cas 123640-38-0, 2,6-Di(1-pyrazolyl)pyridine

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New energetic Silver(I) complexes with Nnn type Pyrazolylpyridine ligands and oxidizing anions
The high energy complexes [Ag (pp) (NO3)] (I), [Ag (dmpp) (NO3)] (II), [Ag (pp)ClO3)] (III), [Ag (dmpp) (ClO3)] (IV), [Ag (pp) (ClO4)] (V), [Ag (dmpp) (ClO4)] (VI) were synthesized from the ligands, Bis-2,6(Pyrazol-1-yl)Pyridine (pp) and Bis-2,6 (3,5-dimethylpyrazol-1-yl)Pyridine (dmpp). They were characterized via IR spectroscopy and elemental analysis. Suitable single crystals of complexes I, IV and VI have been obtained and their molecular structures were determined by X-Ray diffraction methods. The X-Ray study revealed that these complexes were di-nuclear. All complexes have been analyzed by TG-DTA. It was determined that they decompose exothermically in explosive reactions. Elevation in the thermal decomposition temperature, enthalpy of reaction and mass loss was observed with increasing number of oxygens within the anion in the complex structure. The HOMO and LUMO energy levels of the complexes, together with the theoretical formation enthalpies, were calculated by using Gaussian 09 software package whereas the enthalpies of thermal decomposition were measured by DSC. The products of decomposition were predicted from the theoretical formation enthalpy and the measured heat of reaction values according to Hess’ law. It was observed that the thermogravimetry plots of complexes I, II and VI were suitable for thermo-kinetics investigation. Thus, they were analyzed by means of isothermal (Coats-Redfern) and non-isothermal-isoconvertional (Flyn-Ozawa-Wall and Kissinger-Akahira-Sunose) methods and certain thermodynamic parameters were calculated. It was discovered that all complexes except complex II decomposed with rapid, single step reactions whereas complex II decomposed with a 2-step reaction.
Atakol, Arda,Atakol, Orhan,Dal, Hakan,Naz?r, Hasan,Svoboda, Ingrid
(2020)
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Synthesis, crystal structure, and thermal decomposition of two Co(II) complexes with NNN pyrazolyl type ligand and pseudo-halogen
The Co(II) complexes I and II were prepared in nonaqueous solvents containing cyanate with pyrazolylpyridine ligands, namely, bis-2,6-(pyrazol-1- yl) pyridine (Pp) and bis-2,6-(3,5-dimethyl-pyrazol- 1-yl) pyridine (Dmpp), respectively. These complexes were characterized with elemental analysis, IR spec- troscopy, and X-ray diffraction techniques. X-ray diffraction study revealed that complex I was mononuclear and complex II was dinuclear and ionic. The ionic complex II has an octahedral cationic coordination sphere and a tetrahedral anionic coordination sphere. Thermogravimetry results showed that the thermal decompo- sition is starting with the carbon content of the pyrazolyl rings. Pleiades Publishing, Ltd., 2013.
Oez,Yilmaz,Arici,Svoboda,Akay,Atakol
p. 829 - 835
(2013)
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Experimental and theoretical investigation of the spectroscopic and electronic properties of pyrazolyl ligands
The electronic and spectroscopic properties of seven pyrazole derivatives are presented in order to give a clear understanding of their distinguishing features. Four out of the seven ligands are synthesised and are also characterised experimentally. A very high correlation was observed between the experimental and the theoretical IR, 1H NMR and 13C NMR, which help in the characterisation of the ligands. The excitation properties computed using the TDDFT shows that most of experimentally observed absorptions of the ligands are predominantly form either the HOMO or HOMO-1 to LUMO or LUMO+1. The characteristic features of the *N atoms (i.e. metal available coordinating centre) shows that the carboxylic unit may possibly decrease the metal affinity of the pyrazole unit while the pyridine unit will increase the affinity. The conductivity properties of the seven ligands are found to be in the order of bdmpzpy > bpzpy > bphpza > bdcpzpy > phpz > dcpz. The J-coupling of *NN can give an insight into the variation in their bond distance, bond stretch and bond strength in the ligands. Also the atomic properties of the *N atoms and their *NN bonds can help in the molecular characterisation, differentiation and in prediction of the non-linear optical properties of the ligands as conductive materials.
