Synthesis and photodimerisation of tetrabenzo[ab,f,jk,o][18]annulenes

Abstract The tetrabenzo[ab,f,jk,o][18]annulenes 7a,b, generated in a 5-step synthesis, show photodimerisation and -oligomerisation reactions in the solid state and in solution. The state of aggregation determines the reaction route. Whereas the cyclodimer 8a has a simple cyclobutane structure, the dimer 8b is a highly symmetrical cyclophane.

ChemInform Abstract: Synthesis and Photodimerization of Tetrabenzo[ab,f,jk,o][18]annulenes.

ChemInform Abstract: Synthesis of Areno-Condensed [24]Annulenes.

[24]Annulenes condensed with three phenanthrene units (11a−d) or with three chrysene ring systems (22) were prepared by multi-step syntheses. The cyclic condensation reaction in the final step led to highly symmetrical compounds. Long flexible alkoxy groups attached to the periphery enhance the solubility and give rise to a strong aggregation of the molecules which was observed in solution by NMR and fluorescence excitation spectroscopy, and in the pure state by the detection of liquid crystalline phases in differential scanning calorimetry and polarization microscopy.

ChemInform Abstract: Synthesis of Tripyreno[2,3,4,-abc:2,3,4-ghi:2,3,4-mno][18]annulenes.

The title compounds were prepared in a multi-step synthesis in which primarily the pyrene building blocks were formed (1,2 11a,b). The final reaction step 11a,b 12a,b consisted of a threefold trans selective cyclocondensation process that generated the central 18-membered ring. Hexyloxy or dodecyloxy sidechains attached on the periphery led to the formation of liquid crystalline phases.

Photoreactive Liquid Crystals in the Series of Dendritic and Cyclic Stilbenoid Compounds

The dendrimers 1 and 2 and the areno-condensed annulenes 3 and 4 represent new mesogens for the generation of discotic mesophases. The stilbenoid building blocks of these compounds provide the molecular basis for interesting photochemical and photophysical effects like dimerisation, oligomerisation or the formation of charge carriers.

Synthesis of Areno-Condensed [24]Annulenes

[24]Annulenes condensed with three phenanthrene units (11a−d) or with three chrysene ring systems (22) were prepared by multi-step syntheses. The cyclic condensation reaction in the final step led to highly symmetrical compounds. Long flexible alkoxy groups attached to the periphery enhance the solubility and give rise to a strong aggregation of the molecules which was observed in solution by NMR and fluorescence excitation spectroscopy, and in the pure state by the detection of liquid crystalline phases in differential scanning calorimetry and polarization microscopy.

Synthesis of Tripyreno[2,3,4-abc: 2,3,4-ghi: 2,3,4-mno][18]annulenes

The title compounds were prepared in a multi-step synthesis in which primarily the pyrene building blocks were formed (1,2 11a,b). The final reaction step 11a,b 12a,b consisted of a threefold trans selective cyclocondensation process that generated the central 18-membered ring. Hexyloxy or dodecyloxy sidechains attached on the periphery led to the formation of liquid crystalline phases.

Areno-Condensed 1,7,13-Triaza[18]annulenes

The 1,7,13-triaza[18]annulenes 9a−c were prepared by multi-step processes in which the final step consisted of a threefold cyclic condensation reaction of the Schiff bases 8a−c. Due to the length of the nine peripheral alkoxy chains, discotic liquid crystalline phases were obtained for 9b,c. The three nitrogen atoms in the central 18-membered ring not only permit protonation, but they can also serve for the complexation of NH4+ ions. The compounds 9a−c are highly photosensitive and exhibit crosslinking reactions on irradiation.

Aggregation and Photodimerization of Areno-Condensed Annulenes