N-Phenylfluorubine: one functional dye - chromophor, fluorophor, electron-acceptor and moreElectronic supplementary information (ESI) available: Solvatochromism/titration/CV measurements, X-ray, results of DFT calculations and analytical data. CCDC 1497236 (3H22+·2Cl−). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6nj02544g

• Main Authors: Gampe, D. M, Schramm, S, Kaufmann, M, Görls, H, Beckert, R
• Format: Article
• Language: English
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c6nj02544g

We are presenting a new derivative of the fluorubine family which exhibits highly fluorescent activity. 5-Phenyl-dihydro[5,6,7,12,13,14]-hexaazapentacene was synthesized via two subsequent cyclization reactions starting from commercially available starting materials. Its properties were studied intensively via UV-vis and fluorescence spectroscopy, as well as cyclic voltammetry and quantum chemical calculations. Furthermore, we found a strong pH-sensitivity, which influences the photo- and electrochemical properties heavily. Thereby, it is possible to tune its properties from an electron-rich donor to a highly electron-deficient acceptor material. A new functional dye named: N -phenylfluorubine, is designed and characterized. It shows outstanding and tunable photo- and electrochemical properties.