m-phosphonobenzoic acid and copper(II) as precursors of helical chain and lamellar hybrid materials

Rueff, Jean‐Michel; Caignaert, V.; Leclaire, A.; Simon, Charles; Haelters, Jean‐Pierre; Jaffrès, Paul‐Alain

doi:10.1039/b816132c

Cited by 38 publications

(46 citation statements)

References 27 publications

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“…18 Reaction of the carboxylic−phosphonic derivative B with copper salts gives rise to a homochiral helical structure. 19 The same organic precursor B reacted with zinc nitrate has produced a 2D or 3D hybrid material depending on the pH of the reaction media, illustrating the possibility with some experimental conditions to observe chemoselectivity in the course of hybrid material construction. 20 Finally, compound C when combined with a copper salt produced a complex 3D structure 21 made of inorganic columns connected by organic parts.…”

Section: ■ Introductionmentioning

confidence: 98%

Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn₂(O₃P–C₄H₂S–PO₃)·2H₂O

et al. 2012

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Synthesis of thiophene-2,5-diphosphonic acid 2 is reported, and its use for synthesis of the original pristine materials Mn(2)(O(3)P-C(4)H(2)S-PO(3))·2H(2)O 3 is reported. The structure of material 3 has been fully resolved from single-crystal X-ray diffraction. Mn(2)(O(3)P-C(4)H(2)S-PO(3))·2H(2)O 3 crystallizes in a monoclinic cell (space group P2) with the following parameters: a = 11.60(1) Å, b = 4.943(5) Å, c = 19.614(13) Å, β = 107.22°. A noticeable feature of the structure of compound 3 is the orientation of the thiophene heterocycles that adopt two different orientations in two successive layers (along c). Thermal analysis of compound 3 indicates that the water molecules are easily removed from 160 to 230 °C while the dehydrated structure is stable up to 500 °C. The dehydrated compound obtained from 3 can be rehydrated to give the polymorphic compound Mn(2)(O(3)P-C(4)H(2)S-PO(3))·2H(2)O 4, which crystallizes in an orthorhombic cell (space group Pnam) with the following parameters: a = 7.5359(3) Å, b = 7.5524(3) Å, c = 18.3050(9) Å. The main difference between the structures of 3 and 4 arises from both the orientation of the thiophene rings (herringbone-type organization in 4) and the structure of the inorganic layers. The thiophene-2,5-diphosphonic acid moieties engaged in materials 3 and 4 adopt a different orientation likely due to rotation around the P-C bonds and via the dehydrated state 5, which is likely more flexible than the hydrated states. Study of the magnetic properties performed on compound 3 and 4 and on the dehydrated compounds Mn(2)(O(3)P-C(4)H(2)S-PO(3)) 5 complemented by the structural study has permitted us to characterize the antiferromagnetic ground state of sample 3, a weak ferromagnetic component in sample 4, and complete paramagnetic behavior in sample 5.

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Section: ■ Introductionmentioning

confidence: 98%

Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn₂(O₃P–C₄H₂S–PO₃)·2H₂O

et al. 2012

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“…32 This work was carried out within a context that aimed to study that aimed to examine the use of rigid phosphonic acid derivatives 33 , 34 as building blocks for the construction of crystalline hybrids under hydrothermal conditions to produce fluorescent, 35 thermally stable 36 and non-centrosymmetic materials. 37,38 For Through the study of the construction synthesis of silver-based hybrids we produced materials were produced with which couldthe potentially of acting as a reservoir of silver ions i.e. theyat could, via a disassembling of the hybrid in an aqueous media, exhibit bactericidal properties.…”

Section: Introductionmentioning

confidence: 99%

Silver-Based Hybrid Materials from meta- or para-Phosphonobenzoic Acid: Influence of the Topology on Silver Release in Water

