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Fast Oxidative Cyclooligomerization towards Low‐ and High‐Symmetry Thiophene Macrocycles
Author(s) -
Maier Stefan K.,
Poluektov Georgiy,
Jester StefanS.,
Möller Heiko M.,
Höger Sigurd
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503211
Subject(s) - thiophene , oxidative phosphorylation , symmetry (geometry) , chemistry , photochemistry , combinatorial chemistry , organic chemistry , mathematics , biochemistry , geometry
Macrocycles with quaterthiophene subunits were obtained by cyclooligomerization by direct oxidative coupling of unsubstituted dithiophene moieties. The rings were closed with high selectivity by an α,β ′ ‐connection of the thiophenes as proven by NMR spectroscopy. The reaction of the precursor with terthiophene moieties yielded the symmetric α,α ′ ‐linked macrocycle in low yield together with various differently connected isomers. Blocking of the β‐position of the half‐rings yielded selectively the α,α ′ ‐linked macrocycle. Selected cyclothiophenes were investigated by scanning tunneling microscopy, which displayed the formation of highly ordered 2D crystalline monolayers.