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Synthesis of Stable [28π] m-Benzihexaphyrins (1.0.0.1.1.1).

Research paper by Sunit S Kumar, Mangalampalli M Ravikanth

Indexed on: 19 Oct '17Published on: 19 Oct '17Published in: Journal of Organic Chemistry



Abstract

Four new expanded [28π] m-benziporphyrins(1.0.0.1.1.1) were synthesized by [3+3] condensation of 10,10'-bis[(p-toly)hydroxymethyl]-1,3-bis(2-thienyl)benzenediol with various 16-tripyrranes such as 16-thiatripyrrane, 16-oxatripyrrane, 16-azatripyrrane and 16-selenatripyrrane under mild trifluoroacetic acid catalyzed reaction conditions. The macrocycles are freely soluble in common organic solvents and their identities were confirmed by HR-MS and detailed 1D and 2D NMR spectroscopy. The macrocycles showed one sharp Soret type band at ~500 nm and broad ill-defined Q-type band(s) in the region of 600-950 nm which supports their non-aromatic nature. Upon protonation, the macrocycles exhibited bathochromically shifted absorption bands with distinct change in the colour of the solutions. The preliminary studies carried out with one of the macrocycles indicated that the macrocycles have weak tendency to form coordination complexes.