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Synthesis and Photochemical Investigations of Tetrasubstituted Alkenes as Molecular Switches—The Effect of Substituents
Author(s) -
Tietze Lutz F.,
Düfert M. Alexander,
Hungerland Tim,
Oum Kawon,
Lenzer Thomas
Publication year - 2011
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.201003559
Subject(s) - stille reaction , chemistry , molecular switch , photochemistry , double bond , palladium , stereochemistry , medicinal chemistry , catalysis , molecule , polymer chemistry , organic chemistry
Molecular switches based on helical tetrasubstituted alkenes, substituted with either electron‐withdrawing (CF 3 , F, CN; 2 a – c , 3 a , c ) or ‐donating substituents (Me, OMe; 2 d , e ), have been synthesized from acyclic precursors 4 and 5 in a domino carbopalladation/Stille reaction. This palladium‐catalyzed process allowed the rapid assembly of two CC bonds, two six‐membered rings, and the tetrasubstituted double bond in a completely diastereoselective fashion. The electronic effects of the substituents on the overall switching process were investigated by alternating irradiation of two different wavelength regions. Although the substituents had only a small influence on the absorption maxima, drastic differences in the switching behavior were observed.