Synthesis general. Solvents were obtained from SDS and are synthetic grade. Reagents were bought form Aldrich Chemical Co. or AlfaAesar Chemical Co. NMR spectra were measured from CDCl 3 solutions of the samples using a Bruker DPX 400 spectrometer or a JEOL ECS400 spectrometer, with TMS as an internal standard. Syntheses of compounds 5 24b , 6, 10 and 14 31 have been published elsewhere. Scheme S1. Synthesis of ketoximes 10-13 from [2.2]paracyclophane. General procedure for the synthesis of ketones 7-9 [2.2]Paracyclophane (1 eq.) is dissolved in dichloromethane (c=0.1 mol.L-1), stirred and cooled at 0° in an salt-ice bath. The acid chloride (2.1 eq.) and aluminum chloride (1.75 eq.) are suspended in dichloromethane (c=1 mol.L-1), cooled at 0°C and added quickly to the [2.2]paracyclophane solution under rapid stirring. Reaction mixture is maintained at 0°C for 15 min, pored onto ice and vigorously stirred until the organic layer becomes colorless. Diethyl ether is added until the organic layer becomes less dense than water. The organic layer is separated, washed twice with a saturated NaHCO 3 aqueous solution and finally with a a saturated NaCl aqueous solution. The organic layer is dried on MgSO 4 and the solvents are removed under reduced pressure. The crude product is purified by column chromatography on SiO 2. Elution petroleum ether/dichloromethane 3:2 v/v to remove the unreacted
New dyes based on BODIPY and tetrazine fluorophores connected through a phenyl spacer have been synthesized and their absorption, emission and electrochemical properties characterized. BODIPY can be reversibly oxidized into a stable cation radical whereas tetrazine can be reduced to a stable anion radical. The electrochemical and absorption studies demonstrate that both fluorophores behave independently. The bichromophoric compounds show an expected
A new series of distyryl-BODIPY has been rationally designed and synthesised from a novel fluorinated platform, 8-pentafluorophenylBODIPY, which has enhanced reactivity in the presence of both electron rich, and for the first time, electron deficient aldehydes. The pentafluorobenzene leads to larger red shifts of absorption and emission compared to previously reported analogues. The reactivity and spectroscopic results have been rationalised with quantum mechanics calculation. The fluorescence sensitivity of one derivative to acidity is also presented.
Original new fluorescent and electroactive compounds have been prepared, which feature two different fluorescent groups linked through an oxygen atom spacer. We describe here the synthesis, photophysical and electrochemical properties and their interplay, and our theoretical calculations. These molecules are composed of two fluorophores, an electron‐rich triphenylamine unit and an electron‐poor tetrazine unit. Although the bichromophores are not fluorescent in the neutral state due to a photoinduced electron transfer from the triphenylamine unit to the tetrazine unit, one can restore the fluorescence by oxydation of the triphenylamine moiety. Thus, a redox‐fluorescent switch has been realized.
The synthesis, photophysical and electrochemical properties as well as theoretical calculation studies of a newly designed triphenylamine derivative are described. This original compound displays one neutral form, three oxidized forms, and two protonated forms with distinct photophysical characteristics. The interplay of the emission with the protonation or the redox state (electrofluorochromism) has been explored and an on-off-on-off fluorescence switching was observed in the case of oxidation and an on-on-off fluorescence switching in the case of protonation.
A new boron dipyrromethene-ferrocene (BODIPY-Fc) conjugate with pentafluorophenyl as the meso substituent and two Fc termini was synthesized and its spectroscopic and electrochemical features were analysed. An intramolecular charge transfer from the donor Fc to the acceptor BODIPY has been predicted by theory and confirmed experimentally, leading to efficient fluorescence quenching when the dyad is in the neutral state. Fluorescence can be triggered by oxidizing both ferrocenyl units either chemically or electrochemically. Eventually, a fully reversible fluorescence switch is evidenced by coupling TIRF microscopy with electrolysis in an electrochemical cell.
We report here the design of two sets of multifluorophoric silica nanoparticles, observing unprecedented efficiencies in the energy-transfer processes among the doping dyes. These nanomaterials show a very high overall sensitization, allowing under a single wavelength excitation to obtain many different colors (one per nanoparticle) in emission with negligible crosstalk. Moreover, each particle can present very large and tunable pseudo-Stokes shifts (up to 435 nm), a very high brightness even exciting the bluest donor, and a negligible residual emission intensity from all donor dyes. All these features, combined with colloidal stability and synthetic method reliability, make these multicomponent nanoparticles very promising for multiplex analysis and for all the diagnostic techniques requiring high sensitivity associated with a large Stokes shift.
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