E‐Diazocine in Chemical Education: Synthesis, Structure, Photochromism and Thermal Stability. Issue 1 (2nd November 2017)

• Record Type: Journal Article
• Authors: Krämer, René; Nöthling, Nils; Lehmann, Christian W.; Mohr, Fabian; Tausch, Michael W.
• Is Part Of: ChemPhotoChem. Volume 2:Issue 1(2018)
• Page Start: 6
• Page End: 11
• Publication Date: 2017-11-02
• Subjects: chemical education -- isomerization -- molecular switches -- reaction pathways -- X-ray crystallography; Photochemistry -- Periodicals; Periodicals; Electronic journals; 541.35
• DOI: 10.1002/cptc.201700124
• Languages: English
• ISSNs: 2367-0932

Abstract

Abstract: Z ‐diazocine, synthesized as described by Tellkamp, 1 has been photochemically converted into E ‐diazocine by irradiation of its solution at λ =365 nm. After purification, single crystals of E ‐diazocine were obtained by recrystallization at −18 °C from n ‐pentane. The title compound was characterized by NMR spectroscopy and X‐ray crystallography. For its thermal isomerization into the more stable Z ‐isomer, the thermal half‐life was determined by UV/Vis absorption studies. Furthermore, the photochemical behaviour of the compound in the solid state has been investigated. Abstract : Seeing is believing : The photochemical conversion of Z ‐diazocine (left, see picture) into E ‐diazocine (right) as a straightforward classroom demonstration of E / Z isomerization and photoswitching is presented. E ‐diazocine was characterized by NMR spectroscopy and X‐ray crystallography. The thermal half‐life of the compound was determined by UV/Vis absorption studies and its photochemical behaviour in the solid state was investigated.