Chromatographic separation and characterization of linkage isomers of the 3-(pyridin-2-yl)-1H-1,2,4-triazole complex of ruthenium(II) bis(2,2'-bipyridyl)

Buchanan, Barbara E.; Wang, Renyi; Vos, Johannes G.; Hage, Ronald; Haasnoot, Jaap G.; Reedijk, J.

doi:10.1021/ic00342a048

Cited by 51 publications

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“…In a study carried out by Ryan et al it was found that for ligands with a substituent on the triazole 5-position coordination occurred via both N4 and N2 in a ratio of approximately 9:1, 20 while the ratio of isomers is 1:1 when the 5-position is occupied by a hydrogen atom. 21 With HL1 only one major product was obtained in all cases. To unambiguously determine the coordination mode of the triazole ring in these compounds the X-ray structural analysis of two compounds was performed.…”

Section: X-ray Crystallographymentioning

confidence: 91%

Synthesis and characterisation of ruthenium complexes containing a pendent catechol ring

et al. 2004

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This submission was created using the RSC Article Template (DO NOT DELETE THIS TEXT) (LINE INCLUDED FOR SPACING ONLY -DO NOT DELETE THIS TEXT)A series of [Ru(bipy) 2 L] + and [Ru(phen) 2 L] + complexes where L is 2-[5-(3,4-dimethoxyphenyl)-4H-1,2,4-triazol-3-yl]pyridine (HL1) and 4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)benzene-1,2-diol (HL2) are reported. The compounds obtained have been characterised using x-ray crystallography, NMR, UV/Vis and emission spectroscopies. Partial deuteriation is used to determine the nature of the emitting state and to simplify the NMR spectra. The acid-base properties of the compounds are also investigated. The electronic structure of the HL1 complex is examined using ZINDO. Electro and spectroelectrochemical studies on [Ru(bipy) 2 (L2)] + suggest that proton transfer between the catechol and triazole moieties on L2 takes place upon oxidation of the L2 ligand. IntroductionThe hydroquinone/quinone redox couple plays an essential role as electron mediator in the charge separation processes in photosynthesis. 1 As a result there has been extensive interest in the redox properties of quinone containing metal complexes and in their potential to act as electron acceptors or donors. 2 In these studies catechol based ligands are coordinated to a wide range of metals. 3 Much less attention has been paid to the interaction between metal centres and pendent hydroquinone/quinone groupings, although such materials may participate in light induced electron transfer reactions. 4 We are presently involved in a systematic study of the electrochemical and photophysical properties of ruthenium complexes containing pendent hydroquinone/quinones. 5,6 In an earlier study on ruthenium polypyridyl complexes incorporating pyridyltriazole ligands with free hydroquinone groupings, electrochemically induced intramolecular protonation of the ruthenium centre was observed upon oxidation of the hydroquinone moiety. 6 In this contribution the synthesis and deprotection of the methoxy complexes [Ru(bipy) 2 (L1)]PF 6 .5H 2 O and [Ru(phen) 2 (L1)]PF 6 .2H 2 O (where HL1 is 2-[5-(3,4-dimethoxyphenyl)-4H-1,2,4-triazol-3-yl]pyridine) to produce the catechol type complexes with the ligand HL2 4-(5-Pyridin-2-yl-4H-1,2,4-triazol-3-yl)benzene-1,2-diol are described (for ligand structures see Figure 1). The partially deuteriated analogues [Ru(d 8 -bipy) 2 (L1)] + and [Ru(d 8 -phen) 2 (L1)] + are also described. The materials obtained have been characterised by X-ray crystallography and 1 H-NMR spectroscopy. The absorption, emission, photophysical and electrochemical properties of the complexes are also examined. To aid interpretation of the results obtained, semi-empirical calculations using ZINDO were carried out on [Ru(bipy) 2 (HL1)] 2+ and [Ru(bipy) 2 (L1)] + , where the triazole moieties are in the protonated and deprotonated states respectively. ExperimentalAll synthetic reagents were of commercial grade and used without further purification. The solvents used in spectroscopic measurements were HPLC grade. Perdeute...