Adeniyi, Adebayo A.,Ajibade, Peter A.
p. 831 - 845
(2014)
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One-step synthesis of symmetrically substituted 2,6-bis(pyrazol-1-yl) pyridine systems
A one-pot synthetic route that allows functionalization of the 2,6-bis(pyrazol-1-yl)pyridine backbone in the 4- and 4″-pyrazole positions by direct H(4)-pyrazole halogen exchange is described. The diiodo derivative in particular provides easy access to additional functionalities through both Sonogashira and Grignard exchange reactions. These synthons represent optimal building blocks for the extension of the chelating core and for the assembly of rigid organic and metalloorganic nanostructures. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Zoppellaro, Giorgio,Baumgarten, Martin
p. 2888 - 2892
(2005)
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Luminescent Electropolymerizable Ruthenium Complexes and Corresponding Conducting Metallopolymers
Tris(2,2′-bipyridyl)ruthenium(II) dichloride [Ru(bpy)3Cl2] and analogous complexes have been studied extensively in the literature due to their luminescent and photochemical properties as well as their excited-state lifetimes. Conducting polymers with similar ruthenium groups have also been investigated for various applications. In this study, syntheses of four ruthenium complexes with a polymerizable tridentate ligand, bis[4-[2-(3,4-diethylenedioxy)thiophene]pyrazol-1-yl]pyridine (EDOT2NNN), and with bidentate ligands, two of which were anionic (hfac: 1,1,1,5,5,5-hexafluoro-2,4-pentanedione; dbm: dibenzoylmethane) and two of which were neutral (bpy: 2,2′-bipyridyl; phen: 1,10-phenanthroline), were achieved for potential OLED/PLED applications. Saturated CH2Cl2 solutions of monomers were oxidatively and electrochemically polymerized, and the scan rate dependences of the polymers were measured. UV-vis spectroscopic characterizations of the complexes and the EDOT-functionalized ligand were obtained. [Ru(EDOT2NNN)(phen)(Cl)](PF6) was electropolymerized on an ITO (indium tin oxide)-coated glass surface to obtain the solid-state absorption spectrum of the corresponding polymer. Photophysical data for each complex, i.e., excitation and emission spectra at 77 K and RT, in EtOH/MeOH (4:1) and in 2-MeTHF (dry, air-free, and aerated), quantum yield, and luminescence lifetime have been measured. The radiative and nonradiative decay constants as well as the oxygen quenching rate coefficient for each complex were calculated. [Ru(EDOT2NNN)(phen)(Cl)](PF6), having the highest quantum yield of phosphorescence and the longest lifetime, was electropolymerized on an ITO-coated glass surface to obtain the solid-state excitation and emission spectra of the corresponding polymer. Luminescence studies of the polymer had promising results for photoluminescence.
Keskin, Seyma Goren,Zhu, Xunjin,Yang, Xiaoping,Cowley, Alan H.,Holliday, Bradley J.
p. 8217 - 8228
(2018)
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New energetic copper(II) complexes with pyrazolyl type ligands
