Synthesis, crystal structures, and luminescent properties of Pb(II) and Sr(II) coordination polymers constructed by 5-methyl-1H-pyrazole-3-carboxylic acid

Cheng, Mei-Ling; Han, Wei; Liu, Qi; Bao, Jinting; Li, Zhanfeng; Chen, Lin-Ti; Sun, Xiaoqiang; Xi, Huan

doi:10.1080/00958972.2013.879983

Cited by 24 publications

(2 citation statements)

References 38 publications

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“…Pyrazole is a five-membered aromatic heterocycle with two adjacent nitrogen atoms, classified as azole. Pyrazole derivatives have broad application, from engineering and polymers [1,2,3,4,5,6,7,8], to biological activity [9]; thus, new synthetic strategies are constantly developed [10,11,12,13,14,15,16,17]. Among them, there are 1 H -pyrazoles with substituents at positions 3 and 5, which reveal interesting applications [18,19,20,21,22,23,24,25], and some of them are depicted in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Annular Tautomerism of 3(5)-Disubstituted-1H-pyrazoles with Ester and Amide Groups

et al. 2019

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A series of disubstituted 1H-pyrazoles with methyl (1), amino (2), and nitro (3) groups, as well as ester (a) or amide (b) groups in positions 3 and 5 was synthesized, and annular tautomerism was investigated using X-ray, theoretical calculations, NMR, and FT-IR methods. The X-ray experiment in the crystal state showed for the compounds with methyl (1a, 1b) and amino (2b) groups the tautomer with ester or amide groups at position 3 (tautomer 3), but for those with a nitro group (3b, 4), tautomer 5. Similar results were obtained in solution by NMR NOE experiments in CDCl3, DMSO-d6, and CD3OD solvents. However, tautomer equilibrium was observed for 2b in DMSO. The FT-IR spectra in chloroform and acetonitrile showed equilibria, which can be ascribed to conformational changes of the cis/trans arrangement of the ester/amide group and pyrazole ring. Theoretical analysis using the M06-2X/6-311++G(d,p) method (in vacuo, chloroform, acetonitrile, and water) and measurement of aromaticity (NICS) showed dependence on internal hydrogen bonds, the influence of the environment, and the effect of the substituent. These factors, pyrazole aromaticity and intra- and inter-molecular interactions, seem to have a considerable influence on the choice of tautomer.

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Section: Introductionmentioning

confidence: 99%

Annular Tautomerism of 3(5)-Disubstituted-1H-pyrazoles with Ester and Amide Groups

et al. 2019

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“…Many CPs with functional properties based on 3,4-pyrazoledicarboxylic acid, 3,5-dimethyl-1 H -pyrazole-4-carboxylic acid, 1 H -pyrazole-4-carboxylic acid, 5-methyl-1 H -pyrazole-3-carboxylic acid, 1-carboxymethyl-3,5-dimethyl-1 H -pyrazole-4-carboxylic acid, etc. have been synthesized by us and other research groups. − However, to the best of our knowledge, only a few CPs derived from 3-methyl-1 H -pyrazole-4-carboxylic acid (H 2 mpca) have been reported by us so far. , Tetrafluoroterephthalic acid (H 2 tfbdc), as a versatile linker similar to 1,4-benzenedicarboxylic acid, has been used in synthesizing CPs with interesting structures and properties. − For instance, two-dimensional (2D) CPs Ln(tfbdc) 1.5 ·DMF·H 2 O (Ln = Pr 3+ ( 1 ), Nd 3+ ( 2 )) present antiferromagnetic property; [Mn(tfbdc)(4,4′-bpy)(H 2 O) 2 ], a 2D CP, serves as an anode material for Li-ion batteries, displaying a reversible specific capacity of 390 mA h g –1 . However, three-dimensional (3D) CPs based on H 2 tfbdc and H 2 mpca ligands have not been reported so far.…”

