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Redox‐Controlled Dihydroazulene‐Vinylheptafulvene Photoswitch Incorporating Tetrathiafulvalene
Author(s) -
Petersen Michael Åxman,
Andersson Asbjørn Sune,
Kilså Kristine,
Nielsen Mogens Brøndsted
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.200900041
Subject(s) - chemistry , tetrathiafulvalene , photoswitch , azulene , redox , conjugate , photochemistry , radical ion , organic chemistry , molecule , ion , mathematical analysis , mathematics
A derivative of dihydroazulene (DHA) incorporating the redox‐active unit tetrathiafulvalene (TTF) was prepared and investigated for its ability to undergo light‐induced conversion to the vinylheptafulvene (VHF) isomer. The absorption properties of the oxidized species were investigated by spectroelectrochemistry. Photoswitching was investigated as a function of the redox‐state of the TTF unit, i.e., as neutral or as radical cation, and it was found that photoswitching occurred more than twice as efficiently for the neutral species as for the radical cation species, while the thermal back reaction was unaffected. In addition, we have found that the TTF–DHA conjugate is readily converted to an azulene–TTF donor–acceptor conjugate upon treatment with strong base.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)