Supramolecular motifs in s-block metal bound sulfonated monoazo dyes

Kennedy, Alan R.; Hughes, Mhairi P.; Monaghan, M.L.; Staunton, Edward; Teat, Simon J.; Smith, W. Ewen

doi:10.1039/b102106k

Cited by 46 publications

(29 citation statements)

References 17 publications

(16 reference statements)

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“…At 1.256 (3) and 1.432 (2) Å , the N N and N2-C7 bond lengths of L1 in (II) are clearly much shorter and longer, respectively, than their equivalents in L2. They fit well with the ranges found for the 4,4 0 isomer and with those found for monosulfonated azo species with no strong electron-donating ring substituents (Soegiarto et al, 2009(Soegiarto et al, , 2010(Soegiarto et al, , 2011Kennedy et al, 2001Kennedy et al, , 2020. The N N bond in (I) is 1.262 (4) Å and is thus outside the ranges of the literature…”

Section: Table 10supporting

confidence: 84%

“…2020). The azo group is the commonest protonation site for the free acid forms of sulfonated azo dyes that do not bear a more basic substituent (Kennedy et al, 2001(Kennedy et al, , 2020. The asymmetric unit of (III) was found to contain an Na centre, a monoanionic L2 ligand with protonation at azo atom N1, two metal-coordinated water ligands and two non-bound water molecules, one of which is disordered ( Fig.…”

Section: Figurementioning

confidence: 99%

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Structures of five salt forms of disulfonated monoazo dyes

et al. 2020

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The structures of five s-block metal salt forms of three disulfonated monoazo dyes are presented. These are poly[di-μ-aqua-diaqua[μ4-3,3′-(diazane-1,2-diyl)bis(benzenesulfonato)]disodium(I)], [Na2(C12H8N2O6S2)(H2O)4] n , (I), catena-poly[[tetraaquacalcium(II)]-μ-3,3′-(diazane-1,2-diyl)bis(benzenesulfonato)], [Ca(C12H8N2O6S2)(H2O)4] n , (II), catena-poly[[[diaquacalcium(II)]-μ-2-(4-amino-3-sulfonatophenyl)-1-(4-sulfonatophenyl)diazenium] dihydrate], {[Na(C12H10N3O6S2)(H2O)2]·2H2O} n , (III), hexaaquamagnesium bis[2-(4-amino-3-sulfonatophenyl)-1-(4-sulfonatophenyl)diazenium] octahydrate, [Mg(H2O)6](C12H10N3O6S2)2·8H2O, (IV), and poly[[{μ2-4-[2-(4-amino-2-methyl-5-methoxyphenyl)diazen-1-yl]benzene-1,3-disulfonato}di-μ-aqua-diaquabarium(II)] dihydrate], {[Ba(C14H13N3O7S2)(H2O)4]·2H2O} n , (V). Compound (III) is that obtained on crystallizing the commercial dyestuff Acid Yellow 9 [74543-21-8]. The Mg species is a solvent-separated ion-pair structure and the others are all coordination polymers with bonds from the metal atoms to sulfonate groups. Compound (I) is a three-dimensional coordination polymer, (V) is a two-dimensional coordination polymer and both (II) and (III) are one-dimensional coordination polymers. The coordination behaviour of the azo ligands and the water ligands, the dimensionality of the coordination polymers and the overall packing motifs of these five structures are contrasted to those of monosulfonate monoazo congers. It is found that (I) and (II) adopt similar structural types to those of monosulfonate species but that the other three structures do not.

