Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 17, Pages 7512-7525Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301300b
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- CNRS
- Ministere de l'Enseignement Superieur et de la Recherche
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We report the synthesis of BODIPYs with unsubstituted 1,7,8-positions and their dimerization by oxidative coupling with phenyliodine(III)-bis(trifluoroacetate) (PIFA). This dimerization was achieved for BODIPYs substituted in the 3,5-positions with either methyl or thienyl groups. The position and the type of the linkage in the resulting dimers depended on the nature of the substituent. The 3,5-dimethyl-BODIPY dyes were linked either via direct 1,1'-pyrrole pyrrole coupling or via a 1,3'-methylene bridge. The 3,5-dithienyl-BODIPY dyes provided, in excellent yields, unique compounds linked exclusively via the alpha-thienyl positions. All dyes were unreactive in the 8-position. Electrochemical and spectroscopic measurements on the monomers and dimers provided evidence of interactions between the two halves of the dimers. Thus, oxidation and reduction potentials were split by up to 210 mV, and modest excitonic coupling and an internal charge transfer were observed in some cases.
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