Sequential palladium catalyzed coupling-cyclocondensation-coupling (C3) four-component synthesis of intensively blue luminescent biarylsubstituted pyrazolesElectronic supplementary information (ESI) available: Synthesis of reference compound 9, 1H and 13C NMR spectra, UV/Vis and fluorescence spectra of compounds 5, 6, 7, 8, and 9; computed xyz-coordinates of the S0 state of the pyrazoles 5c, 6d, and 8b, computed UV/Vis spectra of TD-DFT calculated structures of 5c, 6d, and 8b, computed xyz-coord
1-, 3-, and 5-Biarylsubstituted pyrazoles can be efficiently prepared by a microwave-assisted consecutive four-component synthesis based upon a sequential Pd-catalyzed coupling-condensation-coupling (C 3 ), a one-pot sequence which concatenates Sonogashira alkynylation and Suzuki arylation intercept...
Gespeichert in:
Hauptverfasser: | , , , , , |
---|---|
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | 1-, 3-, and 5-Biarylsubstituted pyrazoles can be efficiently prepared by a microwave-assisted consecutive four-component synthesis based upon a sequential Pd-catalyzed coupling-condensation-coupling (C
3
), a one-pot sequence which concatenates Sonogashira alkynylation and Suzuki arylation intercepted by pyrazole forming cyclocondensation of the ynone intermediate. This diversity-oriented approach enables tailoring, fine-tuning and optimization of absorption and emission properties towards high fluorescence quantum yields in solution up to
Φ
f
= 0.97. The increased luminescence intensity stemming from biaryl substitution can be rationalized by ground and excited state computations on the DFT level of theory, which nicely reproduce the experimental data of absorption and emission.
Highly blue-fluorescent 1-, 3-, and 5-biarylsubstituted pyrazoles can be efficiently prepared by a MW-assisted consecutive four-component synthesis based upon a sequential Pd-catalyzed Sonogashira coupling-condensation-Suzuki coupling (C
3
) process. |
---|---|
ISSN: | 2046-2069 |
DOI: | 10.1039/c5ra03104d |