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Functionalization of 3,5,8-Trichlorinated BODIPY Dyes.
- Source :
-
Journal of Organic Chemistry . 11/7/2014, Vol. 79 Issue 21, p10342-10352. 11p. - Publication Year :
- 2014
-
Abstract
- Catalytic hydrogenation of dibenzyl 5-dipyrroketone-2,9-dicarboxylates followed by decarboxylative iodination affords a 2,9-diiododipyrroketone which gives a 2,5,9-trichlorodipyrromethene hydrochloride after nucleophilic addition/elimination, with adventitious chloride to replace the two iodide groups. Treatment with BF3⋅Et2O gives a 3,5,8-trichloro-BODIPY that readily undergoes regioselective Stille coupling at the 8-position, or homo/mixed couplings at the 3,8- or 3,5- and 8-positions. Stepwise and controlled replacement of the 3,5- and 8-chlorine atoms using Stille reagents results in formation of a completely unsymmetrical trisubstituted BODIPY. Several examples of unsymmetrical BODIPYs were synthesized and characterized using this methodology. Structure features of new BODIPYs are discussed within the context of 14 new X-ray structures, and photophysical parameters of all new BODIPY compounds are reported and discussed. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CHLORINATION
*GOLD metallurgy
*DYES & dyeing
*COLOR
*CATALYTIC hydrogenation
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 79
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 99716284
- Full Text :
- https://doi.org/10.1021/jo501969z