III.—On chloranil and bromanil. No. II

Stenhouse, John

doi:10.1039/js8702300006

Cited by 5 publications

(7 citation statements)

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“…H 4 ClCNan was prepared by a similar procedure from K 2 ClCNan⋅H 2 O, which was prepared by the procedure of Atzori et al . H 4 Bran was prepared from H 2 Bran by a similar procedure, which was prepared by the procedure of Stenhouse …”

Section: Methodsmentioning

confidence: 99%

“…[24] H 4 ClCNan was prepared by as imilar procedure from K 2 ClCNan·H 2 O, which was prepared by the procedure of Atzori et al [5f] H 4 Bran was prepared from H 2 Bran by as imilar procedure, which was prepared by the procedure of Stenhouse. [25] (Et 4 N)[Y(can) 2 ]·(CH 3 ) 2 CO:Asolution of H 4 can (1.0 mmol, 0.21 g) and LiOAc (2.0 mmol, 0.13 g) in acetone (20 mL) was layered above Y III (NO 3 ) 3 ·6 H 2 O( 0.50 mmol, 0.19 g) and Et 4 NBr (2.0 mmol, 0.42 g) in water (10 mL). This solution was left to stand in ap artially covered flask and crystals appeared at the interface between the two solutions within two days.…”

Section: Methodsmentioning

confidence: 99%

“…Site occupancy trends obtained Chem.E ur.J. 2019,25,[5222][5223][5224][5225][5226][5227][5228][5229][5230][5231][5232][5233][5234] www.chemeurj.org by refinement againstt he isothermal NPD data series also agreed well with the findings of the high-resolution study, except that the filling of site 3c ommenceda tt he lowest loadings and increased continuouslyo ver the whole D 2 concentration range (Figure 9). We speculate that at the slightly higher temperatures used duringt he isothermal NPD experiment, the D 2 molecules are able to move between the closely neighbouring sites 1a nd 3, leading to co-filling of both of these sites until the increased concentration renders the low-capacity site 1u nfavourable.…”

Section: Comentioning

confidence: 99%

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Square Grid Metal–Chloranilate Networks as Robust Host Systems for Guest Sorption

Kingsbury

Abrahams

Auckett

et al. 2019

Chemistry A European J

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Reaction of the chloranilate dianion with Y(NO3)3 in the presence of Et4N+ in the appropriate proportions results in the formation of (Et4N)[Y(can)2], which consists of anionic square‐grid coordination polymer sheets with interleaved layers of counter‐cations. These counter‐cations, which serve as squat pillars between [Y(can)2] sheets, lead to alignment of the square grid sheets and the subsequent generation of square channels running perpendicular to the sheets. The crystals are found to be porous and retain crystallinity following cycles of adsorption and desorption. This compound exhibits a high affinity for volatile guest molecules, which could be identified within the framework by crystallographic methods. In situ neutron powder diffraction indicates a size‐shape complementarity leading to a strong interaction between host and guest for CO2 and CH4. Single‐crystal X‐ray diffraction experiments indicate significant interactions between the host framework and discrete I2 or Br2 molecules. A series of isostructural compounds (cat)[MIII(X‐an)2] with M=Sc, Gd, Tb, Dy, Ho, Er, Yb, Lu, Bi or In, cat=Et4N, Me4N and X‐an=chloranilate, bromanilate or cyanochloranilate bridging ligands have been generated. The magnetic properties of representative examples (Et4N)[Gd(can)2] and (Et4N)[Dy(can)2] are reported with normal DC susceptibility but unusual AC susceptibility data noted for (Et4N)[Gd(can)2].

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Comentioning

confidence: 99%

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Square Grid Metal–Chloranilate Networks as Robust Host Systems for Guest Sorption

Kingsbury

Abrahams

Auckett

et al. 2019

Chemistry A European J

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“…A simple change of one chloro substituent on the chloranilate ligand with a cyano group affects the electronic properties of the anilate moiety inducing unprecedented luminescence properties in the class of anilate-based ligands and their metal complexes. The synthesis and full characterization, including photoluminescence studies, of the chlorocyananilate ligand (ClCNAn 2− ), a unique example of a heterosubstituted anilate ligand has been recently reported [120], along with the tris-chelated metal complexes with Cr(III), (10) Fe(III), (11) and Al(III) (12) The crystal structures of the M(III) chlorocyananilate complexes consist of homoleptic tris-chelated complex anions of formula [M(ClCNAn) 3 ] 3− (M = Cr(III), Fe(III), Al(III)), exhibiting octahedral geometry and [(n-Bu) 4 N] + or [Ph 4 P] + cations. The 10a-12a complexes are isostructural and their crystal packing is characterized by the presence of C-N· · · Cl interactions between complex anions having an opposite stereochemical configuration (Λ, ∆), responsible for the formation of infinite 1D supramolecular chains parallel to the a crystallographic axis ( Figure 6).…”

