Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Co-Crystal Formation of Partially Fluorinated 1,3,5-Tris(phenylethynyl)benzenes.

ABSTRACT: Several rigid 1,3,5-tris(phenylethynyl)benzenes with different fluorination patterns were synthesized through selective Sonogashira-Hagihara coupling reactions to analyze the packing behavior in solid-state structures. The aggregation is dominated by various intermolecular interactions between aryl substituents, triple bonds, C-H bonds and H⋅⋅⋅F contacts. Co-crystallization experiments for the analysis of preferred aryl-aryl-interactions led to 1 : 1 complexes. Intermolecular phenyl-perfluorophenyl interactions with short centroid-centroid distances are dominating these co-crystal structures. They lead to melting point increases of up to 49 °C for the co-crystals compared to the pure substances.

SUBMITTER: Weddeling JH

PROVIDER: S-EPMC8527987 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Co-Crystal Formation of Partially Fluorinated 1,3,5-Tris(phenylethynyl)benzenes.

Weddeling Jan-Henrik JH Waltersmann Paul Lukas PL Neumann Beate B Stammler Hans-Georg HG Mitzel Norbert W NW

ChemistryOpen 20211001 10

Several rigid 1,3,5-tris(phenylethynyl)benzenes with different fluorination patterns were synthesized through selective Sonogashira-Hagihara coupling reactions to analyze the packing behavior in solid-state structures. The aggregation is dominated by various intermolecular interactions between aryl substituents, triple bonds, C-H bonds and H⋅⋅⋅F contacts. Co-crystallization experiments for the analysis of preferred aryl-aryl-interactions led to 1 : 1 complexes. Intermolecular phenyl-perfluorophe ...[more]

PMID: 34669268

Similar Datasets

Synthesis, Crystal Structure, and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5-yl)benzenes.

Project description:Understanding the supramolecular environment of crystal structures is necessary to facilitate designing molecules with desirable properties. A series of 12 novel 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzenes was used to assess the existence of planar stacking columns in supramolecular structures of pyrazoles. This class of molecules with different substituents may assist in understanding how small structural changes affect the supramolecular environment. The obtained compounds did not present the formation of planar stacking interactions between benzenes in solid or liquid states. This supposition was indicated by single crystal diffraction, Density Functional Theory (DFT) and quantum theory of atoms in molecules (QTAIM) calculations, and concentration-dependent liquid-state ¹H nuclear magnetic resonance (NMR). NMR showed that chemical shifts of benzene and pyrazole hydrogens confirm that planar stacking interactions are not formed in solution. The crystalline structures presented different molecular conformations. The molecular structures of 5 and 9b are in a twisted conformation, while compound 7 showed a conformation analogous to a calyx form.

| S-EPMC5943957 | biostudies-literature

Starazo triple switches - synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes.

Project description:Multistate switches allow to drastically increase the information storage capacity and complexity of smart materials. In this context, unsymmetrical 1,3,5-tris(arylazo)benzenes - 'starazos' - which merge three photoswitches on one benzene ring, were successfully prepared. Two different synthetic strategies, one based on Baeyer-Mills reactions and the other based on Pd-catalyzed coupling reactions of arylhydrazides and aryl halides, followed by oxidation, were investigated. The Pd-catalyzed route efficiently led to the target compounds, unsymmetrical tris(arylazo)benzenes. These triple switches were preliminarily characterized in terms of their isomerization behavior using UV-vis and 1H NMR spectroscopy. The efficient synthesis of this new class of unsymmetrical tris(arylazo)benzenes opened new avenues to novel multistate switching materials.

| S-EPMC6964668 | biostudies-literature

Synthesis of 1,4-bis(phenylethynyl)benzenes and their application as blue phase liquid crystal composition.

Project description:A number of 1,4-bis(phenylethynyl)benzene derivatives (BPEBs) and their analogues with different numbers of side-substitute fluorine atoms on benzene rings, and alkyl chains, ethoxyl groups, fluorine atoms and trifluoromethyl groups as the end groups have been synthesized. The effects of the different substituents on their properties such as thermal behavior of melting point and clearing point, the temperature of nematic phase, optical anisotropy and dielectric anisotropy have been well investigated, and it has been found that some BPEBs have a wide range of the nematic phase temperature with high optical anisotropy (?n) and acceptable dielectric anisotropy (??), which have been applied as the crucial compositions to constitute a liquid crystal mixture having the properties of ??=29.0 and ?n=0.283 at 25 °C. With the addition of the chiral dopant to the obtained liquid crystal mixture, blue phase liquid crystal with a blue phase temperature range of 8 °C has been achieved.

| S-EPMC3876042 | biostudies-literature

Crystal structure of 2,4,6-tris-(cyclo-hex-yloxy)-1,3,5-triazine.

