2009年
Functionalization of Boron Dipyrrin (BODIPY) Dyes through Iridium and Rhodium Catalysis: A Complementary Approach to alpha- and beta-Substituted BODIPYs
CHEMISTRY-A EUROPEAN JOURNAL
- ,
- ,
- ,
- 巻
- 15
- 号
- 24
- 開始ページ
- 5942
- 終了ページ
- 5949
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/chem.200802541
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
Iridium-catalyzed direct borylation has been applied to meso-substituted dipyrromethane and boron dipyrrin (BODIPY) dyes. Borylation is highly regioselective and complementary: it occurs exclusively at the alpha position for meso-mesityldipyrromethane and at the beta positions for meso-mesityl BODIPY dye. This regioselective borylation enables a variety of alpha- and beta-substituted BODIPY dyes to be synthesized. Introduction of alpha,beta-enoate and alpha,beta,gamma,delta-dienoate functions into BODIPY dyes at the alpha or beta positions was achieved by rhodium-catalyzed Heck-type addition of the borylated compounds to acrylate and 2,4-pentadienoate esters. This functionalization has a significant effect on the electronic properties of BODIPY dyes, as seen in substantial redshift of the absorption and emission spectra. Comparative studies showed that the alpha- and beta-substituted series of BODIPY dyes show substantially different photophysical properties, and thus the importance of the position to be functionalized is highlighted.
- リンク情報
- ID情報
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- DOI : 10.1002/chem.200802541
- ISSN : 0947-6539
- eISSN : 1521-3765
- ORCIDのPut Code : 12623720
- SCOPUS ID : 66349103604
- Web of Science ID : WOS:000267278900012