| Abstract
| - Tetraphenoxy-substituted diazadibenzoperylenes 5a,b were synthesized from tetrachloroperylenetetracarboxylic acid bisanhydride 1 through imidization with benzylamine, nucleophilic displacementof the four chlorine atoms by phenolates, carbonyl group reduction by LiAlH4/AlCl3, and subsequentPd/C-promoted debenzylation−dehydrogenation. The structural properties of these extendeddiazaarenes are discussed on the basis of a X-ray crystal structure of the N,N‘-dibutylateddiazadibenzoperylenium dication 6, which revealed a 25° twist of the central six-membered ringleading to an atropisomeric π-conjugated backbone. The chromophoric systems of 5 and 6 werecharacterized by optical absorption and fluorescence spectroscopy, which revealed an intensefluorescence with a quantum yield of 75% for 5 and 50% for 6. Cyclic voltammetry showed reversibleoxidation and reduction waves for 6, whereas the oxidation of 5 afforded the irreversible depositionof a conductive film on the electrode surface. Finally, the potential use of ligands 5 in supramolecularchemistry has been evaluated by complexation experiments with carboxylic acids and zinctetraphenylporphyrin (ZnTPP).
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