First synthesis and electronic properties of cyano(oligo)phenothiazines

Blue to green daylight fluorescent and electroactive (oligo)phenothiazinyl nitriles can be obtained in good to very good yields via Beller cyanation either under conductive or dielectric heating. (Oligo)phenothiazinyl nitriles were synthesized in good to very good yields from bromo (oligo)phenothiaz...

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Bibliographic Details
Published in:Tetrahedron letters 2008-05, Vol.49 (20), p.3300-3303
Main Authors: Franz, Adam W., Popa, Larisa N., Müller, Thomas J.J.
Format: Article
Language:English
Subjects:
Cyanation
Cyclovoltammetry
Fluorescence
Microwave chemistry
Palladium
Phenothiazine
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Summary:Blue to green daylight fluorescent and electroactive (oligo)phenothiazinyl nitriles can be obtained in good to very good yields via Beller cyanation either under conductive or dielectric heating. (Oligo)phenothiazinyl nitriles were synthesized in good to very good yields from bromo (oligo)phenothiazines via the Beller cyanation protocol either under conductive or under dielectric heating using NMP as a solvent. Their electronic properties were determined by absorption and emission spectroscopy and cyclic voltammetry. Cyano(oligo)phenothiazines display large Stokes-shifts (5800–8300 cm −1) and substantial quantum yields (11–27%). Their reversible oxidation potentials are considerably shifted anodically due to the electron-withdrawing character of the cyano group.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.03.071