Section: Introductionmentioning

confidence: 99%

A Three-Dimensional Copper Coordination Polymer Constructed by 3-Methyl-1H-pyrazole-4-carboxylic Acid with Higher Capacitance for Supercapacitors

Wang

Cheng

et al. 2017

Crystal Growth & Design

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A three-dimensional (3D) copper-based coordination polymer, ([Cu(H 2 mpca)-(tfbdc)], Cu-CP; H 2 mpca = 3-methyl-1H-pyrazole-4-carboxylic acid; H 2 tfbdc = 2,3,5,6tetrafluoroterephthalic acid), has been synthesized and characterized by IR spectroscopy, thermogravimetric analysis, elemental analysis, and single-crystal X-ray diffraction. In Cu-CP, each Cu(II) ion is located in a triangular bipyramid geometry, and these Cu(II) ions are linked by tfbdc 2− ligands to produce a 3D network. Variable-temperature magnetic susceptibility data display that weak antiferromagnetic interactions between the adjacent Cu (II) ions exist in Cu-CP. Cu-CP was evaluated as an electrode material for supercapacitors. It displayed a higher specific capacitance of 735 F g −1 in 1 M KOH solution at a current density of 1 A g −1 and remained at 375 F g −1 after 1500 cycles at 2 A g −1 .

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Synthesis and Structural Diversity of Main Group Metal Coordination Complexes Constructed from V‐Shape Bis(3‐methyl‐1H‐pyrazole‐4‐carboxylic acid)alkane Ligands

Cheng¹,

Bao²,

Wu³

et al. 2018

ChemistrySelect

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Reaction of H2L1/H2L2/H2L3 with corresponding main group metal salts generated five complexes, [Mg(L1)(phen)(H2O)3]⋅5H2O (1, mononuclear), [Sr(CH3OH)(L1)2Sr(H2O)2]2n⋅nH2O (2, 2D), [Ba(L2)(H2O)3]n (3, 2D), [Pb(L2)(2,2′‐bpy)]2n⋅9nH2O (4, 1D) and [Pb(L3)(phen)]2⋅2DMF (5, dinuclear) (H2L1=1,1'‐methylenebis(5‐methyl‐pyrazole‐4‐carboxylic acid, H2L2 = 2'‐methylenebis(3‐methyl‐pyrazole‐4‐carboxylic acid, H2L3=1,1'‐methylenebis(3‐methyl‐pyrazole‐4‐carboxylic acid; 2,2’‐bpy=2,2′‐bpyridine and phen=1,10‐phenanthroline). In the zwitterionic complex 1, a loop‐loop water‐water hydrogen bonded chain presented in the 3D supramolecular network, which was constructed by π⋅⋅⋅π interactions and hydrogen bonds. In CPs 2 and 3, the 1D inorganic M–O–M connectivity was built from Sr2O16 and BaO9 polyhedra, respectively. The similar 24‐membered Pb2(L2)2/Pb2(L3)2 macrocycle occurred in both 1D polymer 4 and dinuclear complex 5, with two 2,2’‐bpy molecules located inside or two phen molecules outside each macrocycle respectively. The thermal and photoluminescent properties of 1–5 in the solid state have also been investigated.

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Synthesis, crystal structures, and luminescent properties of Pb(II) and Sr(II) coordination polymers constructed by 5-methyl-1H-pyrazole-3-carboxylic acid

Cited by 24 publications

References 38 publications

Annular Tautomerism of 3(5)-Disubstituted-1H-pyrazoles with Ester and Amide Groups

Annular Tautomerism of 3(5)-Disubstituted-1H-pyrazoles with Ester and Amide Groups

A Three-Dimensional Copper Coordination Polymer Constructed by 3-Methyl-1H-pyrazole-4-carboxylic Acid with Higher Capacitance for Supercapacitors

Synthesis and Structural Diversity of Main Group Metal Coordination Complexes Constructed from V‐Shape Bis(3‐methyl‐1H‐pyrazole‐4‐carboxylic acid)alkane Ligands

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