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From Hexaphenylbenzene to 1,2,3,4,5,6-Hexacyclohexylcyclohexane.

ABSTRACT: The hydrogenation of hexaphenylbenzene was studied, affording novel partially hydrogenated hexacyclohexylbenzene (HCB) as well as fully hydrogenated 1,2,3,4,5,6-hexacyclohexylcyclohexane (HCC) as an unprecedented "oligocyclohexyl" molecule. The reaction process was analyzed by mass spectrometry with atmospheric pressure chemical ionization and high-performance liquid chromatography. From a crude product mixture, two different crystals with flake- and block-shapes could be grown and analyzed by X-ray crystallography, revealing their structures as HCB and HCC. While a geared arrangement of cyclohexyl substitutes was found in HCB, two isomeric structures were identified in HCC crystal with chair and twist-boat conformations of the central cyclohexane.

SUBMITTER: Dillenburger M

PROVIDER: S-EPMC7458423 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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From Hexaphenylbenzene to 1,2,3,4,5,6-Hexacyclohexylcyclohexane.

Dillenburger Marcel M Qiu Zijie Z Ju Cheng-Wei CW Müller Beate B Morsbach Svenja S Schollmeyer Dieter D Narita Akimitsu A Müllen Klaus K

Journal of the American Chemical Society 20200720 30

The hydrogenation of hexaphenylbenzene was studied, affording novel partially hydrogenated hexacyclohexylbenzene (<b>HCB</b>) as well as fully hydrogenated 1,2,3,4,5,6-hexacyclohexylcyclohexane (<b>HCC</b>) as an unprecedented "oligocyclohexyl" molecule. The reaction process was analyzed by mass spectrometry with atmospheric pressure chemical ionization and high-performance liquid chromatography. From a crude product mixture, two different crystals with flake- and block-shapes could be grown and ...[more]

PMID: 32668154

Similar Datasets

Correction to "From Hexaphenylbenzene to 1,2,3,4,5,6-Hexacyclohexylcyclohexane".

Project description: Not available

| S-EPMC7853618 | biostudies-literature

1,2,3,4,5,6-Hexa-O-acetyl-scyllo-inositol.

Project description:The title mol-ecule, C(18)H(24)O(12), has crystallographic 2/m symmetry with two acetate group located on a mirror plane. The H-Csp(3)-O-Csp(2) torsion angles characterizing orientation of the acetyl groups with respect to the cyclo-hexane ring are 0.0, 23.9 and -23.9°. The cyclo-hexane ring is in a chair conformation with all substituents in equatorial positions. In the crystal, mol-ecules are connected through C-H?O hydrogen bonds into a chain extending along the c axis.

| S-EPMC3415030 | biostudies-literature

Structure Formation and Coupling Reactions of Hexaphenylbenzene and Its Brominated Analog.

Project description:The on-surface coupling of the prototypical precursor molecule for graphene nanoribbon synthesis, 6,11-dibromo-1,2,3,4-tetraphenyltriphenylene (C42 Br2 H26 , TPTP), and its non-brominated analog hexaphenylbenzene (C42 H30 , HPB), was investigated on coinage metal substrates as a function of thermal treatment. For HPB, which forms non-covalent 2D monolayers at room temperature, a thermally induced transition of the monolayer's structure could be achieved by moderate annealing, which is likely driven by π-bond formation. It is found that the dibrominated carbon positions of TPTP do not guide the coupling if the growth occurs on a substrate at temperatures that are sufficient to initiate C-H bond activation. Instead, similar one-dimensional molecular structures are obtained for both types of precursors, HPB and TPTP.

| S-EPMC8456788 | biostudies-literature

Hexaphenylbenzene as a rigid template for the straightforward syntheses of "star-shaped" glycodendrimers.

Project description:Original glycodendrimers emanating from propargylated hexaphenylbenzene cores and containing up to 54 peripheral sugar ligands have been synthesized by Cu(I)-catalyzed [1,3]-dipolar cycloadditions using both convergent and divergent approaches.

| S-EPMC3981551 | biostudies-literature

?-extended [12]cycloparaphenylenes: from a hexaphenylbenzene cyclohexamer to its unexpected C2-symmetric congener.

Project description:The synthesis of ?-extended [12]cycloparaphenylene (CPP) derivatives from a kinked triangular macrocycle is presented. Depending on the reaction conditions for reductive aromatization, either a hexaphenylbenzene cyclohexamer or its C2-symmetric congener was obtained. Their structures were confirmed by NMR spectroscopy or X-ray crystallographic analysis. With the support of DFT calculations, a mechanistic explanation for the unexpected formation of the oval shaped bis(cyclohexadiene)-bridged C2-symmetric macrocycle is provided. The here employed congested hexaphenylbenzene mode of connectivity in conjunction with a non-strained precursor improves oxidative cyclodehydrogenation toward the formation of ultrashort carbon nanotubes (CNT)s. Thus, this strategy can pave the way for new conceptual approaches of a solution-based bottom-up synthesis of CNTs.

| S-EPMC5510010 | biostudies-literature

Poly[hexa-aqua-(μ9-cyclo-hexane-1,2,3,4,5,6-hexa-carboxyl-ato)trimanganese(II)].

