Broman, Soren Lindbaek and Kushnir, Oleg and Rosenberg, Martin and Kadziola, Anders and Daub, Joerg and Nielsen, Mogens Brondsted (2015) Dihydroazulene/Vinylheptafulvene Photoswitch: Ultrafast Back Reaction Induced by Dihydronaphthalene Annulation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (19). pp. 4119-4130. ISSN 1434-193X, 1099-0690
Full text not available from this repository. (Request a copy)Abstract
The vinylheptafulvene (VHF) to dihydroazulene (DHA) electrocyclization is known to proceed from an s-cis conformation of VHF and cannot occur from the more stable s-trans conformation. Locking the VHF in the s-cis conformation by the introduction of a dihydronaphthalene (DHN) unit has been found to greatly enhance the speed of this reaction. Thus, the half-life was reduced by more than a factor of 150000 in cyclohexane and by a factor of approximately 950000 in ethanol. In addition, the characteristic absorption of the photoactive DHA isomer, now annulated to DHN, exhibited a desired redshift relative to the parent compound. Here, we present the synthesis and study of these DHN-DHA/VHFs, including a protocol for the incorporation of a pseudo-halide to enable the further functionalization of the molecule by metal-catalyzed cross-coupling reactions. For proof-of-concept, two different sulfur end-groups were incorporated as anchoring groups for potential molecular electronics applications.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | IONOTROPIC GLUTAMATE-RECEPTOR; RING-CLOSURE; LIGHT; DIHYDROAZULENE; MOLECULE; PHOTOCHROMISM; AZOBENZENE; SWITCHES; SUBSTITUENTS; CONDUCTANCE; Pericyclic reactions; Cross-coupling; Photochromism; Fused-ring systems |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 08 Jul 2019 13:33 |
| Last Modified: | 08 Jul 2019 13:33 |
| URI: | https://pred.uni-regensburg.de/id/eprint/5266 |
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