C–I···π Halogen Bonding Driven Supramolecular Helix of Bilateral <i>N</i>-Amidothioureas Bearing β-Turns

Cao, Jinlian; Yan, Xiaosheng; He, Wen-Bin; Li, Xiaorui; Li, Zhao; Mo, Yirong; Liu, Maili

doi:10.1021/jacs.6b13171

Cited by 111 publications

(99 citation statements)

References 54 publications

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“…These dimers are further linked tail-to-head between alkyl segments via van der Waals force to give 1D zig-zag packing.T he 1D packing arrays along the b axis adopt a P-type handedness from the amplification of intrinsic molecular chirality of cholesterol domains. [26,27] Most of integrated WAXS peaks for 2aand 2ccould be assigned according to the comparison with simulated XRD patterns (Supporting Information, Figures S13 and S14), revealing ag ood agreement between their crystal structures and self-assemblies in decane.…”

Section: Angewandte Chemiementioning

confidence: 91%

Water‐Binding‐Mediated Gelation/Crystallization and Thermosensitive Superchirality

Xing

Wang

et al. 2018

Angew Chem Int Ed

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Determination of molecular structural parameters of hydrophobic cholesterol-naphthalimide conjugates for water binding capabilities as well as their moisture-sensitive supramolecular self-assembly were revealed. Water binding was a key factor in leading trace water-induced crystallization against gelation in apolar solvent. Ordered water molecules entrapped in self-assembly arrays revealed by crystal structures behave as hydrogen-bonding linkers to facilitate three-dimensional growth into crystals rather than one-dimensional gel nanofibers. Water binding was also reflected on the supramolecular chirality inversion of vesicle self-assembly in aqueous media via heating-induced dehydration. Structural parameters that favor water binding were evaluated in detail, which could help rationally design organic building units for advancing soft materials, crystal engineering, and chiral recognition.

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Section: Angewandte Chemiementioning

confidence: 91%

Water‐Binding‐Mediated Gelation/Crystallization and Thermosensitive Superchirality

Xing

Wang

et al. 2018

Angew Chem Int Ed

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“…. π interactions, while other inter-helices XBs create a complex network [93]. Substituting iodine with chloride, helical structures do not form in the solid state.…”

Section: Nuclear Overhauser Effectmentioning

confidence: 99%

“…An X-ray of the crystal structure demonstrated that the monomer self-organizes in supramolecular helices held together by iodine…π interactions, while other inter-helices XBs create a complex network [93]. Substituting iodine with chloride, helical structures do not form in the solid state.…”

Section: Nuclear Overhauser Effectmentioning

confidence: 99%

Characterization of Halogen Bonded Adducts in Solution by Advanced NMR Techniques

Ciancaleoni

2017

Magnetochemistry

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Abstract:In the last 20 years, a huge volume of experimental work into halogen bonding (XB) has been produced. Most of the systems have been characterized by solid state X-ray crystallography, whereas in solution the only routine technique is titration (by using 1 H and 19 F nuclear magnetic resonance (NMR), infrared (IR), ultraviolet-visible (UV-Vis) or Raman spectroscopies, depending on the nature of the system), with the aim of characterizing the strength of the XB interaction. Unfortunately, titration techniques have many intrinsic limitations and they should be coupled with other, more sophisticated techniques to provide an accurate and detailed description of the geometry and stoichiometry of the XB adduct in solution. This review will show how crucial information about XB adducts can be obtained by advanced NMR techniques, nuclear Overhauser effect-based spectroscopies (NOESY, ROESY, HOESY . . . ) and diffusion NMR techniques (PGSE or DOSY).

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“…X-ray crystal structure demonstrated that the monomer self-organizes in supramolecular helices held together by iodine … π interactions, while other inter-helices XBs create a complex network. [54] Substituting iodine with chloride, helical structures do not form in the solid state. Comparing X-ray structures with NOESY spectra, the authors deduced that when X = Cl (LL-ACl), only intramolecular NOE contacts are visible and, in particular, the e-f contact is well visible (internuclear e-f distance in the solid-state structure: 3.189 Å) and the e-g is not (internuclear e-g distance in the solid-state structure: 4.348 Å, Figure 8).…”

Section: Nuclear Overhauser Effectmentioning

confidence: 99%

Characterization of Halogen Bonded Adducts in Solution by Advanced NMR Techniques

Ciancaleoni¹

2017

Preprint

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Abstract:In the last 20 years, a huge amount of experimental results about halogen bonding (XB) has been produced. Most of the systems have been characterized by solid state X-ray crystallography, whereas in solution the only routine technique is the titration (by using 1 H and 19 F NMR, IR, UV-Vis or Raman spectroscopies, depending on the nature of the system), with the aim of characterizing the strength of the XB interaction. Unfortunately, the titration techniques have many intrinsic limitations and they should be coupled with other, more sophisticated techniques to have an accurate and detailed description of the geometry and stoichiometry of the XB adduct in solution. In this review, it will be shown how crucial information about XB adducts can be obtained by advanced NMR techniques, as Nuclear Overhauser Effect-based Spectroscopies (NOESY, ROESY, HOESY…) and diffusion NMR techniques (PGSE or DOSY).

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C–I···π Halogen Bonding Driven Supramolecular Helix of Bilateral N-Amidothioureas Bearing β-Turns

Cited by 111 publications

References 54 publications

Water‐Binding‐Mediated Gelation/Crystallization and Thermosensitive Superchirality

Water‐Binding‐Mediated Gelation/Crystallization and Thermosensitive Superchirality

Characterization of Halogen Bonded Adducts in Solution by Advanced NMR Techniques

Characterization of Halogen Bonded Adducts in Solution by Advanced NMR Techniques

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