Kinetic versus Thermodynamic Control Over Multiple Conformations of Di-2,7-naphthihexaphyrin(1.1.1.1.1.1)

Bartosz Szyszko; Paweł Rymut; Maksym Matviyishyn; Agata Białońska; Lechosław Latos-Grażyński

doi:10.1002/anie.202008518

Kinetic versus Thermodynamic Control Over Multiple Conformations of Di-2,7-naphthihexaphyrin(1.1.1.1.1.1)

Angew Chem Int Ed Engl. 2020 Nov 2;59(45):20137-20146. doi: 10.1002/anie.202008518. Epub 2020 Aug 31.

Authors

Bartosz Szyszko¹, Paweł Rymut¹, Maksym Matviyishyn¹, Agata Białońska¹, Lechosław Latos-Grażyński¹

Affiliation

¹ Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383, Wrocław, Poland.

PMID: 33462869
DOI: 10.1002/anie.202008518

Abstract

Di-2,7-naphthihexaphyrin(1.1.1.1.1.1), a non-aromatic carba-analogue of the hexaphyrin(1.1.1.1.1.1), incorporating two built-in 2,7-naphthylene moieties was synthesized as two separate, conformationally locked stereoisomers. Both conformers followed complex protonation pathways involving structurally different species, which can be targeted under kinetic and thermodynamic control. The neutralization of the ultimate dicationic product, accessible from both stereoisomers of the free base, allowed to realize the complex conformational switching cycle involving six structurally different species.

Keywords: chirality; conformation analysis; macrocycles; porphyrinoids; supramolecular chemistry.

Abstract

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