Nine CuII complexes (I-IX) containing the azide ion and bis-2,6-(pyrazol-1-yl)pyridine (pp), bis-2,6-(pyrazol-1-yl)pyridine (dmpp), and 2-(pyrazol-1-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine (mpp), which are derivatives of pyrazolylpyridine, were prepared in nonaqueous medium. These complexes were characterized by elemental analyses and IR spectroscopy. Crystals of one of these complexes [CumppClN3 (VII)] were prepared in suitable size, and a molecular structure of this complex was obtained with X-ray diffraction method. Complexes were examined by thermogravimetry and differential scanning calorimetry methods. Thermal decomposition was observed in complexes including two azide groups similar to that seen in explosives. In the complexes containing one azide group, formation of the CuI complexes was observed after thermal decomposition of the azide group.
Oez, Sevi,Svoboda, Ingrid,Kurtaran, Raif,Aksu, Mecit,Sari, Musa,Kunduraci, Melike,Atakol, Orhan
p. 257 - 262
(2011)
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Flexible and optically transparent polymer embedded nano/micro scale spin crossover Fe(II) complex patterns/arrays
A novel highly soluble spin-crossover (SCO) [FeII(L) 2](BF4)2 complex (I) was prepared, where L = 4,4″-dioctylated 2′,6′-bispyrazolylpyrine. Complex I shows reversible temperature dependent SCO behavior with a T1/2 centered around 270 K. Exploiting the high solubility and hence superior processability of complex I nano/micro scale arrays and square patterns were fabricated on a glass substrate. Additionally, for the first time, for the possible flexible technological applications, the SCO arrays (area: 2 mm2) were successfully embedded within an optically transparent thin polystyrene film and studied using Raman spectroscopy/imaging technique. Variable temperature Raman spectroscopy studies further confirmed the SCO behavior of complex I.
Basak, Supratim,Hui, Pramiti,Chandrasekar, Rajadurai
p. 3408 - 3413
(2013)
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Synthesis, characterization, and cycloaddition reaction studies of zinc(II) acetate complexes containing 2,6-bis(pyrazol-1-yl)pyridine and 2,6-bis(3,5-dimethylpyrazol-1-yl)pyridine ligands
The complexes [Py(Pz)2]Zn(OC([dbnd]O)Me)2(1) and [Py(Me2Pz)2]Zn(OC([dbnd]O)Me)2(2), where ligands Py(Pz)2and Py(Me2Pz)2are tridentate 2,6-bis(pyrazol-1-yl)pyridine and 2,6-bis(3,5-dimethylpyrazol-1-yl)pyridine, respectively, have been synthesized and characterized. The single crystal X-ray diffraction analysis confirmed compound 2 to be monomeric with six-coordinate zinc center. In addition to tridentate ligand Py(Me2Pz)2, both κ1-acetate and κ2-acetate ligands are ligated to zinc metal atom in 2. The synthesized complexes 1 and 2 were used as effective catalysts for the cycloaddition between CO2and epoxides in the presence of various kinds of cocatalysts such as n-Bu4PBr, n-Bu4NI, n-Bu4NBr, n-Bu4NCl, PPNCl, and DMAP under the condition of 75 °C, 10 bar CO2pressure, 0.1 mol% catalyst loading, and 24 h. The reaction temperature, CO2pressure, and catalyst loading ratio applied in this study are somewhat milder condition than those for other reported zinc-based catalysts. In addition, 1/n-Bu4PBr system showed the best catalytic activity for the cycloaddition of CO2to propylene oxide, which showed the highest reactivity among seven other kinds of epoxides.
Shin, Min Seok,Oh, Beom Jin,Ryu, Ji Yeon,Park, Myung Hwan,Kim, Min,Lee, Junseong,Kim, Youngjo
p. 101 - 106
(2017)
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Biphenyl bridged hexadentate N6-ligands-a rigid ligand backbone for Fe(ii) spin crossover complexes
The novel hexadentate nitrogen based ligand N,N′-bis-(2-(1H-pyrazol- 1-yl)pyridine-6-ylmethyl)-2,2′-biphenylenediamine (3) was synthesized and used for the preparation of iron Spin Crossover (SCO) complexes [Fe(3)][BF 4]2 (4) and [Fe(3)][ClO4]2 (5), which differ only by the respective counter ion. These complex salts show different spin transition temperatures T1/2 (135 and 157 K, respectively). This effect was studied by the investigation of the solid state structure of different low- and high-spin isomers. All complexes of this series show closely related crystal packing regardless of the counter ion, metal (Zn/Fe) and spin state. The isomer exhibiting the lower transition temperature (4) was also investigated in respect to its photomagnetic behaviour. The LIESST process could be monitored for this complex, but no reverse-LIESST was observed. The relaxation of the photo-induced state occurs at ca. 80 K, showing a complex, three-state relaxation mechanism.
