Fluorescent aryl naphthalene dicarboximides with large Stokes shifts and strong solvatochromism controlled by dynamics and molecular geometry

Greiner, Robert; Schlücker, Thorben; Zgela, Dominik und Langhals, Heinz (25. Oktober 2016): Fluorescent aryl naphthalene dicarboximides with large Stokes shifts and strong solvatochromism controlled by dynamics and molecular geometry. In: Journal of Materials Chemistry C, Bd. 4, Nr. 47: S. 11244-11252

Abstract

A series of highly fluorescent 4-aryl substituted naphthalene dicarboximides were efficiently prepared via metal organic C–C-coupling reactions. The obtained push–pull fluorophores display a distinct positive solvatochromism of the fluorescence. These optical properties are shown to be significantly dependant on the molecular geometry. Corresponding to TICT, a twist between the donor and the acceptor moiety enhances the intramolecular charge transfer resulting in such pronounced solvatochromism. Complete orthogonalisation inhibits the fluorescence. An intentional skew arrangement leads to solvent-adjustable chromophores with high fluorescence quantum yields and Stokes shifts of more than 1.6 eV

• Dokumententyp: Zeitschriftenartikel
• Publikationsform: Publisher's Version
• Keywords: Recycling; Polymers; Fluorescence Deca;, Fluorescence Spectroscopy; Gaussian
• Fakultät: Chemie und Pharmazie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0959-9428
• Sprache: Englisch