π-Expanded and N-Doped Fluoranthenes.

Novel π-expanded and N-doped fluoranthenes were synthesized and thoroughly investigated. These eight unsubstituted compounds are obtained in a multistep synthesis with CH activation as the last key reaction step. The structures vary in their position of π-expansion on the fluoranthene scaffold and the location of the pyridinic nitrogen atom.

Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines.

Three bis- or tris-brominated 2-trifluoromethylquinolines have been successfully applied in palladium-catalysed Sonogashira reactions, leading to several examples of alkynylated quinolines in good to excellent yields. Optical properties of selected products have been studied by steady state absorption and fluorescence spectroscopy which give insights of the influence of the substitution pattern and of the type of substituents on the optical properties.

Synthesis and Properties of Diphenylbenzo[j]naphtho[2,1,8-def][2,7]phenanthrolines.

A series of hitherto unknown 5,14-diphenylbenzo[j]naphtho[2,1,8-def][2,7]phenanthrolines, containing a 5-azatetracene and a 2-azapyrene subunit, were prepared by combination of Pd-catalyzed cross-coupling reactions with a one-pot Povarov/cycloisomerization reaction. In the final key step four new bonds are formed in one step. The synthetic approach allows for a high degree of diversification of the heterocyclic core structure.