et al. 2015

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(Word Style "BD_Abstract").Three novel silver-based Metal Organic Frameworks materials which were synthesized from either 3-phosphono or 4-phosphonobenzoic acid and silver nitrate are reported. The novel hybrids were synthesized under hydrothermal conditions; the pH of the reaction media was controlled by adding different quantities of urea thereby producing different topologies.Compound 1 (Ag3(4-PO3-C6H4-COO)), synthesised in presence of urea, exhibits a compact 3D structure in which both phosphonic acid and carboxylic acid functional groups are linked to the silver-based inorganic network. Compound 2 (Ag(4-PO3H-C6H4-COOH)), which was synthesized at lower pH (without urea), has a layered structure in which only the phosphonic acid functional groups from 4-phosphonobenzoic acid moieties are linked to the silver inorganic network; the carboxylic acid groups being engaged in hydrogen bonds. Finally, material 3 (Ag(3-PO3H-C6H4-COOH)) was synthesised from 3-phosphonobenzoic acid and silver nitrate without urea. This material 3 features a layered structure exhibiting carboxylic acid functional groups linked via hydrogen bonds in the interlayer space. After the full characterization of these materials (single X-ray structure, IR, TGA), their ability to release silver salts in aqueous environment was measured. Silver release, determined in aqueous solution by cathodic stripping voltammetry, shows that the silver release capacity of these materials is dependent on the topology of the hybrids. The more compact structure 1 is extremely stable in water with only trace levels of silver ions being detected. On the other hand, compounds 2 and 3, in which only the phosphonic acid functional groups were bonded to the inorganic network, released larger quantities of silver ions into aqueous solution. These results which were compared with the silver release of the previously described compound 4 (Ag6(3-PO3-C6H4-COO)2). The results clearly show that the release capacity of silver-based metal organic framework can be tuned by 3 modifying their topology which, in the present study, is governed by the regio-isomer of the organic precursor and the synthetic conditions under which the hybrids are prepared.4

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“…It is worth noting that the same organic building block associated with another metallic source (Cu) produces a homochiral helical structure. [23] These results clearly show that the final structure of the hybrid is imposed by both the rigidity of the organic building block and the nature of the inorganic source.…”

Section: Introductionmentioning

confidence: 87%

Lead(II) Hybrid Materials from 3‐ or 4‐Phosphonobenzoic Acid

et al. 2009

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International audienceThree new hybrid organic-inorganic materials Pb3(H2O)2(p-PO3C6H4CO2)2 (2), Pb6(H2O)2(p-PO3C6H4CO2)4 (3), and Pb5(p-PO3C6H4COOH)2(p-PO3C6H4CO2)2 (4) have been synthesized by hydrothermal treatment involving PbII salts and a rigid heterodifunctional precursor 4-phosphonobenzoic acid {p-PO(OH)2C6H4COOH}. The use of 3-phosphonobenzoic acid {m-PO(OH)2C6H4COOH} as another rigid organic precursor is also reported. These two organic building units possess two distinct functional groups (phosphonic acid and carboxylic acid) both having the aptitude to generate chemical bonds with a metallic precursor. The structures of the produced materials have been solved by means of single-crystal X-ray diffraction data. It was observed that the use of the 4-phosphonobenzoic acid produces the hybrids 2, 3, or 4 that possess a layered structure. In these three materials, the inorganic planes are linked together via an organic bridge. For 2, 3 and 4 the understanding of the stacking of the organic molecules within the layer, the influence of the electronic lone pair and the water molecules is discussed.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009

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m-phosphonobenzoic acid and copper(II) as precursors of helical chain and lamellar hybrid materials

Cited by 38 publications

References 27 publications

Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn₂(O₃P–C₄H₂S–PO₃)·2H₂O

Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn₂(O₃P–C₄H₂S–PO₃)·2H₂O

Silver-Based Hybrid Materials from meta- or para-Phosphonobenzoic Acid: Influence of the Topology on Silver Release in Water

Lead(II) Hybrid Materials from 3‐ or 4‐Phosphonobenzoic Acid

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m-phosphonobenzoic acid and copper(II) as precursors of helical chain and lamellar hybrid materials

Cited by 38 publications

References 27 publications

Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn2(O3P–C4H2S–PO3)·2H2O

Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn2(O3P–C4H2S–PO3)·2H2O

Silver-Based Hybrid Materials from meta- or para-Phosphonobenzoic Acid: Influence of the Topology on Silver Release in Water

Lead(II) Hybrid Materials from 3‐ or 4‐Phosphonobenzoic Acid

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Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn₂(O₃P–C₄H₂S–PO₃)·2H₂O

Structural Study of Hydrated/Dehydrated Manganese Thiophene-2,5-diphosphonate Metal Organic Frameworks, Mn₂(O₃P–C₄H₂S–PO₃)·2H₂O