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 absorpti...

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Published inBeilstein journal of organic chemistry Vol. 5; no. 1; p. 20
Main Authors Hopf, Henning, Beck, Christian, Desvergne, Jean-Pierre, Bouas-Laurent, Henri, Jones, Peter G, Ernst, Ludger
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 07.05.2009
Subjects
anthracenes
Chemistry
cyclophanes
Full Research Paper
inverse photochromism
photocycloaddition
photocycloaddition
inverse photochromism
anthracenes
cyclophanes
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Summary: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.
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.5.20