Published April 18, 2021
| Version v1
Preprint
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Direct Iodination of Electron-Deficient Benzothiazoles: Rapid Access to Two-Photon Absorbing Fluorophores with Quadrupolar D-π-A-π-D Architecture and Tunable Heteroaromatic Core
Creators
- 1. Department of Inorganic Chemistry, Faculty of Natural Sciences, Comenius University, SK-84215 Bratislava, Slovakia
- 2. Department of Physics, University of Patras, GR-26504 Patras, Greece
- 3. Department of Inorganic Chemistry & Laboratory for Advanced Materials, Faculty of Natural Sciences, Comenius University, SK-84215 Bratislava, Slovakia
Description
Direct iodination of benzothiazoles under strong oxidative/acidic conditions leads to a mixture of iodinated heteroarenes with 1–2 major components, which are easily separable and which structures depend on the I2 equivalents used. Among the unexpected but dominant products were identified 4,7-diiodobenzothiazoles with a rare substitution pattern for SEAr reactions of this scaffold. These were employed in the synthesis of 4,7-bis(triarylamine-ethynyl)benzothiazoles — a new class of highly efficient quasi-quadrupolar fluorophores displaying large two-photon absorption cross sections (540–1374 GM) in the near-infrared region.
Files
Org Lett 2021 - preprint.pdf
Additional details
Funding
- 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
- European Commission