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Section: Table 10supporting

confidence: 84%

Section: Figurementioning

confidence: 99%

Structures of five salt forms of disulfonated monoazo dyes

et al. 2020

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“…[1] Ca14 also behaves as would be predicted from reference [1]. It forms a seemingly simple class 2 complex whose structure is somewhat complicated by the presence of both discrete [ 6 ] moieties in the asymmetric unit (Figure 7). [12] The structure of Ba16: Figure 8 shows that the structure of Ba16 is based on dinuclear Ba dimers where two water molecules and two (m 2 , h 2 )-O 3 S units from dye anions act as Bato-Ba bridges.…”

Section: Metal Coordination Networkmentioning

confidence: 61%

“…An obvious omission from previous work1, 4, 6 is the category of ortho‐ sulfonated azo dyes. Despite being common in commercial colorants, these were omitted from discussion in reference 1.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Structure in s‐Block Metal Complexes of Sulfonated Monoazo Dyes: Discrepant Packing and Bonding Behavior of ortho‐Sulfonated Azo Dyes

Kennedy

Andrikopoulos

Arlin

et al. 2009

Chemistry A European J

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The first solid-state structures of ortho-sulfonated monoazo dyestuffs are reported and compared to those of their para- and meta-sulfonated analogues. The structures of the 16 Na, K, Cs, Mg, Ca, Sr, and Ba ortho-sulfonated salts are found to have fewer M-O(3)S bonds than their isomeric equivalents and this in turn means that the metal type is no longer the prime indicator of which structural type will be adopted. M-O(3)S bonds are replaced by M-OH(2), M-HOR and M-pi interactions, apparently for steric reasons. As well as new bonding motifs, the changed dye shape also leads to new packing motifs. The simple organic/inorganic layering ubiquitous to the para- and meta-sulfonated dye salt structures is replaced by variations (organic bilayers, inorganic channels), each of which correlates with a different degree of molecular planarity in the sulfonated azo dye anion.

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“…Another feature is the presence of an OH group ortho to azo in this compound, providing an extra potential hydrogen-bonding or metal complexing site so as to interact intramolecularly with the azo group to provide the possibility of tautomerism to the keto-hydrazone as is found in commercial monoazo dyes. 32 The optimized structure predicts an intramolecular C-HÐ Ð ÐN N hydrogen bonding. The HÐ Ð ÐN and CÐ Ð ÐN distances are 222.6 and 293.6 pm, respectively, as shown in Table S1 (Supplementary Material).…”

Section: Geometry Optimizationmentioning

confidence: 99%

FT‐Raman, IR and UV‐visible spectral investigations and ab initio computations of a nonlinear food dye amaranth

Snehalatha¹,

Ravikumar²,

Sekar

et al. 2008

J Raman Spectroscopy

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Amaranth (E123, Food Red 9, FD & C Red 2) is a sulfonated azo dye used as a color additive in foodstuffs, pharmaceuticals and cosmetics. FT-IR and FT-Raman spectra of amaranth were recorded and analyzed. Density functional theory (DFT) calculations were performed to derive the equilibrium geometry, vibrational wavenumbers, intensities and first hyperpolarizability. The results of the optimized molecular structure gave clear evidence for the intramolecular charge transfer (ICT) and intramolecular hydrogen bonding in the molecule. Azo stretching wavenumbers are lowered owing to conjugation and p-electron delocalization. Time-dependent density functional theory (TD-DFT) calculations of the electronic spectra were performed on the optimized structure and compared with the experimental UV-visible spectrum. Vibrational spectra, natural bonding orbitals (NBO) analysis and optimized geometry indicate C-H· · ·N hydrogen bonding in the molecule. The first hyperpolarizability of the molecule was calculated. The optical nonlinearity of the dye is due to the donation of the electron density from the hydroxyl group of the conjugated system via naphthalene (2) ring into p * -orbital of the azo moiety.

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Supramolecular motifs in s-block metal bound sulfonated monoazo dyes

Cited by 46 publications

References 17 publications

Structures of five salt forms of disulfonated monoazo dyes

Structures of five salt forms of disulfonated monoazo dyes

Supramolecular Structure in s‐Block Metal Complexes of Sulfonated Monoazo Dyes: Discrepant Packing and Bonding Behavior of ortho‐Sulfonated Azo Dyes

FT‐Raman, IR and UV‐visible spectral investigations and ab initio computations of a nonlinear food dye amaranth

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