Sinusoidal ribbon waves in the crystal structure of bis(4-aminophenyl)disulfide

Vittal, Jagadese J.; Anjali, K.S.

doi:10.1016/s0025-5408(98)00089-0

Cited by 6 publications

(9 citation statements)

References 18 publications

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“…This morphology is clarified by the powder X‐ray diffraction (PXRD) analysis. The PXRD data reveal lattice parameters very similar to those found for the bis ( 4 ‐aminophenyl)disulfide in the Cambridge Structural Database25 (Supporting Information Table S1). Views of the crystal structure and molecular packing are shown in Figure 4d‐f.…”

Section: Resultssupporting

confidence: 54%

“…First, the addition of p‐ ATP in ethanol to water results in a spontaneous oxidation of the thiol group and formation of a disulfide bond, leading to the conversion of the monomer p‐ ATP to p‐ aminophenyl disulfide ( p‐ APDS) ( Figure ). This conversion can also be obtained with air oxidation, although it requires a much longer time and does not induce the mechanism described here 25, 26. The oxidation is instantly followed by the aggregation of p‐ APDS into clusters that can or not, pending conditions, evolve into micelles and vesicles.…”

Section: Resultsmentioning

confidence: 79%

“…Quantitative Rietveld refinement of PXRD pattern was carried out using TOPAS software (version 3) and the results are plotted in Supporting Figure 4. The structures of p‐ APDS25 and the 1:1 molecular complex of p‐ APDS and p‐ ATP26 were obtained from Cambridge Crystal Structure Database (CCDC) and their CIF files were used as reference to carry out the refinement of the PXRD pattern of p‐ APDS microtubes. The experimentally observed pattern of the assembled p‐ APDS microtubes are shown as circles and the fitted data are shown as a red line.…”

Section: Methodsmentioning

confidence: 99%

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Vesicle‐Mediated Growth of Tubular Branches and Centimeter‐Long Microtubes from a Single Molecule

Abbas

Brimer

Tian

et al. 2012

Small

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The mechanism by which small molecules assemble into microscale tubular structures in aqueous solution remains poorly understood, particularly when the initial building blocks are non-amphiphilic molecules and no surfactant is used. It is here shown how a subnanometric molecule, namely p-aminothiophenol (p-ATP), prepared in normal water with a small amount of ethanol, spontaneously assembles into a new class of nanovesicle. Due to Brownian motion, these nanostructures rapidly grow into micrometric vesicles and start budding to yield macroscale tubular branches with a remarkable growth rate of ∼20 μm s⁻¹. A real-time visualization by optical microscopy reveals that tubular growth proceeds by vesicle walk and fusion on the apex (growth cone) and sides of the branches and ultimately leads to the generation of centimeter-long microtubes. This unprecedented growth mechanism is triggered by a pH-activated proton switch and maintained by hydrogen bonding. The vesicle fusion-mediated synthesis suggests that functional microtubes with biological properties can be efficiently prepared with a mixture of appropriate diaminophenyl blocks and the desired macromolecule. The reversibility, timescale, and very high yield (90%) of this synthetic approach make it a valuable model for the investigation of hierarchical and structural transition between organized assemblies with different size scales and morphologies.

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Section: Resultssupporting

confidence: 54%

Section: Resultsmentioning

confidence: 79%

Section: Methodsmentioning

confidence: 99%

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Vesicle‐Mediated Growth of Tubular Branches and Centimeter‐Long Microtubes from a Single Molecule

Abbas

Brimer

Tian

et al. 2012

Small

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“…The C-S-S-C torsion angles in aromatic disulfide groups are known to be within about 208 of 908. [29,30] Thus, the disulfide moiety in the spacer ligand seems to maintain its characteristic shape even after bonding to the Zn II center. The two carbonyl oxygen atoms are involved in intramolecular CÀH···O bonding to [b] 1.00 (2) 1.77(2) 2.76 (1) 168 (1) [a] Symmetry operator: Àx + 2, Ày, Àz.…”

Section: And O(3) Each Of Which Has a Weak Intramolecular Interactiomentioning

confidence: 99%

Hydrogen‐Bonded Polyrotaxane‐like Structure Containing Cyclic (H₂O)₄ in [Zn(OAc)₂(μ‐bpe)]⋅2 H₂O: X‐ray and Neutron Diffraction Studies

