Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane--an inverse photochromic system. (Photoactive cyclophanes 5).
The title compound, 4,13-bis[(1E,3E)-4-(9-anthracenyl)buta-1,3-dienyl][2.2]paracyclophane (2), prepared in 35% overall yield from [2.2]paracyclophane, absorbs light at lambda(max) = 400 nm with a tail down to 480 nm. By irradiation into this band, 2 generates a single photoproduct, 4, whose absorption maximum is situated at 306 nm. The starting material is recovered by irradiation at 306 nm or by heating. This 'inverse' photochromic system has a potential for optical information storage, compound 4 being stable in visible light, at ambient temperature.
Hopf
Henning
H
Institut für Organische Chemie, Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, Germany. h.hopf@tu-bs.de
Beck
Christian
C
Desvergne
Jean-Pierre
JP
Bouas-Laurent
Henri
H
Jones
Peter G
PG
Ernst
Ludger
L