Project description:The title compound, C21H33N3O3, is a tri-substituted cyclo-hex-yloxy triazine. In the crystal, the triazine rings form (C3i-PU) Piedfort units. The inter-centroid distance of the π-π inter-action involving the triazine rings is 3.3914 (10) Å. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming ribbons propagating along [1-10]. There are also weak C-H⋯N and C-H⋯O contacts present, linking inversion-related ribbons, forming a three-dimensional structure.

| S-EPMC4645094 | biostudies-literature

Benzene-1,3,5-triyl tris-(methane-sulfonate).

Project description:In the mol-ecule of the title compound, C(9)H(12)O(9)S(3), the two methanesulfonate groups re located one above and one below the ring plane. The C-O-S angle range is 119.3 (2)-121.1 (2)°. This conformation is different from that of the benzene analog 1,2,5-tris-(p-toluene-sulfonate), which is a three-legged 'table' with all fragments of the p-toluene-sulfonate on top of the benzene ring. In the crystal, the supra-molecular aggregation is completed by the presence of C-H⋯O hydrogen bonds.

| S-EPMC2983843 | biostudies-literature

1,3,5-Tris(4-meth-oxy-phen-yl)-1,3,5-triazinane-2,4,6-trione.

Project description:The complete mol-ecule of the title compound, C24H21N3O6, is generated by the application of threefold rotation symmetry about an axis perpendicular to the central ring. The mol-ecule exhibits a propeller-like shape. The dihedral angle between each benzene ring and the heterocyclic ring is 74.0 (1)°. The mol-ecules pack with no specific inter-molecular inter-actions between them. The SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155] was used to model disordered solvent mol-ecules, presumed to be acetone; the calculated unit-cell data do not take into account the presence of these.

| S-EPMC3998286 | biostudies-literature

Benzene-1,3,5-triyl tris-(2,2-dimethyl-propanoate).

Project description:In the title compound, C(21)H(30)O(6), the three acet-oxy groups are essentially planar with their normals rotated by -57.75 (4), -62.36 (4) and 63.36 (4)° from the normal to the mean plane of the C(6) ring. The arrangement of carbonyl groups around the ring is of two groups 'up' and one 'down', and the propeller-style arrangement of substituent groups is spoiled with the plane of the 'down' group twisted in the opposite direction; all the C(ring)-O-C-CMe(3 )conformations are trans. In the crystal, aromatic π-π stacking occurs [centroid-centroid separation = 3.320 (1) Å]; the other main inter-molecular inter-action is a C-H⋯π-ring contact on the opposing side from the overlapped ring pairing; there are no short C-H⋯O contacts.

| S-EPMC2971883 | biostudies-literature

1,3,5-Tris(4-bromo-phen-yl)-1,3,5-triazin-ane di-chloro-methane monosolvate.

Project description:In the main mol-ecule of the title compound, C21H18Br3N3·CH2Cl2, the triazinane ring adopts a chair conformation with three 4-brom-ophenyl substituents, two in diaxial positions and the third in an equatorial arrangement (eaa). The torsion angles around the N-C bonds in the triazinane ring are in the range 55.6?(5)-60.1?(5)°. The structure can be described as being built up of alternating layers along the b axis with the CH2Cl2 solvent mol-ecules sandwiched between these layers. No classical hydrogen-bonding inter-actions are observed in the crystal structure.

| S-EPMC3685111 | biostudies-literature

2,4,6-Trimethyl-1,3,5-tris-(morpholino-meth-yl)benzene.

Project description:In the title compound, C(24)H(39)N(3)O(3), the H atoms of the methyl groups are disordered over two positions, with site-occupation factors fixed at 0.5. The three morpholino groups are arranged in an asymmetrical fashion with respect to the anchoring mesitylene ring and adopt chair conformations. Inter-molecular C-H⋯π inter-actions link the mol-ecules into a one-dimensional chain structure.

| S-EPMC2961465 | biostudies-literature

2,4,6-Tris(2,4-dimethyl-phen-yl)-1,3,5-triazine.

Project description:Two virtually superimposable mol-ecules comprise the asymmetric unit of the title compound, C(27)H(27)N(3). The range of dihedral angles between the central 1,3,5-triazine ring and the attached benzene rings is 20.88?(14)-31.36?(14)°, and the shape of each mol-ecule is of a flattened bowl. The crystal packing features weak C-H?? bonds and ?-? inter-actions between triazine and benzene rings [centroid-centroid separations = 3.7696?(17) and 3.7800?(18)?Å] that result in the formation of supra-molecular layers in the ac plane. The crystal studied was a non-merohedral twin with a minor twin component of 20.7?(3)%.

| S-EPMC3344576 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data