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Synthesis and Property Studies of Cyclotrisazobenzenes
Author(s) -
Reuter Raphael,
Hostettler Nik,
Neuburger Markus,
Wegner Hermann A.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900861
Subject(s) - photoisomerization , chemistry , azobenzene , isomerization , photochromism , yield (engineering) , solid state , irradiation , photochemistry , stereochemistry , organic chemistry , catalysis , molecule , materials science , physics , nuclear physics , metallurgy
Azobenzenophanes are fascinating macrocycles, which are of special interest due to their unique photochromic behavior. Cyclotrisazobenzenes 2 (R = H, Br, t Bu) were prepared to probe how much strain the photoisomerization of the azobenzene motive can tolerate. The macrocycles were synthesized in an overall yield of 10–20 % from ortho ‐phenylenediamine ( 6 ). Solid‐state structures of cyclotrisazobenzenes 2a and 2b were obtained. Irradiation under various conditions did not induce any isomerization.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)