The coordination chemistry of N-heterocyclic carboxylic acid: A comparison of the coordination polymers constructed by 4,5-imidazoledicarboxylic acid and 1H-1,2,3-triazole-4,5-dicarboxylic acid

Zhang, Shaowei; Shi, Wei

doi:10.1016/j.ccr.2017.08.022

Cited by 111 publications

(34 citation statements)

References 192 publications

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“…In fact, CPs 1 and 2 represent unique examples of metal-containing derivatives constructed from H 4 deta. This work thus extends a variety of multifunctional carboxylic acids applied in the synthesis of coordination polymers [44][45][46][47][48][49][50].…”

Section: Discussionmentioning

confidence: 73%

A Flexible Aromatic Tetracarboxylate as a New Linker for Coordination Polymers

Kirillov

2020

Crystals

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Two new cadmium(II)-based materials, featuring two-dimensional (2D) [Cd2(μ6-deta)(bpy)(H2O)]n (1) and three-dimensional (3D) [Cd2(μ5-deta)(bpy)2(H2O)]n (2) structures, were constructed by the hydrothermal method from 2,3′,4′,5-diphenyl ether tetracarboxylic acid (H4deta) as an unexplored linker in research on coordination polymers (CPs) and 2,2′-bipyridine (bpy) as a mediator of crystallization. Microcrystalline samples of 1 and 2 were analyzed by IR/PXRD/EA/TGA and X-ray diffraction using single crystals. Structures and topologies of CPs 1 and 2 were established, revealing a 4,6L45 topological layer in 1 and a 3,5T1 topological framework in 2. Structural differences for 1 and 2 are attributed to distinct molar ratios between Cd2+ and bpy during the hydrothermal synthesis. Luminescence and thermal behavior of the obtained materials were also investigated. The present work opens up the use of an unexplored 2,3′,4′,5-diphenyl ether tetracarboxylic acid as a versatile and flexible linker toward the generation of functional coordination polymer materials.

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Section: Discussionmentioning

confidence: 73%

A Flexible Aromatic Tetracarboxylate as a New Linker for Coordination Polymers

Kirillov

2020

Crystals

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“…Interestingly,i nt he crystal structure of the product molecule, the C9ÀN1 distance (1.332(2) ,T able S3) of the imidazole ring is the same as the C9ÀN2 distance on the same imidazole ring (1.332 (2) ), that is, the imidazole ring of H 3 MBIDC may have been be protonated.I nt he literature, severalg roups reported that in imidazole or benzimidazole derivatives, the CÀNb ond length of am onoprotonated imidazole ring could be in the range of 1.32-1.35 . [31][32][33][34] Herein,i ti sarational hypothesis that there was ap rotonated Na tom on the imidazole ring of crystalline H 3 MBIDC.I nt he packingd iagram of crystalline H 3 MBIDC (Figure 2a), one water molecule approaches the N2 atom on the protonated imidazole ring by hydrogen bonding (NÀH···O). This suggested that formationo ft he imidazole ring required the presence of water,a nd might even be accelerated by the presence of water.W hen the amount of Cd II salt was decreasedt o4 0mol %, organicc ompound H 3 MBIDC was obtained as the only product.…”

Section: Resultsmentioning

confidence: 99%

Direct Conversion of Benzothiadiazole to Benzimidazole: New Benzimidazole‐Derived Metal–Organic Frameworks with Adjustable Honeycomb‐Like Cavities

Zhao

Han

et al. 2019

Chemistry A European J

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Up to now, the direct conversion of the thiadiazole ring to other heterocyclic rings has been a very challenging task. Herein, a CdII‐mediated alcohol‐substitution strategy for direct conversion from benzothiadiazole to benzimidazole is reported. Experimental and molecular modeling studies on the role of the chelated metal ion in this in situ alcohol‐substitution reaction revealed that it serves as an all‐rounder that is involved in the insertion of alcohol, activation of the thiadiazole ring by coordinative interaction, and the sulfur‐extrusion process. Interestingly, the insertion of alcohol occurs much earlier than the sulfur‐extrusion process, supported by a water‐mediated proton‐transfer process. This strategy also is suitable for constructing new benzimidazole‐derived MOFs [Cd2(HMBIDC2−)2]⋅4 H2O (Cd‐BID‐MOF‐1, HMBIDC2−=2‐methyl‐1H‐benzimidazole‐4,7‐dicarboxylate) and [Cd2(HPBIDC2−)2]⋅1/3 H2O (Cd‐BID‐MOF‐2, HPBIDC2−=2‐(3‐hydroxypropyl)‐2H‐benzimidazole‐4,7‐dicarboxylate). Because the terminal hydroxyl group on the imidazole ring protrudes into the circular channel in rhombohedral Cd‐BID‐MOF‐2, the cavity is closer to hydrophilic than the honeycomb‐like cavity in Cd‐BID‐MOF‐1 with similar 3D structure. This rare observation will provide a new strategy to develop in situ ligand‐reaction synthesis of functional MOFs and useful chelation‐assisted catalytic reactions in heteroaromatic chemistry.

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“…In investigated in the field of crystal engineering and material science, owning to not only by its intriguing topological structures [3], but also their widely applications in various fields, such as catalysis [4], magnetism [5], luminescence [6], gas selective adsorption [7] and so on. As a typical Nheterocyclic carboxylic acid ligand, PTPBA contains both heterocyclic nitrogen atoms and the carboxylic group and can provide versatile coordination modes.…”

Section: Commentmentioning

confidence: 99%

Crystal structure of dichlorido-bis[2-(2-(3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)phenoxy)benzoic acidmanganese(II) monohydrate, C₄₀H₃₀N₈O₇MnCl₂

Zhang

Luo

et al. 2020

Zeitschrift Für Kristallographie - New Crystal Structures

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The coordination chemistry of N-heterocyclic carboxylic acid: A comparison of the coordination polymers constructed by 4,5-imidazoledicarboxylic acid and 1H-1,2,3-triazole-4,5-dicarboxylic acid

Cited by 111 publications

References 192 publications

A Flexible Aromatic Tetracarboxylate as a New Linker for Coordination Polymers

A Flexible Aromatic Tetracarboxylate as a New Linker for Coordination Polymers

Direct Conversion of Benzothiadiazole to Benzimidazole: New Benzimidazole‐Derived Metal–Organic Frameworks with Adjustable Honeycomb‐Like Cavities

Crystal structure of dichlorido-bis[2-(2-(3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)phenoxy)benzoic acidmanganese(II) monohydrate, C₄₀H₃₀N₈O₇MnCl₂

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The coordination chemistry of N-heterocyclic carboxylic acid: A comparison of the coordination polymers constructed by 4,5-imidazoledicarboxylic acid and 1H-1,2,3-triazole-4,5-dicarboxylic acid

Cited by 111 publications

References 192 publications

A Flexible Aromatic Tetracarboxylate as a New Linker for Coordination Polymers

A Flexible Aromatic Tetracarboxylate as a New Linker for Coordination Polymers

Direct Conversion of Benzothiadiazole to Benzimidazole: New Benzimidazole‐Derived Metal–Organic Frameworks with Adjustable Honeycomb‐Like Cavities

Crystal structure of dichlorido-bis[2-(2-(3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)phenoxy)benzoic acidmanganese(II) monohydrate, C40H30N8O7MnCl2

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Crystal structure of dichlorido-bis[2-(2-(3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)phenoxy)benzoic acidmanganese(II) monohydrate, C₄₀H₃₀N₈O₇MnCl₂