Heider, Silvio,Petzold, Holm,Chastanet, Guillaume,Schlamp, Stephan,Rueffer, Tobias,Weber, Birgit,Letard, Jean-Francois
p. 8575 - 8584
(2013)
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Transition metal chlorides are lewis acids toward terminal chloride attached to late transition metals
Two different neutral tridentate imine-donor pincer ligands interact with excess MCl2 (M = Co or Cu) to form compounds of the same stoichiometry, (LMCl2)2·MCl2, where the assembling force is the electron richnes
Hui, Alice K.,Cook, Brian J.,Mindiola, Daniel J.,Caulton, Kenneth G.
p. 3307 - 3310
(2014)
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(Acetonitrile) [2,6-bis(pyrazol-1-yl)-pyridine](isonicotinamide)copper(II)-tetrafluoroborate-ac etonitrile (1/2/2)
The crystal structure of the compound [Cu(C2H3N)(C11H9N5) (C6H6N2O)](BF4)2 ·2C2H3N was discussed. It was found that the compound consists of cation which possessed distorted square-pyramidal geometries. The coordinated acetonitrile N-donor atom occupied the apical position. The analsis showed that the pairs of cations linked by N-H···F hydrogen bonds.
Baum, Gerhard,Blake, Alexander J.,Fenske, Dieter,Hubberstey, Peter,Julio, Carine,Withersby, Matthew A.
p. m542-m544
(2002)
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Nitrate- and nitrite-ligated 3,6-bis(imidazolyl)pyridazine-bridged dinuclear copper(II) cations with copper-copper separations similar to that in Achromobacter cycloclastes nitrite reductase
The 4,4′-bipyridine (4,4′-bipy) and 3,6-bis(imidazolyl)pyridazine (bimpydz) bridged dinuclear copper(II)-diethylenetriamine (dien) complexes, [{Cu(dien)}2(μ-diimine)][NO3] 4·xH2O (diimine = 4,4-bipy, x = 21; diimine = bimpydz, x = 05), [{Cu(dien)}2(μ-diimine)][BF4]4·4MeCN (diimine = 4,4-bipy 2 or bimpydz 6) and [{Cu(dien)}2(μ-bimpydz)]Cl4·4H2O 4, have been synthesised and characterised. Reaction of the tetrafluoroborates, 2 and 6, with NaNO2 yields the nitrites [{Cu(dien)}2(μ-diimine)][NO2][BF4] 3·xMeCN (diimine = 4,4-bipy, x = 03; diimine = bimpydz, x = 0.57). Neither the chloride nor the nitrates react with NaNO2. Structural analysis of complexes 5 and 7 has shown that although they are both based on the dinuclear cationic unit, [{Cu(dien)}2(μ-bimpydz)]4+, in 5 the bimpydz bridge adopts a transoid arrangement of imidazole molecules, whereas in 7 it adopts a cisoid arrangement, giving Cu ... Cu separations of 13.28 and 12.88 A, respectively. In 5, the dications are linked by two axially co-ordinated nitrate anions, one strongly bound, the other very weakly bound, to give chains with a ladder-type motif. In 7, the dications are bridged by μ-nitrito-κO:κN moieties to form a chain with helical geometry. The copper(II)-nitrite interaction is novel; the anion bridges the weakly binding axial positions of two square-pyramidal copper atoms using the nitrogen lone pair and the syn lone pair of an oxygen.
Begley, Michael J.,Hubberstey, Peter,Stroud, Jo
p. 4295 - 4301
(1996)
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Correction to: Nickel-catalyzed enantioselective reductive cross-coupling of styrenyl aziridines (Journal of the American Chemical Society (2017) 139 (5688-5691) DOI: 10.1021/jacs.7b03448)
Table of Contents. The enantiomer of the BiOx ligand that delivers the indicated absolute configuration of product is (R,R)-(4-heptyl)BiOx. The corrected graphic is shown below: Page 5690. The absolute configuration of ligand L7 (4-heptyl- BiOx) was misas
Woods, Brian P.,Orlandi, Manuel,Huang, Chung-Yang Dennis,Sigman, Matthew S.,Doyle, Abigail G.
supporting information
p. 7744 - 7745
(2018/06/26)

