Design of novel meso-CF3-BODIPY dyes with isoxazole substituents

The two approaches for the synthesis of meso-CF3 substituted BODIPY dyes bearing isoxazole substituents at the position 3 of boradiazaindacene core have been developed. The key stages of the approaches are cycloaddition of hydroxylamine to the triple bond of available ethynyldipyrromethanes (1) and...

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Bibliographic Details
Published in:Dyes and pigments 2018-05, Vol.152, p.14-18
Main Authors: Tomilin, D.N., Sobenina, L.N., Petrushenko, K.B., Ushakov, I.A., Trofimov, B.A.
Format: Article
Language:English
Subjects:
2,2,2-Trifluoro-1-(pyrrol-2-yl)-1-ethanols
BODIPY
Dipyrromethanes
Ethynylation
Ethynyldipyrromethanes
Isoxazole
meso-trifluoromethyl substituent
Pyrroles
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Summary:The two approaches for the synthesis of meso-CF3 substituted BODIPY dyes bearing isoxazole substituents at the position 3 of boradiazaindacene core have been developed. The key stages of the approaches are cycloaddition of hydroxylamine to the triple bond of available ethynyldipyrromethanes (1) and synthesis of isoxazoles from ethynylpyrrole and their further condensation with 2,2,2-trifluoro-1-(pyrrol-2-yl)-1-ethanols (2). The novel BODIPY dyes exhibit prospective optical features and fluorescence in the 611–646 nm with high (up to 0.94) quantum yield. Spectroscopic results have been rationalized with quantum mechanics calculation. •Two approaches to unsymmetrical isoxazole-containing meso-CF3 BODIPYs are described.•The key stage of regioselective formation of 3- or 5-isoxazolyl BODIPY is pH controlled.•Combination of biologically active units with BODIPY core is important for drug design.•Synthesized BODIPY dyes exhibit fluorescence in the 611–646 nm with high (up to 0.94) quantum yield.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2018.01.026