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Oxidative Cyclodehydrogenation Reactions with Tetraarylporphyrins
Author(s) -
Martin Max M.,
Oleszak Christoph,
Hampel Frank,
Jux Norbert
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001174
Subject(s) - porphyrin , chemistry , reactivity (psychology) , aryl , photochemistry , redox , spectroscopy , solid state , combinatorial chemistry , organic chemistry , medicine , alkyl , alternative medicine , physics , pathology , quantum mechanics
The extension of the aromatic π‐system of porphyrins is a powerful method to alter their optoelectronic properties. Herein, aryl substituents were fused to porphyrin cores by Scholl oxidation reactions that selectively produced mono‐ and doubly‐fused porphyrins in yields of up to 69 %. Several different aryl substituents attached to the porphyrin were investigated with respect to their reactivity under Scholl conditions. The fused products were fully characterized, i.e., by UV/Vis absorption spectroscopy, which showed drastic changes in the electronic features. Insight into the solid‐state behavior was obtained by X‐ray crystallography. Our approach represents a novel option for the late‐stage functionalization of porphyrin‐based compounds.