Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 14333-14355Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00846
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Funding
- DFG [EXC 2122, 390833453]
- European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme [714429]
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The synthesis and emission behavior of minimalistic 2-(oxazolinyl)-phenols and their derivatives were investigated, revealing that the position and nature of substituents can affect emission efficiency and characteristics. Single-crystal analysis showed unique packing motifs and an isolation of ESIPT-based fluorophores in the keto form.
Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.
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