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Modular Synthesis, Orthogonal Post‐Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes
Author(s) -
Torricelli Franck,
Bosson Johann,
Besnard Céline,
Chekini Mahshid,
Bürgi Thomas,
Lacour Jérôme
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201208926
Subject(s) - cationic polymerization , electrophile , surface modification , condensation , nucleophile , combinatorial chemistry , chemistry , absorption (acoustics) , enantiomer , coupling (piping) , polymer chemistry , materials science , organic chemistry , physics , catalysis , composite material , thermodynamics , metallurgy
Pick and choose : Novel cationic diaza‐, azaoxo‐, and dioxo[6]helicenes are readily prepared and functionalized selectively by orthogonal aromatic electrophilic and vicarious nucleophilic substitutions (see scheme). Reductions, cross‐coupling, or condensation reactions introduce additional diversity and allow tuning of the absorption properties up to the near‐infrared region. The diaza salts can be resolved into single enantiomers.