Bodipy Dyes with Thienyl- and Dithienylthio-Substituents – Synthesis, Redox and Fluorescent Propertiesстатья
Статья опубликована в высокорейтинговом журнале
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 23 января 2018 г.
Аннотация:8-Phenyl- and 8-(4-nitrophenyl)-BODIPYs, thien-2-ylthio- and (2,2’-dithien-5-yl)-thio-substituted in 3,5-positions have been synthesized. 2-Thienylthio derivatives were obtained by two different sequences, i.e. via nucleophilic substitution in the corresponding 1,9-dichlorodipyrromethenes followed by the BODIPY formation and via the same reaction in 3,5-dichloro-BODIPY dyes. "Dipyrromethene route" has been shown to result in better overall yield. All dyes were characterized by UV-Vis, fluorescence spectroscopy and cyclic voltammetry (CVA) studies. UV-Vis spectra exhibited little dependence on the thiophene chain length. Thienylthia derivatives fluoresce with modest quantum yields, conversely, no fluorescence has been detected for their dithienylthio counterparts. 8-Phenyl-3,5-di(thien-2-ylthio)-BODIPY was characterized by X-ray crystallography, showing a layered arrangement of the molecules. Thienyl fragments of different molecules in the same layer form pairs alike H-aggregates, whereas BODIPYs moieties of different layers are arranged in J-aggregate type fashion. Solid fluorescence has been observed for these crystals that show broad emission from 600 nm to longer than 850 nm. CVA results correspond to those for known substituted BODIPYs, except unusually high current of the oxidation process of dithienyl derivatives with respect to the reduction one. This finding indicates oxidative film deposition