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- Title
Reaction of Amines with 8-MethylthioBODIPY: Dramatic Optical and Laser Response to Amine Substitution.
- Authors
Esnal, Ixone; Urías ‐ Benavides, Arlette; Gómez ‐ Durán, C. F. Azael; Osorio ‐ Martínez, Carlos A.; García ‐ Moreno, Inmaculada; Costela, Angel; Bañuelos, Jorge; Epelde, Nerea; López Arbeloa, Iñigo; Hu, Rongrong; Zhong Tang, Ben; Peña ‐ Cabrera, Eduardo
- Abstract
A thorough study of the photophysical and laser properties of 8-aminoboron dipyrromethene dyes was undertaken to determine the role of amine substitution and spatial disposition on the properties of the dyes. It was found that the fluorescent and laser response varied significantly. Although primary amines give rise to highly fluorescent products at the blue edge of the visible region, secondary amines yield nonfluorescent analogues in polar media. The crystal structures of two analogues are reported and described. Steric hindrance and the higher electron-releasing ability of the amine favor the formation of a quenching charge-transfer state. Accordingly, boron dipyrromethene derivatives with primary amines exhibited laser emission with efficiencies of up to 44 %. Besides, the more efficient derivative was also the most photostable, leading to a significant improvement in the lasing performance with regard to previously reported 8-aminoboron dipyrromethene derivatives. An increase in the solvent polarity, and mainly the presence of tertiary cyclic amines, led to a dramatic decrease or even the loss of the laser action.
- Subjects
AMINES; DIPYRRINS; CRYSTAL structure; STERIC hindrance; BORON; CHARGE transfer; LASER photochemistry
- Publication
Chemistry - An Asian Journal, 2013, Vol 8, Issue 11, p2691
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201300760