A flexible approach towards substituted β- and γ-carbolines based on transition metal catalysed [2+2+2] cycloaddition reactions between functionalised yne-ynamides and methylcyanoformate is described. The versatility of this new reaction sequence is demonstrated by its application in the total synthesis of the marine natural product eudistomin U.

The first total synthesis of the potent antioxidant antiostatin A₁ is reported, where its key features rely on a chemo- and regioselective rhodium-catalysed crossed alkyne cyclotrimerisation reaction applying functionalised ynamides and a palladium-catalysed arylamidation reaction.

A set of methoxy-substituted diindolo[3,2-b:2′,3′-h]carbazoles has been synthesized by twofold Suzuki–Miyaura, Cadogan and N-alkylation reactions starting from N-hexyl-2,7-dibromo-3,6-dinitro carbazole. Microwave accelerated reactions ensure a rapid straightforward and step-ecomomic assembly of the diindolo[3,2-b:2′,3′-h]carbazole framework. Besides the parent diindolo[3,2-b:2′,3′-h]carbazole four new methoxy-group bearing derivatives were obtained and their molecular properties were investigated by thermal, photophysical and electrochemical means. Dichloromethane solutions of the diindolocarbazoles display with respect to the methoxy-group substitution pattern bright photoluminescences covering the blue to green spectra with quantum yields of ϕ_F = 0.20–0.27. Notably, the N,N,N-tri-n-hexyl-1,4,9,12-tetramethoxy diindolo[3,2-b:2′,3′-h]carbazole exhibits a remarkable aggregate induced excimer-type luminescence (^emλ_max = 562 nm, ^solidϕ_F = 0.14) in the solid state resulting in bright yellow light emission, whereas the parent non-substituted compound and the other methoxy-substituted derivatives show poor photoluminescence from the solid state. HOMO/LUMO energy levels were determined by means of electrochemical and photophysical methods and were compared to those obtained by computational methods using B3LYP/6-31G(d) DFT calculations with a Polarisable Continuum Model (CPCM) for the solvent CH₂Cl₂. Good linear correlation was observed between calculated and experimentally measured values, and the correlations were used to estimate experimental HOMO/LUMO energy values of still non-synthesized heteroatom extended heteroacenes.

A set of push–pull ynamides with up to four conjugated triple bonds has been synthesized and the molecular properties of these new carbon rods have been characterised showing effective intramolecular charge transfers and high values for the change of the electrical dipole moment after transition from the ground to the Franck–Condon excited state.

For the first time a fused polyaromatic compound is used for a single-layer single component WOLED.