Copper-Catalyzed C-N Bond Exchange of N-Heterocyclic Substituents around Pyridine and Pyrimidine Cores
A copper-catalyzed transfer N-heteroarylation strategy using a C-N bond exchange reaction is described. This reaction accommodates a wide range of pyridine and pyrimidine rings bearing halogen atoms, which have wide utility for subsequent transformations. This method provides a direct and operationally simple approach for modifying complex molecules by the exchange of N-heterocyclic substituents.
Tao, Sheng,Ji, Enhui,Shi, Lei,Liu, Ning,Xu, Liang,Dai, Bin
p. 5120 - 5130
(2017/11/28)

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines
A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows
Woods, Brian P.,Orlandi, Manuel,Huang, Chung-Yang,Sigman, Matthew S.,Doyle, Abigail G.
supporting information
p. 5688 - 5691
(2017/05/04)

CuII-catalyzed regioselective borylation of alkynes and alkenes
We developed a regioselective borylation of alkynes and alkenes protocol based on air-stable CuII/multi-dentate ligand system. Our catalytic system gives exclusive β-borylation products for most substrates in excellent chemical yields. We propo
Liu, Shiwen,Zeng, Xiaojun,Xu, Bo
supporting information
p. 3706 - 3710
(2016/07/26)

The non-innocent nature of graphene oxide as a theranostic platform for biomedical applications and its reactivity towards metal-based anticancer drugs
The self-assembly process in a solution of a mononuclear iron(ii) complex based on the bispyrazolylpyridine scaffold with graphene oxide (GO) micrometer-sheets allows not only the devising of a new hybrid-architecture for GO-based materials suitable for nanomedicine, but also the unveiling of the reactive nature of GO as a drug-carrier. The neat iron complex is found to be highly active in disrupting the cell cycle through DNA binding, with behaviour and efficiency similar to that expressed by ruthenium-complexes as well as antibiotic-drugs such as doxorubicin. On the contrary, in the hybrid material the proclivity of neat GO to produce reactive oxygen species (ROS) became down-regulated by the electron-buffering properties of the loaded iron complex, evidencing the presence of an active electron transfer from the drug to GO. These findings question the use of the neat GO platform as a suitable carrier for metal-based anticancer drugs and highlight the importance of addressing the chemical/physical integrity of the drug being loaded into GO before drawing conclusions on the potential effectiveness of the hybrid material for medical applications.
Mokdad, Audrey,Dimos, Konstantinos,Zoppellaro, Giorgio,Tucek, Jiri,Perman, Jason A.,Malina, Ondrej,Andersson, K. Kristoffer,Ramanatha Datta, Kasibhatta Kumara,Froning, Jens Peter,Zboril, Radek
p. 76556 - 76566
(2015/09/22)

Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides
A new substrate class for nickel-catalyzed C(sp3) cross-coupling reactions is reported. α-Oxy radicals generated from benzylic acetals, TMSCl, and a mild reductant can participate in chemoselective cross-coupling with aryl iodides using a 2,6-bis(N-pyrazolyl)pyridine (bpp)/Ni catalyst. The mild, base-free conditions are tolerant of a variety of functional groups on both partners, thus representing an attractive C-C bond-forming approach to dialkyl ether synthesis. Characterization of a [(bpp)NiCl] complex relevant to the proposed catalytic cycle is also described.
Arendt, Kevin M.,Doyle, Abigail G.
supporting information
p. 9876 - 9880
(2015/08/19)

DOPANTS FOR SOLID-STATE DYE-SENSITIVE SOLAR CELLS
The present invention provides a new complex of formula (I) that is useful as p-dopant. The new complex is a complex of Co3+, Ni3+, Cr3+, Mn3+or Fe3+, and contains new be- or- tridentate ligands. The invention also relates to the use of the new complex as p-dopant in hole-transporting-material (HTM). The invention further relates to HTM p-doped with the complex of the invention. The invention further relates to photo-electrochemical device such as solar cell, in particular solid state dye sensitized solar cells (ssDSCs) that comprise the complex of the invention.
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Paragraph 0077

(2014/06/11)