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Section: X-ray Crystallographymentioning

confidence: 91%

Synthesis and characterisation of ruthenium complexes containing a pendent catechol ring

et al. 2004

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“…This is in contrast with the behaviour of most common triazole complexes. [16,17] 2-D COSY spectroscopic techniques were used to assign the 1 H resonances where possible. The doublets observed at δ ϭ 9.75 and 9.42 can be attributed to the protons at positions a and c of the phenanthroline ring A respectively.…”

Section: Resultsmentioning

confidence: 99%

Rhodium Mediated N−O Bond Formation

Burke

Gallagher

Indelli

et al. 2002

Eur. J. Inorg. Chem.

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Reaction of [Rh(phen)2Cl2]Cl (phen = 1,10‐phenanthroline) with the ligand 3,5‐bis(pyridin‐2‐yl)‐1,2,4‐triazole (Hbpt) in H2O at pH 9 gives rise to the formation of a single stable compound. Single‐crystal X‐ray analysis of this material reveals that in the product obtained an oxygen atom has been inserted between the Rh(phen)2 moiety and the triazole ring of the bpt ligand yielding a compound of the type [Rh(phen)2(Obpt)](PF6)2·0.767CH3CN·0.28H2O. Insertion of oxygen in this manner has not been reported previously. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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“…The multicoordination capability of the triazole segment has induced formation of several isomers during reaction with the [Ru(bpy) 2 ] unit. As a consequence, effective chromatographic techniques were needed to separate these coordination isomers [22] .…”

Section: Ligand Modifi Cationsmentioning

confidence: 99%

Pyridyl Azolate Based Luminescent Complexes: Strategic Design, Photophysics, and Applications

Chi

Chou

2007

Highly Efficient OLEDs With Phosphorescent Materials

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This chapter summarizes the deliberate design of the chelating C -linked 2 -pyridyl azolate ligands. Attempts have been made in ligand functionalization and modification to fi ne -tune the photophysical properties of the associated metal complexes. Moreover, this chapter also reports the synthetic strategies, leading to a series of high emissive, boron as well as osmium, ruthenium, iridium, and platinum metal complexes, which all possess at least one 2 -pyridyl azolate chromophore. Spectroscopic and dynamic measurements, in combination with theoretical analyses, have thus gain much insight into their electronically excited state properties such as the energy gap and nature of the lowest lying excited states, mechanism of intersystem crossing, and the effi ciency of corresponding radiative decay and nonradiative deactivation processes. From the application point of view, efforts have been made to the exploitation of these emitting materials as dopants for preparation of high effi ciency, true -blue and saturated -red polymer light -emitting diodes (PLEDs), and organic light -emitting diodes (OLEDs). IntroductionThe transition -metal complexes incorporating simple diimine ligands [1] such as 2,2 ′ -bipyridine (bpy) and/or cyclometalated ligands [2] such as 2 -phenyl pyridine (ppy) have attracted a great interest in recent years. Research work in this area was principally motivated by the use of these complexes in the study of excitedstate electron and energy transfer [3] as well as the potential applications in the fabrication of chemical sensors, photovoltaics and organic light -emitting diodes (OLEDs) [4] .

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Chromatographic separation and characterization of linkage isomers of the 3-(pyridin-2-yl)-1H-1,2,4-triazole complex of ruthenium(II) bis(2,2'-bipyridyl)

Abstract: Chromatographic Separation and Characterization of LinkageIsomers of the 3-(Pyridin-2-yl)-l//-l,2,4-triazole Complex of Ruthenium(II) Bis(2,2-bipyridyl)

Cited by 51 publications

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Synthesis and characterisation of ruthenium complexes containing a pendent catechol ring

Synthesis and characterisation of ruthenium complexes containing a pendent catechol ring

Rhodium Mediated N−O Bond Formation

Pyridyl Azolate Based Luminescent Complexes: Strategic Design, Photophysics, and Applications

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