Quinoline-derived two-photon sensitive quadrupolar probes

Petra Dunkel (1) , Christine Tran (1) , Thibault Gallavardin (1) , Hamid Dhimane (1) , David Ogden (2) , Peter Dalko (1)

1 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques
2 LPC - UMR 8118 - Laboratoire de physiologie cérébrale

Quadrupolar probes derived from 8-dimethylamino-quinoline (8-DMAQ) having a pegylated fluorene core were prepared and studied under "one-photon" (λ=365 nm) and "two-photon" (TP) (λ=730 nm) irradiation conditions. Compound 1 a was identified as the most efficient probe by UV activation that showed sequential release of acetic acid as a model. Although the probe showed high two-photon absorption it stayed inert under femtosecond irradiation conditions. Fast and selective photolysis was observed, however, by using picosecond irradiation conditions with a remarkably high TP uncaging cross-section (δu =2.3 GM).

Keywords: absorption; chromophores; nonlinear optics; quinolines

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

Petra Dunkel, Christine Tran, Thibault Gallavardin, Hamid Dhimane, David Ogden, et al.. Quinoline-derived two-photon sensitive quadrupolar probes. Organic & Biomolecular Chemistry, 2014, 12 (48), pp.9899-9908. ⟨10.1039/C4OB01551G⟩. ⟨hal-02383445⟩