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 λmax = 400 nm with a tail down to 480 nm. By irradiation into this band, 2 generates a single photoproduct, 4, whose absorption maxi...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2009-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.5.20 |
| _version_ | 1818846391303143424 |
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| author | Henning Hopf Christian Beck Jean-Pierre Desvergne Henri Bouas-Laurent Peter G. Jones Ludger Ernst |
| author_facet | Henning Hopf Christian Beck Jean-Pierre Desvergne Henri Bouas-Laurent Peter G. Jones Ludger Ernst |
| author_sort | Henning Hopf |
| collection | DOAJ |
| description | 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 λmax = 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. |
| first_indexed | 2024-12-19T05:44:48Z |
| format | Article |
| id | doaj.art-c216927985fd4036a3b7d3cd7e4f63d4 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T05:44:48Z |
| publishDate | 2009-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-c216927985fd4036a3b7d3cd7e4f63d42022-12-21T20:33:54ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972009-05-01512010.3762/bjoc.5.201860-5397-5-20Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5)Henning Hopf0Christian Beck1Jean-Pierre Desvergne2Henri Bouas-Laurent3Peter G. Jones4Ludger Ernst5Institut für Organische Chemie, Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, GermanyInstitut für Organische Chemie, Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, GermanyISM, CNRS UMR 5255, Université Bordeaux 1, F-33405 Talence Cedex, FranceISM, CNRS UMR 5255, Université Bordeaux 1, F-33405 Talence Cedex, FranceInstitut für Anorganische Chemie, Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, GermanyNMR-Laboratorium der Chemischen Institute der Technischen Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, GermanyThe 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 λmax = 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.https://doi.org/10.3762/bjoc.5.20anthracenescyclophanesinverse photochromismphotocycloaddition |
| spellingShingle | Henning Hopf Christian Beck Jean-Pierre Desvergne Henri Bouas-Laurent Peter G. Jones Ludger Ernst Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5) Beilstein Journal of Organic Chemistry anthracenes cyclophanes inverse photochromism photocycloaddition |
| title | Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5) |
| title_full | Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5) |
| title_fullStr | Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5) |
| title_full_unstemmed | Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5) |
| title_short | Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5) |
| title_sort | reversible intramolecular photocycloaddition of a bis 9 anthrylbutadienyl paracyclophane an inverse photochromic system photoactive cyclophanes 5 |
| topic | anthracenes cyclophanes inverse photochromism photocycloaddition |
| url | https://doi.org/10.3762/bjoc.5.20 |
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