Access to 2,6-Dipropargylated BODIPYs as “Clickable” Congeners of Pyrromethene-567 Dye: Photostability and Synthetic Versatility

Hitherto unreported 2,6-dipropargyl-1,3,5,7-tetramethyl BODIPYs can be efficiently prepared by a Nicholas reaction/decomplexation protocol from 1,3,5,7-tetramethyl BODIPYs. The title compounds, which improve the BODIPY photostability by retaining their inherent photophysical and photochemical proper...

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Veröffentlicht in:Organic letters 2021-09, Vol.23 (17), p.6801-6806
Hauptverfasser: Uriel, Clara, Gómez, Ana M, García Martínez de la Hidalga, Enrique, Bañuelos, Jorge, Garcia-Moreno, Inmaculada, López, J. Cristobal
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Sprache:eng
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Zusammenfassung:Hitherto unreported 2,6-dipropargyl-1,3,5,7-tetramethyl BODIPYs can be efficiently prepared by a Nicholas reaction/decomplexation protocol from 1,3,5,7-tetramethyl BODIPYs. The title compounds, which improve the BODIPY photostability by retaining their inherent photophysical and photochemical properties, can be engaged in efficient copper­(I)-catalyzed azide–alkyne cycloaddition (CuAAC) “click-type” reactions with azido derivatives to provide all-BODIPY-triads or conjugated BODIPYs.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02380