Project description:The asymmetric unit of the title compound, [Mn3(C12H6O12)(H2O)6] n , comprises one Mn(II) ion, one third of a cyclo-hexane-1,2,3,4,5,6-hexa-carboxyl-ate anion and two aqua ligands. The anion is completed by application of a -3 axis. The Mn(II) ion is six-coordinated by six O atoms from two aqua ligands and three different cyclo-hexa-carboxyl-ate anions in an octa-hedral geometry. The six carboxyl-ate groups adopt a bridging bidentate mode to ligate the Mn(II) ions. Thus, each cyclo-hexane-1,2,3,4,5,6-hexa-carboxyl-ate anion adopts a μ9-connected mode, ligating nine different Mn(II) ions and forming a three-dimensional framework. In the framework, there are strong O-H⋯O hydrogen-bonding inter-actions, which further stabilize the crystal structure.

| S-EPMC3772420 | biostudies-literature

A Functional Hexaphenylbenzene Library Comprising of One, Three, and Six Peripheral Rylene-Diimide Substituents.

Project description:Synthesis and characterization of a series of rylene-diimide substituted hexaphenylbenzenes (HPBs) is presented. The direct connection of the rylene-diimide units to the HPBs via the imide-N-position without any linkers as well as the use of naphthalene-diimides (NDIs) next to perylene-diimides (PDIs) is unprecedented. While mono-substituted products were obtained by imidization reactions with amino-HPB and the respective rylene-monoimides, key step for the formation of tri- and hexa-substituted HPBs is the Co-catalysed cyclotrimerization. Particular emphasis for physic-chemical characterization was on to the number of NDIs/PDIs per HPB and the overall substitution patterns. Lastly, Scholl oxidation conditions were applied to all HPB systems to generate the corresponding hexa-peri-hexabenzocoronenes (HBCs). Importantly, the efficiency of the transformation strongly depends on the number of NDIs/PDIs. While three rylene-diimide units already hinder the Scholl reaction, the successful synthesis of mono-substituted HBCs is possible.

| S-EPMC7898621 | biostudies-literature

Janus Face All-cis 1,2,4,5-tetrakis(trifluoromethyl)- and All-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)- Cyclohexanes.

Project description:We report the synthesis of all-cis 1,2,4,5-tetrakis (trifluoromethyl)- and all-cis 1,2,3,4,5,6-hexakis (trifluoromethyl)- cyclohexanes by direct hydrogenation of precursor tetrakis- or hexakis- (trifluoromethyl)benzenes. The resultant cyclohexanes have a stereochemistry such that all the CF3 groups are on the same face of the cyclohexyl ring. All-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)cyclohexane is the most sterically demanding of the all-cis hexakis substituted cyclohexanes prepared to date, with a barrier (ΔG) to ring inversion calculated at 27 kcal mol-1 . The X-ray structure of all-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)cyclohexane displays a flattened chair conformation and the electrostatic profile of this compound reveals a large diffuse negative density on the fluorine face and a focused positive density on the hydrogen face. The electropositive hydrogen face can co-ordinate chloride (K≈103 ) and to a lesser extent fluoride and iodide ions. Dehydrofluorination promoted decomposition occurs with fluoride ion acting as a base.

| S-EPMC7693182 | biostudies-literature

Poly[di-ammonium [di-aqua-(μ7-benzene-1,2,3,4,5,6-hexa-carboxyl-ato)tetra-oxido-diuranium(VI)]].

Project description:Uranyl-carboxyl-ate hybrid materials dominate the catalog of uranyl compounds owing in part to the affinity between COO(-) functional groups and UO2 (2+). Polycarboxyl-ate organic ligands may present a degree of steric hindrance and could thus influence the resulting uranyl topology. Single crystals of the title compound, {(NH4)2[(UO2)2(C12O12)(H2O)2]} n , were synthesized hydro-thermally as a result of reacting uranyl nitrate with benzene-1,2,3,4,5,6-hexa-carb-oxy-lic acid (mellitic acid). The structure is comprised of a single unique monomeric uranyl cation adopting a penta-gonal bipyramidal geometry. The uranyl coordination sphere is composed of four O atoms originating from one half of a fully deprotonated mellitic acid ligand and a single water mol-ecule. The observed axial U-O bonds display an average distance of 1.765 (8) Å, whereas equatorial O atoms are found at an average distance of 2.40 (5) Å. All uranium-oxygen bond lengths are in good agreement with literature values. Furthermore, the coordin-ation between the uranyl penta-gonal bipyramids and the mellitic acid anion constructs a three-dimensional anionic framework which is charge-balanced with ammonium cations. Additional stabilization of the structure is provided by O-H⋯O and N-H⋯O hydrogen bonding inter-actions between the components.

| S-EPMC3998547 | biostudies-literature

1-(2-Chloro-1,3-thia-zol-5-ylmeth-yl)-3,5-dimethyl-2-nitrimino-1,2,3,4,5,6-hexa-hydro-1,3,5-triazine.

Project description:In the title compound, C(9)H(13)ClN(6)O(2)S, all bond lengths and angles are normal. The 1,3,5-triazine ring exhibits a half-chair conformation. In the crystal structure, weak inter-molecular C-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane.

| S-EPMC2915191 | biostudies-literature

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