Double helices of dissymmetrical α,α′-disubstituted tripyrrins?

Organic & Biomolecular Chemistry Pub Date: 2023-01-05 DOI: 10.1039/D2OB02125K

Abstract

Dissymmetrical α,α′-disubstituted tripyrrins have been prepared using a modified synthetic protocol. Tripyrrin 2a bearing 3,5-bis(trifluoromethyl)phenyl and 4-methoxyphenyl moieties showed an anti-type dimer arrangement in the solid state. In contrast, syn-type dimers were observed for tripyrrin 2b bearing 3,5-bis(trifluoromethyl)phenyl and 3,5-di-t-butylphenyl moieties. In addition, proton-exchange NH tautomerization was observed in 2b.

Graphical abstract: Double helices of dissymmetrical α,α′-disubstituted tripyrrins
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