Published June 27, 2021
| Version v1
Preprint
Open
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
Authors/Creators
- 1. Department of Inorganic Chemistry, Faculty of Natural Sciences, Comenius University, SK-84215 Bratislava, Slovakia
- 2. Faculty of Science, Charles University in Prague, Hlavova 2038/8, CZ-12843 Prague, Czech Republic
- 3. Department of Physics, University of Patras, GR-26504 Patras, Greece
- 4. Department of Inorganic Chemistry, Faculty of Natural Sciences, Comenius University, SK-84215 Bratislava, Slovakia; Laboratory for Advanced Materials, Comenius University Science Park, Ilkovičova 8, SK-84215 Bratislava, Slovakia
Description
Copper(II)-catalyzed C–H/C–H coupling of dipolar 2-H-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.
Files
OL 2021 - MS.pdf
Additional details
Funding
- European Commission
- LAMatCU - Establishing Laboratory of Advanced Materials at the Comenius University 810701
- European Commission
- TWOSENS - Towards Highly-Efficient Two-Photon Absorbing Sensitizers within a Confined Chromophore Space: From Computer-Aided Design to New Concepts and Applications 752285