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1 article(s) from Beck, Christian

Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5)

Henning Hopf,
Christian Beck,
Jean-Pierre Desvergne,
Henri Bouas-Laurent,
Peter G. Jones and
Ludger Ernst

Beilstein J. Org. Chem. 2009, 5, No. 20, doi:10.3762/bjoc.5.20

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Figure 1: Schematic representation of a photochromic system. The reverse reaction can be a photochemical or t...

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Figure 2: Photochromic reaction of pseudo-gem disubstituted tetraene [2.2]cyclophane 1 in acetonitrile, conc....

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Figure 3: Molecular structure of 4,13-bis[(1E,3E)-4-(9-anthracenyl)-buta-1,3-dienyl][2.2]paracyclophane (2).

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Scheme 1: Preparation of 2 (last step), using the Wittig reaction. The preparation of 3 has been described in...

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Figure 4: Molecular structure of 2 in the crystal. Radii are arbitrary; only selected H atoms are shown.

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Figure 5: Projection of the molecular structure of 2 exhibiting the closest internuclear distances (distances...

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Figure 6: Electronic absorption spectra of 2 (conc. ca 10⁻⁴ M) in MCH (full line) and CH₃CN (dotted line) at ...

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Figure 7: Irradiation of 2 (2.6 × 10⁻⁵ M) in CH₃CN at 400 nm at 20 °C. The spectra were recorded at various t...

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Figure 8: Irradiation at 306 nm of the photoproduct 4 obtained at 400 nm in the same setup; the spectra were ...

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Figure 9: Reversibility of the formation of the photoproduct 4 at 400 nm (40 min) and photodissociation of 4 ...

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Figure 10: ¹H NMR spectra (400 MHz, CDCl3). A: Compound 2, B: Compound 4.

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Figure 11: Proposed structure of 4 (1,4 : 2′,3′-cycloadduct).

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Published 07 May 2009

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