On the Physicochemical Properties of Pyridohelicenes

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TitreOn the Physicochemical Properties of Pyridohelicenes
Type de publicationJournal Article
Year of Publication2014
AuteursChocholousova JVacek, Vacek J, Andronova A, Misek J, Songis O, Samal M, Stara IG, Meyer M, Bourdillon M, Pospisil L, Stary I
JournalCHEMISTRY-A EUROPEAN JOURNAL
Volume20
Pagination877-893
Date PublishedJAN 13
Type of ArticleArticle
ISSN0947-6539
Mots-clésbasicity, chirality, cyclic voltammetry, Density functional calculations, helical structures, helicenes
Résumé

A comprehensive study on the physicochemical properties of a series of mono- and diaza[5]helicenes as well as mono- and diaza[6]helicenes is reported. Through the use of both computational and experimental methods, these helically chiral pyridohelicenes with the nitrogen atom(s) in various positions are characterised according to their inversion barriers, protonation constants and redox potentials. By using DFT calculations, kinetic measurements, UV/Vis titrations, cyclic voltammetry and EPR spectroscopy, a self-contained picture of their behaviour under conventional treatment by heat, acids and oxidising/reducing agents is provided.

DOI10.1002/chem.201204410