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Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1)
Author(s) -
Szyszko Bartosz,
Rymut Paweł,
Matviyishyn Maksym,
Białońska Agata,
LatosGrażyński Lechosław
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202008518
Subject(s) - conformational isomerism , protonation , chemistry , kinetic control , stereochemistry , kinetic energy , computational chemistry , molecule , catalysis , organic chemistry , physics , quantum mechanics , ion
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.