Fluorophores for Excited-State Intramolecular Proton Transfer by an Yttrium Triflate Catalyzed Reaction of Isocyanides with Thiocarboxylic Acids |
| |
| Authors: | Dr Shuo Tong Shun Zhao Dr Qing He Dr Qian Wang Prof Dr Mei-Xiang Wang Prof Dr Jieping Zhu |
| |
| Institution: | 1. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland;2. Department of Chemistry, The University of Texas at Austin, Austin, TX, 78712-1224 USA;3. Key Laboratory of Bioorganic Phosphorous and Chemical Biology (Ministry of Education), Tsinghua University, Beijing, 100084 China |
| |
| Abstract: | Discovery of new chemical reactivity of a given functional group can often result in innovative synthesis of important chemical entities that possess unprecedented properties. We designed and developed a one-step synthesis of 5-amino-4-carboxamidothiazoles 1 by an yttrium-triflate-catalyzed reaction of thiocarboxylic acids 2 with isocyanides 3 . In this reaction, both reactants 2 and 3 deviated from their normal reactivities because of metal coordination. The resulting heterocycles are novel prototypical structures for the double ESIPT process. Some of them were excited by visible light irradiation and emitted fluorescence at the NIR region with large Stokes shift, high quantum yield, and strong solvatochromism. |
| |
| Keywords: | Fluoreszenz Homogene Katalyse Isocyanide Mehrkomponentenreaktionen Wasserstoffbrücken |
|
|
