Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 24, Pages 4157-4168Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800444
Keywords
C-C coupling; cyclocondensation; fluorescence; microwave reactions; multi-component reactions; pyrazoles
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Funding
- Fonds der Chemischen Industrie
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3,5-Disubstituted and 1,3,5-trisubstituted pyrazoles are readily synthesized from acyl chlorides, terminal alkynes, and hydrazines by a consecutive one-pot three-component Sonogashira coupling/Michael addition/cyclocondensation sequence in good to excellent yields. These pyrazoles are highly fluorescent, both in solution and in the solid state. Investigation of the electronic properties by UV/Vis and fluorescence spectroscopy and by DFT and ZINDO Cl computations reveal that the excited state is highly polar and allows fine-tuning of the absorption and emission properties. X-ray structure analyses of 3,5-disubstituted pyrazoles reveal self-organization by hydrogen bonding and pi-stacking. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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