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Biomedical subjects

Sigurd Höger

Publications and source records attributed to Sigurd Höger.

11 recordsLinked to original sources
PubMed2006

2D supramolecular structures of a shape-persistent macrocycle and co-deposition with fullerene on HOPG.

Two 2D supramolecular structures of macrocycle 1 and 1/C60 have been obtained on HOPG by self-assembly under ambient conditions and investigated by high-resolution STM. The monolayers of 1 are characterized by structures with perfect ordering over relatively large areas. In the case of 1/C60, the size of the macrocycle 1 and the presence of two individual bithiophene units per ring lead in the final superstructure to a 1:2 stoichiometry. The fullerenes are not trapped at the graphite surface inside the macrocyclic holes but are located around the periphery of the bithiophene units. This clearly shows that the donor-acceptor interaction between C60 and the electron-rich units of the ring is the dominant factor for the structure formation.

Journal Article↗
PubMed2006

Cationic shape-persistent macrocycles: the unexpected formation of a nano-size supramolecular dimer.

Shape-persistent macrocycles with a rigid pyridyl core and a flexible oligo-alkyl corona aggregate to some extent in nonpolar solvents to form large (tubular) aggregates. To increase the assembling tendency, the intraannular pyridyl groups of the macrocycles were alkylated. Unexpectedly, the quarternized macrocycles show no tendency at all to form tubular micellar-like structures but form well-defined dimers, as determined by X-ray and dynamic light scattering.

Journal Article↗
PubMed2004

Synthesis and characterization of monodisperse oligofluorenes.

An efficient synthesis of 9,9-bis(2-ethylhexyl)fluorene oligomers up to the heptamer is reported, with repetitive Suzuki and Yamamoto coupling reactions employed in the synthesis. The key steps for preparation of the essential intermediates include Pd-catalyzed transformation of aryl bromides to aryl boronic esters (Miyaura reaction) and the application of the much higher reactivity of aryl boronic esters over aryl bromides in the Pd-catalyzed cross-coupling reaction with aryl diazonium salts. Variation of the UV/Vis absorption and photoluminescence characteristics with chain length is reported. Moreover, glass transition and liquid-crystal characteristics of the oligomers are described and compared with those of the polymer.

Cross-Linking Reagents↗
PubMed2004

Shape-persistent macrocycles: from molecules to materials.

Shape-persistent macrocycles with an interior in the nanometer regime allow the attachment of (functional) side groups at defined positions at the ring. These side groups can have either a fixed orientation relative to the molecular backbone or they can adapt their orientation according to an external stimulus. The properties and applications of the compounds depend strongly on the orientation of these side groups. Macrocycles with intraannular or adaptable long alkyl groups display a new design principle for discotic liquid crystals. Macrocycles with extraannular (oligo)alkyl groups can be used for surface patterning in the nanometer regime and rings with extraannular oligostyryl groups are able to aggregate to supramolecular hollow polymer brushes.

Journal Article↗
PubMed2004

Shape-persistent macrocycles with intraannular polar groups: synthesis, liquid crystallinity, and 2D organization.

The synthesis of macrocycles with intraannular polar ester groups and extraannular oligo-alkyl groups is described. The compounds exhibit stable liquid crystalline phases showing fan-shaped textures under the polarizing microscope, typical for a columnar order of the molecules. X-ray powder diffraction data of the LC phase indicate that the unit cell contains two symmetry-related units, a feature pointing most probably to a restricted rotation of the macrocycles within a stack. The X-ray data were further supported by solid-state NMR experiments, showing that the rigid core of the compounds does not rotate with kHz or higher frequencies within the column in the LC phase. Apart from the organization of the molecules in the LC phase, the 2D organization of the macrocycles at the solvent-highly oriented pyrolytic graphite (HOPG) interface was investigated and showed that these compounds are capable of nanofunctionalizing the HOPG surface in the multinanometer regime.

Journal Article↗
PubMed2003

Synthesis and solid-state organization of coil-ring-coil block copolymers.

Shape-persistent macrocycles based on the phenyl-ethynyl-butadienyl backbone containing two extraannular hydroxyl groups were prepared by the oxidative coupling of the appropriate phenylethynyl oligomers. Carbodiimide-directed coupling with independently synthesized polystyrene carboxylic acid oligomers led to ABA coil-ring-coil block copolymers in which the central macrocycle serves as rigid and the polystyrene oligomers as flexible elements. Depending on the size of the coil blocks, these structures aggregate in cyclohexane into supramolecular hollow cylindrical brushes in which the rigid core is surrounded by the flexible matrix. However, in the solid state it is not possible to identify a morphology in which isolated channels based on aggregated macrocycles are embedded in a matrix of polystyrene. Detailed X-ray and electron diffraction studies on samples prepared from a solution in cyclohexane under equilibrium conditions show that the material adopts a lamellar morphology in the solid state in which columns of macrocycles are aggregated into layers which are separated by polystyrene.

Journal Article↗
PubMed2002

Solvent triggering between conformational states in amphiphilic shape-persistent macrocycles.

The amphiphilic shape-persistent macrocycle 1 containing four phenol-OH groups as polar side groups and four hexyloxy groups as nonpolar side groups in an adaptable arrangement was recrystallized from solvents of different polarity. X-ray crystallography reveals that the conformation of the macrocycle is solvent dependent such that in the pyridine solvate only two of the nonpolar side groups point outward while in the THF solvate all four of them point outward. Moreover, in the latter case the three-dimensional packing leads to the formation of a supramolecular channel structure with a large pore size.

Crystallography, X-Ray↗