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

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

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-diiod...

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Bibliographic Details
Published in:Organic letters Vol. 23; no. 9; pp. 3460 - 3465
Main Authors: Nociarová, Jela, Osuský, Patrik, Rakovský, Erik, Georgiou, Dimitris, Polyzos, Ioannis, Fakis, Mihalis, Hrobárik, Peter
Format: Journal Article
Language:English
Published: United States American Chemical Society 07-05-2021
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Summary: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.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00893