N2 - Two imine-based shape-persistent macrocycles containing triphenylene building blocks, along with their noncyclic model compounds, have been synthesized. Their stable conformations are predicted by quantum mechanical calculations and confirmed by 2D NOESY NMR measurements. Compared to the noncyclic model compounds, the macrocycles (3 and 6) show a higher propensity for solution self-assembly due to their stronger π-π stacking interactions, and form micro-objects which exhibit an enhanced conductivity after doping. While both macrocycles have identical molecular geometries and very similar structures, their solution self-assembly leads to micro-objects with very different shapes. The two macrocycles also show different pH-dependent optical properties.
N2 - The synthesis of triphenylene 1,2-oxide (1,2-epoxy-1,2-dihydrotriphenylene) (2) from both racemic and optically pure precursors is reported. Racemic triphenylene 1,2-oxide (2) was obtained in each case, in accord with PMO calculations which predict rapid racemization. Liver microsomal metabolism of both triphenylene (1) and racemic triphenylene 1,2-oxide (2) yielded predominantly the (-)-enantiomer (92 and 85%, respectively) of the trans-dihydro diol (5). The 1R,2R configuration for (-)-(5) has been established by preparative h.p.l.c. separation of the dimenthyloxyacetate diastereoisomers of the dihydro diol (5) and stereochemical correlation to (-)-(1R,2R)-trans-2- bromo-1-menthyloxyacetoxy-1,2,3,4-tetrahydrotriphenylene (9A) whose absolute configuration has been assigned by X-ray crystallographic analysis.
An Improved Synthetic Route to Rigid Triphenylene …
Synthesis and Liquid Crystalline Behavior of Side Chain Liquid Crystalline Polymers Containing Triphenylene Discotic Mesogens with Different Length Flexible Spacers[J].
The more triphenylene units on calix ..
AB - A novel hydrocarbon composed of three 9,10-dihydroanthracene units fused to the three pairs of β positions on a central triphenylene ring has been synthesised. The molecule defines two large cup-shaped cavities lined with π-electron system.
Thieme E-Journals - Synthesis / Abstract
N2 - A novel hydrocarbon composed of three 9,10-dihydroanthracene units fused to the three pairs of β positions on a central triphenylene ring has been synthesised. The molecule defines two large cup-shaped cavities lined with π-electron system.
purification and synthesis involving peptide coupling strategies
The synthesis and characterization of a shape-persistent triphenylene-butadiynylene macrocycle formed by intermolecular Glaser-coupling of two "half-rings" and also by intramolecular coupling of the appropriate open dimer, respectively, are described in detail. The investigation of the photophysics has revealed that - compared to its open dimer - the macrocycle is more conjugated in the ground state and less so in the excited state, a result of the diacetylene bending in the macrocycle due to its constrained topology. The macrocycle is decorated with flexible side groups that support its adsorption on highly oriented pyrolytic graphite (HOPG) where a concentration-dependence of the 2D-structure is observed by means of scanning tunnelling microscopy (STM). The flexible side groups also guarantee a high compound solubility even in nonpolar solvents (cyclohexane). However, solvophobic interactions lead to the formation of a tube-like superstructure, as revealed by dynamic light scattering, X-ray scattering and atomic force microscopy.
Synthesis of Water-Soluble Cyclophane Hexamers Having …
A novel hydrocarbon composed of three 9,10-dihydroanthracene units fused to the three pairs of β positions on a central triphenylene ring has been synthesised. The molecule defines two large cup-shaped cavities lined with π-electron system.