bisfunctionalized 2,2’:6’,2’’-Terpyridines using functionalized pyridine building blocks, (3), 342-344.(1999)
  16. Vaduvescu S. and Potvin P.G., 1,3-Bis (2,2’’:6’,2’’-terpyridin-4’-yl) benzene, a new dinucleating bis tridentate) ligand, as its dichloromethane solvate , Acta Cryst. (E59), 483-484(2003)
  17. Korall P., Borje A., Norrby P.O., Akermark B., High Yield Preparation of 4'-(4-Bromophenyl)-2,2':6',2"-terpyridine by a Condensation Reaction. Determination of the Stereochemistry of Two Complex By-products by a Combination of Molecular Mechanics and NMR Spectroscopy., Acta Chemica Scandinavica , (51)760-766(1997)
  18. Hissler M., El-ghayoury A., Harriman A., and Ziessel R., Fine-Tuning the Electronic Properties of Binuclear Bis(terpyridyl)ruthenium(II) Complexes Angew. Chem. Int. Ed., (37), 1717-1720,( 1998)
  19. Davidson G. J. E., Loeb S. J., Passaniti P., Silvi S., and Credi A., Wire-Type Ruthenium(II) Complexes with Terpyridine-Containing [2]Rotaxanes as Ligands: Synthesis, Characterization, and Photophysical Properties , Chem. Eur. J., (12), 3233 – 3242,( 2006)
  20. Gonzαlez A. D., Yatsimirsky A. K.., Binding of ureas and amides to a Cu(II) terpyridine complex in methanol , Inorganica Chimica Acta, (363) 270–274, (2010)
  21. Cini R. and Pifferi C., Supramolecular networks via hydrogen bonding and stacking interactions for adenosine 5’-diphosphate., J. Chem. Soc., Dalton Trans., 699–710, (1999)
  22. Uma V., Elango M., and Nair U. B., Copper(II) Terpyridine Complexes: Effect of Substituent on DNA Binding and Nuclease Activity, Eur. J. Inorg. Chem., 3484–3490, (2007)
  23. Kapoor S. and Sastry M.S., Fluorescent zinc–terpyridine complex containing coordinated peroxo counter ion in aqueous medium , Proc. Indian Acad. Sci. (Chem. Sci.), (112), 459–463, (2000)
  24. Laine P.΄, Bedioui F., Ochsenbein P., Marvaud V., Bonin M.,and Amouyal E., A New Class of Functionalized Terpyridyl Ligands as Building Blocks for Photosensitized Supramolecular Architectures. Synthesis, Structural, and Electronic Characterizations, J. Am. Chem. Soc., (124), 1364-1377,(2002)
  25. Yoshikawa N., Matsumura T., Electrochemical and phosphorescent properties of new mixed ligand Ir(III) complexes coordinated with both terpyridine and various bipyridine derivatives, Analytical sciences, (19),761-765, (2003)
  26. Hofmeier H., Hoogenboom R., Wouters M.E.L., and Schubert U.S., High Molecular WeightSupramolecular Polymers Containing Both Terpyridine Metal Complexes and Ureidopyrimidinone Quadruple Hydrogen-Bonding Units in the Main Chain , J. Am. Chem. Soc., (127), 2913-2921, (2005)
  27. Cock P.A., Cottrellan C.E., Boyd R.K., Rates of Reaction of Nickel (II) with Terpyridine in Dimethyl Sulfoxide, Canadian Journal of Chemistry, 50(3) ,402-411, (1972)
  28. Ramdeehul S., Barloy L., and Osborn J.A., Synthesis, Solution Dynamics, and Crystal Structures of (2,2‘:6‘,2‘‘-Terpyridine) (η1- and η3-allyl)palladium(II) Complexes, Organometallics, 15(26), 5442-5444, (1996)
  29. Indumathy R., Kanthimathi M., Weyhermuller T., Nair B.U., Cobalt complexes of terpyridine ligands: Crystal structure and nuclease activity, Polyhedron , 17(27), 3443–3450, (2008)
  30. Liu R., Li Z., Zhu H., Sun W., Synthesis and photophysical studies of back-to-back dinuclear platinum terpyridine complexes with different substituents on the bridging ligand , Inorganica Chimica Acta, (387), 383-389, (2012)
  31. Santoni M.P., Medlycott E.A., Hanan G.S. , Hasenknopf B., Proust A., Nastasi F., Campagna S. Chiorboli C. , Argazzid R. and Scandola F., Photoinduced energy transfer in a rod-like dinuclear Ru(II) complex containing bis-pyridyl-1,3,5-triazine ligands, Dalton Trans.,(20), 3964–3970, (2009)
  32. Usami N., Furusawa Y., Kobayashi K., Frohlich H., Lacombe S., Le S. C., Int. J. Radiat. Biol., (81), 515-518,(2005)
  33. Arena G., Scolaro L. M., Pasternack R. F., Romeo R., Synthesis, Characterization, and Interaction with DNA of the Novel Metallointercalator Cationic Complex (2,2':6',2'' terpyridine)methylplatinum(II), Inorg. Chem., 34(11), 2994-3002, (1995)
  34. Wong K.M.C., Tang W.S., Lu X.X., Zhu N. and Yam V.W.,Functionalized Platinum(II) Terpyridyl Alkynyl Complexes as Colorimetric and Luminescence pH Sensors, Inorganic Chemistry, 44(5), 1492-1498, ( 2005)
  35. Scott M. B., Anthony J. Z., Ronnie L. P., Vazquez D., Wilson A., and Uwe H. F. B., Terpyridine-Based Cruciform-Zn (II) Complexes as Anion-Responsive Fluorophore, Organic letters, (9), 4519-4522, (2007)
  36. Santoni M.P. , Hanan G.S. , Hasenknopf B., Proust A., Nastasi F., Serronic S. and Campagna S., Dinuclear Ru(II) complexes of bis-(dipyrid-2-yl)triazine (bis-dpt) ligandsas efficient electron reservoirs, Chem. Commun., (47), 3586–3588, (2011)
  37. Tsuboyama A., Takiguchi T., Okada S., Osawa M., Hoshino M., Ueno K., A novel dinuclear cyclometalated iridium complex bridged with 1, 4-bis [pyridine-2-yl] benzene: its structure and photophysical properties, Dalton Trans., (8), 1115-1116, (2004)