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

Greiner, Robert; Schlücker, Thorben; Zgela, Dominik and Langhals, Heinz (25. October 2016): Fluorescent aryl naphthalene dicarboximides with large Stokes shifts and strong solvatochromism controlled by dynamics and molecular geometry. In: Journal of Materials Chemistry C, Vol. 4, No. 47: pp. 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

• Item Type: Journal article
• Form of publication: Publisher's Version
• Keywords: Recycling; Polymers; Fluorescence Deca;, Fluorescence Spectroscopy; Gaussian
• Faculties: Chemistry and Pharmacy
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0959-9428
• Language: English