Transamination of Zwitterionic Quinones with Polyamines: The Carbon Bridge Matters.

The one-pot transamination reactions on a zwitterionic benzoquinonemonoimine yield either a quinoxaline derivative or bis-zwitterionic macrocycles, depending on the number of carbon atoms bridging primary polyamines. These latter products, featuring two confined donor cavities, are the result of a [2 + 2] condensation without the need for template effect or high dilution conditions.

Two-step access to bis--perfluoroalkyl-corroles towards -perfluoroacyl-ABC-corroles.

A solventless and acid-catalyzed condensation of -perfluoroalkyl-dipyrromethanes with selected benzaldehydes was used to prepare ten different bilanes that were isolated before their oxidation into -AB-corroles bearing two -perfluoroalkyl groups. Macrocycles bearing long chains (CF or CF) are key precursors to afford ABC-corroles having a -acyl substituent when subjected to a mild and basic hydrolysis affecting one of the alkyl substituents.

Breaking Azacalix[4]arenes into Induline Derivatives.

Tetraamino-tetranitro-azacalixarene is at the crossroad of two different families of compounds depending on the conditions and the agent used to reduce the NO groups: (1) azacalixphyrin in neutral medium, or (2) phenazinium of type in acidic medium. The key role of the N-substituted amino functions at the periphery is highlighted by investigating octaaminoazacalixarene as a model compound, and by using the corresponding tetrahydroxy-tetranitro-azacalixarene as a precursor, which behaves differently.

A Strategy to Design Substituted Tetraamino-Phenazine Dyes and Access to an NIR-Absorbing Benzoquinonediimine-Fused Quinoxaline.

The straightforward access to N- or C-substituted dinitro-tetraamino-phenazines () is enabled in oxidative conditions via formation of two intermolecular C-N bonds from accessible 5-nitrobenzene-1,2,4-triamine precursors. The photophysical studies revealed green absorbing and orange-red emitting dyes, with enhanced fluorescence in the solid state. Further reduction of the nitro functions led to the isolation of a benzoquinonediimine-fused quinoxaline (), which undergoes diprotonation to form a dicationic coupled trimethine dye absorbing beyond 800 nm.