Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
[EN] Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic...
| Autores: | , , , , , |
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| Formato: | artículo |
| Fecha de publicación: | 2019 |
| País: | España |
| Recursos: | Universitat Politècnica de València (UPV) |
| Repositorio: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
| Idioma: | inglés |
| OAI Identifier: | oai:riunet.upv.es:10251/154390 |
| Acesso em linha: | https://riunet.upv.es/handle/10251/154390 |
| Access Level: | acceso abierto |
| Palavra-chave: | Arylisoquinolines Transient absorption spectroscoppy Anions Dyes Fluorescence Laser-flash photolysis Organoboron QUIMICA ORGANICA 03.- Garantizar una vida saludable y promover el bienestar para todos y todas en todas las edades |
| Resumo: | [EN] Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic acid esters by employing an Ir(I)-catalyzed reaction. The chromophores show dual emission behavior, where the long-wavelength emission band can reach maxima close to 600 nm in polar solvents. The fluorescence quantum yields of the dyes are generally in the range of 0.2¿0.4, reaching in some cases values as high as 0.5¿0.6. Laserflash photolysis provided evidence for the existence of excited triplet states. The dyes form fluoroboronate complexes with fluoride anions, leading to the observation of the quenching of the long-wavelength emission band and ratiometric response by the build-up of a hypsochromically shifted emission signal. |
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