Oxidative C–H Homocoupling of Push–Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption
Patrik Osuský, Jela Nociarová, Maroš Smolíček, Róbert Gyepes, Dimitris Georgiou, Ioannis Polyzos, Mihalis Fakis, Peter Hrobárik
Abstract
-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2'-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2'-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.
Topics & Concepts
TriphenylamineAbsorption (acoustics)FluorescenceTwo-photon absorptionChemistryPhotochemistryAtom (system on chip)BipyridineCombinatorial chemistryMaterials scienceCrystallographyOpticsPhysicsCrystal structureEmbedded systemLaserComputer scienceComposite materialNonlinear Optical Materials StudiesPhotochromic and Fluorescence ChemistryNonlinear Optical Materials Research