RT Journal Article
T1 Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
A1 Fernandes Pais, Vania Cristina
A1 Neumann, Tristan
A1 Vayá, Ignacio
A1 Jiménez Molero, María Consuelo
A1 Ros, Abel
A1 Pischel, Uwe
AB 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. Laser-flash 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.
PB Beilstein-Institut
SN 1860-5397 (electrónico)
YR 2019
FD 2019
LK http://hdl.handle.net/10272/20863
UL http://hdl.handle.net/10272/20863
LA eng
NO Pais, V. F., Neumann, T., Vayá, I., Jiménez, M. C., Ros, A., & Pischel, U. (2019). Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence. Beilstein journal of organic chemistry, 15, 2612–2622. https://doi.org/10.3762/bjoc.15.254
NO Funding by the Spanish Ministry of Economy, Industry, andCompetitiveness (CTQ2014-54729-C2-1-P for U.P., CTQ2013-48164-C2-1-P and CTQ2013-48164-C2-2-P for A.R., Ramón yCajal contracts RYC-2013-12585 for A.R. and RYC-2015-17737 for I.V.), the Spanish Ministry of Science, Innovation,and Universities (CTQ2017-89832-P for U.P., CTQ2016-78875-P for M.C.J., and CTQ2017-89416-R for I.V.), the European Research and Development Fund, and the AndalusianGovernment (2012/FQM-2140 for U.P., 2009/FQM-4537 and2012/FQM-1078 for A.R) is gratefully acknowledged.
DS Repositorio Institucional de la Universidad de Huelva
RD 31 may 2026