Abstract
Three Ru(II) complexes [Ru(bpy)2(1-IQTNH)](ClO4)2 (1), [Ru(bpy)2(2-QTNH)](ClO4)2 (2) and [Ru(bpy)2(3-IQTNH)](ClO4)2 (3) (bpy = 2,2′-bipyridine, 1-IQTNH = 6-(isoquinolin-1-yl)-1,3,5-triazine- 2,4-diamine, 2-QTNH = 6-(quinolin-2-yl)-1,3,5-triazine- 2,4-diamine, 3-IQTNH = 6-(isoquinolin-3-yl)-1,3,5-triazine-2,4-diamine) have been synthesized and characterized by elemental analysis, 1H NMR spectroscopy, electrospray ionization mass spectrometry and X-ray crystallography. The electrochemical and spectroscopic properties of the complexes differ from those of [Ru(bpy)3]2+ owing to the structural differences between the ligands and their complexes.
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Bazani V, Scandola F, Eds. Supramolecular Photochemistry. Chichester: Ellis Horwood, 1991
Demeunynck M, Bailly C, Wilson WD, Eds. DNA and RNA Binders: From Small Molecules to Drugs. Weinheim: Wiley-VCH, 2003
Gielen M, Tiekink ERT, Eds. Metallotherapeutic Drugs and Metal-Based Diagnostic Agents: The Use of Metals in Medicine. New York: John Wiley & Sons, 2005
Sauvage F, Fischer MKR, Mishra A, Zakeeruddin SM, Nazeeruddin MK, Bauerle P, Graetzel M. A dendritic oligothiophene ruthenium sensitizer for stable dye-sensitized solar cells. ChemSusChem, 2009, 2: 761–768
Juris A, Balzani V, Barigelletti F, Campagna S, Belser P, Von Zelewsky A. Ru(II) polypyridine complexes: Photophysics, photochemistry, electrochemistry, and chemiluminescence. Coord Chem Rev, 1988, 84: 85–279
Balzani V, Juris A, Venturi M, Campagna S, Serroni S. Luminescent and redox-active polynuclear transition metal complexes. Chem Rev, 1996, 96: 756–833
De Cola L, Belser P. Photoinduced energy and electron transfer processes in rigidly bridged dinuclear Ru/Os complexes. Coord Chem Rev, 1998, 177: 301–346
Kaes C, Katz A, Hosseini MW. Bipyridine: The most widely used ligand. A review of molecules comprising at least two 2,2′-bipyridine units. Chem Rev, 2000, 100: 3553–3590
Chao H, Ji LN. DNA interactions with ruthenium(ll) polypyridine complexes containing asymmetric ligands. Bioinorg Chem Appl, 2005, 3: 15–28
Vos JG, Kelly JM. Ruthenium polypyridyl chemistry: From basic research to applications and back again. Dalton Trans, 2006, 4869–4883
Brzozowski Z, Saczewski F, Gdaniec M. Synthesis, structural characterization and antitumor activity of novel 2,4-diamino-1,3,5-triazine derivatives. Eur J Med Chem, 2000, 35: 1053–1064
Jensen NP, Ager AL, Bliss RA, Canfield CJ, Kotecka BM, Rieckmann KH, Terpinski J, Jacobus DP. Phenoxypropoxybiguanides, prodrugs of DHFR-inhibiting diaminotriazine antimalarials. J Med Chem, 2001, 44: 3925–3931
Deans R, Rotello VM. Model systems for flavoenzyme activity. Molecular recognition of flavin at the polymer-liquid interface. J Org Chem, 1997, 62: 4528–4529
Frankamp BL, Uzun O, Ilhan F, Boal AK, Rotello VM. Recognition- mediated assembly of nanoparticles into micellar structures with diblock copolymers. J Am Chem Soc, 2002, 124: 892–893
Sullivan BP, Salmon DJ, Meyer TJ. Mixed phosphine 2,2′-bipyridine complexes of ruthenium. Inorg Chem, 1978, 17: 3334–3341
Case FH, Kennon L. The preparation of triazines and benzimidazoles from 1- and 3-cyanoisoquinolines. J Heterocyclic Chem, 1967, 4: 483–485
Sheldrick GM. SHELXS-97, Program for the Solution of Crystal Structures. University of Göttingen, Germany, 1997
Sheldrick GM. SHELXL-97, Program for Refinement of Crystal Structures. University of Göttingen, Germany, 1997
Murrell JN, Harget AJ. Semiempirical self-consistent-field molecular orbital theory of molecules. New York: Wiley-Interscience, 1971
Hyperchem Release 6.01 for Windows, Hypercube Inc., 2000
Hoffmann R. An extended Hueckel theory. I. Hydrocarbons. J Chem Phys, 1963, 39: 1397–1412
Johnson CK. ORTEP, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976
Rillema DP, Jones DS, Woods C, Levy HA. Comparison of the crystal structures of tris heterocyclic ligand complexes of ruthenium(II). Inorg Chem, 1992, 31, 2935–2938
Perez-Cordero EE, Campana C, Echegoyen L. X-ray structure of [Ru(bpy)3]0: An expanded atom or a new electride? Angew Chem Int Ed Engl, 1997, 36, 137–140
Wang Y, Perez WJ, Zheng GY, Rillema DP, Huber CL. Preparation, purification, and characterization of binuclear ruthenium(II) complexes: Bridging ligands based on diazafluorenes. Inorg Chem, 1998, 37: 2227–2234
Barigelletti F, Juris A, Balzani A, Belser P, Von Zelewsky A. Influence of the ligand structure on the electrochemical and spectroscopic properties of ruthenium(II)-polypyridine complexes. Inorg Chem, 1987, 26: 4115–4119
Boyde S, Strouse GF, Jones WE Jr, Meyer TJ. Effect on MLCT excited states of electronic delocalization in the acceptor ligand. J Am Chem Soc, 1990, 112: 7395–7396
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Chen, Y., Xu, W., Kou, J. et al. Synthesis, crystal structures, electrochemical and spectroscopic properties of ruthenium(II) complexes containing diamino-1,3,5-triazine derivatives. Sci. China Chem. 53, 2099–2105 (2010). https://doi.org/10.1007/s11426-010-4099-4
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DOI: https://doi.org/10.1007/s11426-010-4099-4