Complexation with diol host compounds. Part 10. Synthesis and solid state inclusion properties of bis(diarylhydroxymethyl)-substituted benzenes and biphenyls; X-ray crystal structures of two host polymorphs and of a non-functional host analogue

Weber, Edwin; Skobridis, Konstantinos; Wierig, Andreas; Nassimbeni, Luigi R.; Johnson, Louise

doi:10.1039/p29920002123

Cited by 42 publications

(33 citation statements)

References 14 publications

(2 reference statements)

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“…An important feature of the TADDOL structure is rigidity, owing to the presence of the 1,3-dioxolane ring; structural rigidity is a property frequently associated with effective host compounds. 4 However, in TETROL the conformational mobility usually associated with a butane chain could be significantly constrained as a result of intramolecular hydrogen bonding between the hydroxy groups. The expected favourable 1,3-interactions are shown in 2a and 2b; 1,2-and 1,4-interactions are also possible, as exemplified by 2c.…”

Section: Introductionmentioning

confidence: 99%

A computational, X-ray crystallographic and thermal stability analysis of TETROL and its pyridine and methylpyridine inclusion complexes

et al. 2013

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Section: Introductionmentioning

confidence: 99%

A computational, X-ray crystallographic and thermal stability analysis of TETROL and its pyridine and methylpyridine inclusion complexes

et al. 2013

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“…the replacement of the terminal aryl moieties by heteroaromatic units has been carried out. 17 Thereby, substitutions of phenyl groups in the parent structure 1 18,19 against 2-pyridyl or 2-thienyl residues ( Fig. 1) have been executed.…”

Section: Introductionmentioning

confidence: 99%

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

Katzsch

Gruber

Weber

2015

Crystal Growth & Design

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By applying the 'wheel-and-axle' host concept and incorporating a previously developed heteroaromatic substitution strategy, a new type of diol hosts featuring two di(benzo [b]thien-2-yl)hydroxymethyl units attached to both ends of a central ethynylene (3) and 1,4-phenylene (4) moiety is reported. The syntheses of the host compounds are described and solvent inclusion formation via crystallization has extensively been studied showing a remarkable inclusion capability of the compounds. X-ray diffraction analysis of relevant crystal structures have been performed and comparatively discussed. Vapor sorption behavior of the compounds as solid receptor films coated on a quartz crystal microbalance considering a variety of solvent vapors has been scrutinized, indicating potential application as mass sensitive materials.3

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“…Crystal structures and thermodynamic data: The pure host compound crystallizes in two polymorphic forms, [4] a 1 and a 2 . The first melts at 186.8 8C with an enthalpy of melting of 36.6 kJ mol À1 , with some differential scanning calorimetry (DSC) features that may suggest a phase change.…”

Section: Resultsmentioning

confidence: 99%

“…We became recently acquainted with the multiform solid-state behaviour of the title compound: pure DHMB crystallizes in two polymorphs. [4] Also it can incorporate a number of different guest molecules to yield crystalline inclusion compounds, [5] which may revert to the pure crystal when heated, upon loss of the guests. While X-ray structural characterizations and thermal analysis give a wealth of information on the interconversions, the problem is at the borderline of computational affordability, due to the size and shape of the DHMB host molecule.…”

Section: Introductionmentioning

confidence: 99%

A Molecular Dynamics Study of the Structure and Evolution of the 4,4′-Bis(diphenylhydroxymethyl)biphenyl/Acetone Host-Guest System

Gavezzotti

2000

Chem. Eur. J.

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The 4,4'-bis(diphenylhydroxymethyl)biphenyl/acetone (DHMB-Ac) system was studied by NPT molecular dynamics (MD) calculations; the study was prompted by the availability of X-ray single-crystal diffraction and calorimetric data (L. Johnson, L. Nassimbeni, E. Weber and K. Skobridis, J. Chem. Soc. Perkin Trans. 2, 1992, 2131). Potential energies were calculated by using the UNI-FF or the OPLS all-atom force fields. The kinetics of formation of hydrogen-bonded aggregates between the DHMB molecule and acetone was sampled, and the persistence and fluxionality of the O-H...O=C hydrogen bond are clearly revealed. Extensive MD runs at variable temperature on the inclusion compound in its crystalline state allow a description of the thermal motion and eventual reorientation within its cavity of the acetone molecule; the host crystalline matrix does not survive when guests are removed. The dynamic evolution of a slab of 60 DHMB and 120 acetone molecules. which has the experimental crystal structure, was also simulated at the temperature experimentally observed for guest desorption, and the loss of solvent molecules was monitored. Crystalline order is very quickly lost; then, guest molecules can easily diffuse away from the surface without a noticeable swelling of the material. The molecular reorganization of the remaining host liquid back to the crystal structure of one of the two polymorphs of pure DHMB could not be observed, owing to the short simulation times and to the smallness of the computational sample.

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Complexation with diol host compounds. Part 10. Synthesis and solid state inclusion properties of bis(diarylhydroxymethyl)-substituted benzenes and biphenyls; X-ray crystal structures of two host polymorphs and of a non-functional host analogue

Cited by 42 publications

References 14 publications

A computational, X-ray crystallographic and thermal stability analysis of TETROL and its pyridine and methylpyridine inclusion complexes

A computational, X-ray crystallographic and thermal stability analysis of TETROL and its pyridine and methylpyridine inclusion complexes

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

A Molecular Dynamics Study of the Structure and Evolution of the 4,4′-Bis(diphenylhydroxymethyl)biphenyl/Acetone Host-Guest System

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