Synthesis of a dual clickable fullerene platform and construction of a dissymmetric BODIPY-[60]Fullerene-DistyrylBODIPY triad

The synthesis of a methanofullerene platform bearing on one side an alkyne and on the other a protected alkyne is reported. This clickable fullerene building block was functionalized by two distinct BODIPY azido derivatives using a 1st CuAAC/alkyne deprotection/2nd CuAAC, sequence, through either st...

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Bibliographic Details
Published in:	Tetrahedron Vol. 100; p. 132467
Main Authors:	Rabah, Jad, Yonkeu, Lyne, Wright, Karen, Vallée, Anne, Méallet-Renault, Rachel, Ha-Thi, Minh-Huong, Fatima, Anam, Clavier, Gilles, Fensterbank, Hélène, Allard, Emmanuel
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 05-11-2021 Elsevier
Subjects:	Boron dipyrromethenes Chemical Sciences Click chemistry CuAAC reaction Donor-acceptor systems Fullerene C60 CuAAC reaction Donor-acceptor systems Click chemistry Boron dipyrromethenes Fullerene C60
Online Access:	Get full text
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Summary:	The synthesis of a methanofullerene platform bearing on one side an alkyne and on the other a protected alkyne is reported. This clickable fullerene building block was functionalized by two distinct BODIPY azido derivatives using a 1st CuAAC/alkyne deprotection/2nd CuAAC, sequence, through either stepwise or one-pot processes in an efficient manner. The triad displays strong absorption from 300 to 700 nm. The strong fluorescence quenching observed for the two BODIPYs within the triad is probably due to photo-induced energy and/or electron transfer events. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2021.132467