Synthesis, characterization, and butadiene polymerization of iron(III), iron(II) and cobalt(II) chlorides bearing 2,6-bis(2-benzimidazolyl)pyridyl or 2,6-bis(pyrazol)pyridine ligand
Iron(III), iron(II) and cobalt(II) complexes bearing neutral N,N,N-tridentate ligand (Fe(III)L1, 1a; Fe(III)L2, 1b; Fe(III)L3, 1c; Fe(III)L4, 2a; Fe(III)L5, 2b; Fe(III)L6, 2c; Fe(II)L1, 3a; Fe(II)L2, 3b; Fe(II)L3, 3c; Fe(II)L4, 4a; Fe(II)L5, 4b; Fe(II)L6, 4c; CoL1, 5a; CoL2, 5b; CoL3, 5c; CoL5, 6b and CoL6, 6c) have been synthesized from the metal chlorides (FeCl3, FeCl2·4H2O or CoCl2) by treating the corresponding ligands (2,6-bis(benzimidazol-2-yl)pyridine, L1; 2,6-bis(1′-ethylbenzimidazol-2′-yl)pyridine, L2; 2,6-bis(1′-benzylbenzimidazol-2′-yl)pyridine, L3; 2,6-bis(pyrazol)pyridine L4; 2,6-bis(3-methylpyrazol)pyridine, L5 or 2,6-bis(3,5-dimethylpyrazol)pyridine, L6. The complexes are characterized by FTIR and elemental analyses. The structures of complexes 1a, 1b, 3a, 3b, 3c, 4a, 5a, 5b, 5c and 6c are further confirmed by X-ray crystallographic analyses. Six coordination iron(III) (1a, 1b and 1c) and iron(II) (3c*DMF) complexes adopt a distorted octahedral configuration with the equatorial plane formed by the three nitrogen atoms and one chlorine atom, while the iron(II) (3a, 3b and 4a) and cobalt complexes (5a, 5b, 5c and 6c) adopt a trigonal bipyramidal configuration with the equatorial plane formed by the pyridyl nitrogen atoms and the two chlorine atoms. All complexes are evaluated as precursors for 1,3-butadiene polymerization in the presence of cocatalyst in toluene at room temperature. Iron(III) and iron(II) bearing the same ligand show comparable catalytic performance. The catalytic activity and selectivity are significantly influenced by the ligand structure, with the latter being tunable within a wide range from cis-1,4 to trans-1,4. Cobalt complexes, in combination with either MAO or aluminum chlorides shown high activity, and high cis-1,4-selectivity irrespective of the structure of ligand backbone.
Gong, Dirong,Jia, Xiaoyu,Wang, Baolin,Zhang, Xuequan,Jiang, Liansheng
scheme or table
p. 10 - 18
(2012/03/12)

Unexpected product distributions in the synthesis of 2,6-bis-(indazolyl)pyridine and 2-(pyrazol-1-yl)-6-(indazolyl)pyridine
Reaction of 2-bromopyridine with 2 equiv of sodium indazolide in diglyme at 140 °C affords 2,6-bis-(indazol-1-yl)pyridine and 2-(indazol-1-yl)-6-(indazol-2-yl)pyridine in purified yields of 24% and 68% respectively. A similar reaction, using 1 equiv of so
Pritchard, Ruth,Kilner, Colin A.,Halcrow, Malcolm A.
supporting information; experimental part
p. 2484 - 2486
(2009/08/17)

POLYCYCLIC PYRIDINES AS POTASSIUM ION CHANNEL MODULATORS
The present invention provides a genus of polycyclic pyridines that are useful as modulators of potassium ion channels. The modulators of the invention are of use in both therapeutic and diagnostic methods.
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Page/Page column 77-78

(2010/02/14)

2,6-Bis(N-pyrazolyl)pyridines: The Convenient Synthesis of a Family of Planar Tridentate N3 Ligands That Are Terpyridine Analogues
A series of four symmetric 2,6-bis(N-pyrazolyl)pyridines were prepared in good yields by the reaction of an excess of potassium pyrazolate with 2,6-dihalopyridines in the solvent diglyme.Pyrazoles bearing bulky substituents react at the less sterically hi
Jameson, Donald L.,Goldsby, Kenneth A.
p. 4992 - 4994
(2007/10/02)