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
Latex nanoparticles functionalized with cyclam (1,4,8,11-tetraazacyclotetradecane), a copper chelator, have been doped with a fluorescent dye (BODIPY derivative: 4,4-difluoro-8-(2',4',6'-trimethyl)phenyl-2,6-diethyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene). The bulky, hydrophobic fluorophore dissolves within the nanoparticles' polymer core up to a concentration of about 88.4 micromol g(-1). At this concentration the fluorescence yield is about 0.80. Adding Cu2+ ions to the solution decreases the fluorescence because of the energy transfer between the dye and the violet copper cyclam complexes. The response is fast: 90% of the quenching occurs within 1 s. The Cu2+ detection threshold is of 1 nanomolar. No interferences were observed with zinc and nickel ions.
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