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Greiner, Robert; Schlücker, Thorben; Zgela, Dominik; Langhals, Heinz ORCID: 0000-0002-8038-4547 (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


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