Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties
| Autor: | Bernhard Mayer, Dominik Urselmann, Konstantin Deilhof, Thomas Müller |
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| Rok vydání: | 2016 |
| Předmět: |
One-pot synthesis
010402 general chemistry Photochemistry DFT 01 natural sciences Full Research Paper microwave-assisted synthesis Fluorescence spectroscopy lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Thiophene ZINDO lcsh:Science Conformational isomerism multicomponent reactions 010405 organic chemistry Organic Chemistry C–C coupling palladium Fluorescence cyclic voltammetry 0104 chemical sciences Chemistry chemistry thiophenes copper lcsh:Q Absorption (chemistry) Cyclic voltammetry phenothiazines |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2055-2064 (2016) |
| ISSN: | 1860-5397 |
| DOI: | 10.3762/bjoc.12.194 |
| Popis: | The pseudo five-component Sonogashira–Glaser cyclization synthesis of symmetrically 2,5-diaryl-substituted thiophenes is excellently suited to access thienyl-bridged oligophenothiazines in a one-pot fashion. Three thienyl-bridged systems were intensively studied by UV–vis and fluorescence spectroscopy as well as by cyclic voltammetry. The oxidation proceeds with lower oxidation potentials and consistently reversible oxidations can be identified. The Stokes shifts are large and substantial fluorescence quantum yields can be measured. Computational chemistry indicates lowest energy conformers with sigmoidal and helical structure, similar to oligophenothiazines. TD-DFT and even semiempirical ZINDO calculations reproduce the trends of longest wavelengths absorption bands and allow the assignment of these transitions to possess largely charge-transfer character from the adjacent phenothiazinyl moieties to the central thienyl unit. |
| Databáze: | OpenAIRE |
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