Cubic aggregation: The racemic C(3)-symmetrical tribenzotriquinacene 1 was synthesized and found to crystallize in cubic aggregates consisting of eight homochiral molecules. The major driving force for this unique supramolecular aggregation may be attributed to the 24 equivalent sub-van der Waals interactions between the bromine atoms located at the convex surface of the triquinacene cores, rather than to polar interactions between the nitrobenzene units within and between the nanocubes.
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Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration.
Phys Chem Chem Phys
April 2016
Department of Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany.
The solid-state molecular structure of centrohexaindane (), a unique hydrocarbon comprising six benzene rings clamped to each other in three dimensions around a neopentane core, and the molecular packing in crystals of ·CHCl3 are reported. The molecular Td-symmetry and the Cartesian orientation of the six indane wings of in the solid state have been confirmed. The course and limitation of electrophilic aromatic substitution of are demonstrated for the case of nitration.
View Article and Find Full Text PDFRegiocontrolled synthesis and optical resolution of mono-, di-, and trisubstituted tribenzotriquinacene derivatives: key building blocks for further assembly into molecular squares and cubes.
J Org Chem
October 2014
Department of Chemistry, Center of Novel Functional Materials and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong SAR.
The regiocontrolled syntheses of four chiral C1- or C3-symmetrical tribenzotriquinacene (TBTQ) derivatives bearing methoxy or hydroxy groups at the peripheral positions [(2,6-(OMe)2, (±)-18 and (±)-20; 2,6-(OH)2, (±)-19; and 2,6,10-(OMe)3, (±)-21] by two different synthesis protocols are reported. Compounds (±)-19, (±)-20, and (±)-21 and two (already-known) monosubstituted C1-symmetrical TBTQ analogues [2-OH (±)-23 and 2-OMe (±)-24] were readily resolved by chiral HPLC, and their absolute configurations were determined by X-ray crystallography and/or circular dichroism (CD) studies. Optical resolution of three closely related TBTQ derivatives [2,6-(OMe)2, (±)-18; 2-OMe, (±)-22; and 2-OH, (±)-25] containing the same peripheral substituents but other bridgehead residues failed.
View Article and Find Full Text PDFTribenzotriquinacene receptors for C60 fullerene rotors: towards C3 symmetrical chiral stators for unidirectionally operating nanoratchets.
Chemistry
July 2014
Augsburg University, Institute of Physics, Chair of Solid State and Materials Chemistry, Universitätsstrasse 1, 86159 Augsburg (Germany).
The synthesis of a stereochemically pure concave tribenzotriquinacene receptor (7) for C60 fullerene, possessing C3 point group symmetry, by threefold condensation of C2 -symmetric 1,2-diketone synthons (5) and a hexaaminotribenzotriquinacene core (6) is described. The chiral diketone was synthesized in a five-step reaction sequence starting from C2h -symmetric 2,6-di-tert-butylanthracene. The highly diastereo-discriminating Diels-Alder reaction of 2,6-di-tert-butylanthracene with fumaric acid di(-)menthyl ester, catalyzed by aluminium chloride, is the relevant stereochemistry introducing step.
View Article and Find Full Text PDFC3-symmetrical tribenzotriquinacene derivatives: optical resolution through cryptophane synthesis and supramolecular self-assembly into nanotubes.
J Org Chem
February 2013
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. China.
Based on a regioselective tris-formylation of a tribenzotriquinacene (TBTQ) hydrocarbon, the racemic C(3)-symmetrical TBTQ-trialdehyde and the corresponding TBTQ-trimethanol were synthesized along with their C(1)-isomers. Conversion of the C(3)-trialdehyde to three diastereomeric TBTQ-based cryptophanes occurring in high yield enabled the preparation of the optically pure C(3)-symmetrical TBTQ-trialdehydes and the determination of their absolute configuration. The racemic C(3)-symmetrical TBTQ-trimethanol was found to form several stable nanotubular aggregates in the solid state.
View Article and Find Full Text PDFSolid-state enantiopure organic nanocubes formed by self organization of a C3-symmetrical tribenzotriquinacene.
Chemistry
June 2009
Department of Chemistry, Bielefeld University, Universitätsstrasse 25, 33615 Bielefeld, Germany.
Cubic aggregation: The racemic C(3)-symmetrical tribenzotriquinacene 1 was synthesized and found to crystallize in cubic aggregates consisting of eight homochiral molecules. The major driving force for this unique supramolecular aggregation may be attributed to the 24 equivalent sub-van der Waals interactions between the bromine atoms located at the convex surface of the triquinacene cores, rather than to polar interactions between the nitrobenzene units within and between the nanocubes.
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