Section: Molecular Paramagnetsmentioning

confidence: 99%

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

et al. 2017

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Abstract:The aim of the present work is to highlight the unique role of anilato-ligands, derivatives of the 2,5-dioxy-1,4-benzoquinone framework containing various substituents at the 3 and 6 positions (X = H, Cl, Br, I, CN, etc.), in engineering a great variety of new materials showing peculiar magnetic and/or conducting properties. Homoleptic anilato-based molecular building blocks and related materials will be discussed. Selected examples of such materials, spanning from graphene-related layered magnetic materials to intercalated supramolecular arrays, ferromagnetic 3D monometallic lanthanoid assemblies, multifunctional materials with coexistence of magnetic/conducting properties and/or chirality and multifunctional metal-organic frameworks (MOFs) will be discussed herein. The influence of (i) the electronic nature of the X substituents and (ii) intermolecular interactions i.e., H-Bonding, Halogen-Bonding, π-π stacking and dipolar interactions, on the physical properties of the resulting material will be also highlighted. A combined structural/physical properties analysis will be reported to provide an effective tool for designing novel anilate-based supramolecular architectures showing improved and/or novel physical properties. The role of the molecular approach in this context is pointed out as well, since it enables the chemical design of the molecular building blocks being suitable for self-assembly to form supramolecular structures with the desired interactions and physical properties.Keywords: benzoquinone derivatives; molecular magnetism; multifunctional molecular materials; spin-crossover materials; metal-organic frameworks General IntroductionThe aim of the present work is to highlight the key role of anilates in engineering new materials with new or improved magnetic and/or conducting properties and new technological applications. Only homoleptic anilato-based molecular building blocks and related materials will be discussed. Selected examples of para-/ferri-/ferro-magnetic, spin-crossover and conducting/magnetic multifunctional materials and MOFs based on transition metal complexes of anilato-derivatives, on varying the substituents at the 3,6 positions of the anilato moiety, will be discussed herein, whose structural features or physical properties are peculiar and/or unusual with respect to analogous compounds reported in the literature up to now. Their most appealing technological applications will be also reported.

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“…Bromanil (1) was synthesized according to the literature. 23 2-(Tributylstannyl)thiophene was purchased from Sigma-Aldrich and 2-(tributylstannyl)-3,4-ethylenedioxythiophene was synthesized according to the literature. 24 [Cu(tbbpy)Cl 2 ] (tbbpy = 4,4′-bis(tert-butyl)-2,2′-bipyridine) was synthesized according to the literature method.…”

Section: Methodsmentioning

confidence: 99%

Thiophene-benzoquinones: synthesis, crystal structures and preliminary coordination chemistry of derived anilate ligands

et al. 2014

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2,5-Bis(thiophene) and 2,5-bis(ethylenedioxy-thiophene) (EDOT) derivatives of 3,6-diethoxy-1,4-benzoquinone (para isomers) were prepared by Stille coupling between the 2,5-dibromo-3,6-diethoxy-1,4-benzoquinone precursors and (n-Bu)3Sn-R (R = 2-thiophenyl or 3,4-ethylenedioxy-2-thiophenyl) reagents. In a parallel series of experiments 2,6-bis(thiophene) and 2,6-EDOT-3,5-diethoxy-1,4-benzoquinone (meta isomers) were synthesized by the same strategy. The four compounds were structurally characterized. The thiophene derivatives show essentially planar conformation thanks to the conjugation and establishment of S···O 1,5-nonbonded interactions, while in the EDOT derivatives the thiophene moieties are twisted with respect to the benzoquinone ring because of the steric hindrance. TD-DFT calculations were performed on both para and meta thiophene isomers in order to explain the differences observed in the UV-Vis absorption spectra. The 2,5-derivatives are valuable precursors for thiophene containing anilate (An) ligands, as the first examples of electron rich substituent based anilates. The Cu(II) complex [Cu(Th2An)(tbbpy)]·2H2O (Th2An = thiophene-anilate; tbbpy = 4,4'-bis(tert-butyl)-2,2'-bipyridine) was isolated and structurally characterized. The metal center lies within a square planar coordination geometry, while the ligands engage in a set of intermolecular contacts.

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III.—On chloranil and bromanil. No. II

Cited by 5 publications

References 0 publications

Square Grid Metal–Chloranilate Networks as Robust Host Systems for Guest Sorption

Square Grid Metal–Chloranilate Networks as Robust Host Systems for Guest Sorption

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

Thiophene-benzoquinones: synthesis, crystal structures and preliminary coordination chemistry of derived anilate ligands

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