Deivaraj

Klooster

et al. 2004

Chemistry A European J

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The reaction of 4,4'-bipyridylethane (bpe) and 4,4'-dipyridyl disulfide (dpds) with Zn(OAc)2.2H2O has led to the formation of two coordination polymers, [Zn(OAc)2(mu-bpe)].2H2O (1) and [Zn(OAc)2(mu-dpds)] (2). Both the compounds have zigzag coordination polymeric structures as revealed by X-ray crystallography. However, the presence of two lattice water molecules in 1 results in an interesting difference between the crystal structures. In 1, the carboxylate carbonyl oxygen atoms of the Zn(OAc)2 groups from two different adjacent zigzag polymers and four lattice water molecules form 24-membered hydrogen-bonded rings (graph set notation, R6 (6)(24)). One of the two bpe ligands associated with each Zn(II) center passes through the center of this ring to form a two-dimensional hydrogen-bonded coordination polymeric structure. In the solid state, the adjacent 24-membered hydrogen-bonded rings further fuse together through O-H...O hydrogen bonds among four waters to form cyclic (H2O)4. This results in a one-dimensional hydrogen-bonded ribbon-like polymer comprising fused alternating 24- and eight-membered O-H...O hydrogen-bonded rings. One of the bpe ligands passes through the center of the larger ring to produce an unexpected single self-penetrating three-dimensional hydrogen-bonded network with polyrotaxane-like association. A neutron diffraction study provides a detailed description of the hydrogen bonds involved.

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“…The crystal lattice had disordered water molecules (not shown in Figure 2). The crystal structure of 4-ATP alone reveals no similar arrangements of the aromatic rings [17]. Figure 3 shows the packing diagram of pure 4-ATP crystal and the 4-ATP as guest molecule in the lattice of 4-ATP/β-CD complex.…”

Section: Scheme 1 Modification Of 4-atp To 44'-diaminodiphenyl Disumentioning

confidence: 99%

Host–Guest Complex of β-Cyclodextrin and Disulfide Form of 4-Aminothiophenol

Cappadona

Daniels²,

Siddiquee

2012

Applied Sciences

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An inclusion complex of β-cyclodextrin and 4-aminothiophenol was assembled by hydrophobic interaction of the host (β-cyclodextrin) and guest (4-aminothiophenol). The complex was isolated as crystalline solid and studied by single crystal X-ray diffraction method along with NMR and IR spectroscopy. Two cyclodextrin rings each containing one disulfide form of 4-aminothiophenol were found to pair up by hydrogen bonding of the outer rim -OH groups. The phenyl disulfide moiety of 4-aminophenyl disulfide molecule was found in the core of β-cyclodextrin, while the amino functional groups were positioned to the exterior of the cyclodextrin ring. Phenyl rings of the guest molecule from each partner of the paired cyclodextrin complex were found parallel to each other, indicating possible π-π stacking interaction between them.

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Sinusoidal ribbon waves in the crystal structure of bis(4-aminophenyl)disulfide

Cited by 6 publications

References 18 publications

Vesicle‐Mediated Growth of Tubular Branches and Centimeter‐Long Microtubes from a Single Molecule

Vesicle‐Mediated Growth of Tubular Branches and Centimeter‐Long Microtubes from a Single Molecule

Hydrogen‐Bonded Polyrotaxane‐like Structure Containing Cyclic (H₂O)₄ in [Zn(OAc)₂(μ‐bpe)]⋅2 H₂O: X‐ray and Neutron Diffraction Studies

Host–Guest Complex of β-Cyclodextrin and Disulfide Form of 4-Aminothiophenol

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Sinusoidal ribbon waves in the crystal structure of bis(4-aminophenyl)disulfide

Cited by 6 publications

References 18 publications

Vesicle‐Mediated Growth of Tubular Branches and Centimeter‐Long Microtubes from a Single Molecule

Vesicle‐Mediated Growth of Tubular Branches and Centimeter‐Long Microtubes from a Single Molecule

Hydrogen‐Bonded Polyrotaxane‐like Structure Containing Cyclic (H2O)4 in [Zn(OAc)2(μ‐bpe)]⋅2 H2O: X‐ray and Neutron Diffraction Studies

Host–Guest Complex of β-Cyclodextrin and Disulfide Form of 4-Aminothiophenol

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Hydrogen‐Bonded Polyrotaxane‐like Structure Containing Cyclic (H₂O)₄ in [Zn(OAc)₂(μ‐bpe)]⋅2 H₂O: X‐ray and Neutron Diffraction Studies