New Hindered BODIPY Derivatives: Solution and Amorphous State Fluorescence Properties

Abstract

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

Designing Dye–Nanochannel Antenna Hybrid Materials for Light Harvesting, Transport and Trapping

“…[40,109] Choosing the right chromophores which suit best for a specific application remains a large field to be explored. We mention as an example that the highly interesting class of Bodipy dyes [110] has been tested successfully for stopcock molecules, [40, 42, 80a] but not inserted into the channels, so far. Molecules that can enter the channels can also exit.…”

Synthesis and Characterization of Far‐Red/NIR‐Fluorescent BODIPY Dyes, Solid‐State Fluorescence, and Application as Fluorescent Tags Attached to Carbon Nano‐onions

“…Av ariety of different synthetic strategies to achieve solid-state fluorescence have been investigated. Leading examples include the introductiono fb ulky substituents, [14][15][16][17][18][19] dimerization, [20,21] and control over the BODIPY aggregation pattern by introducing trifluoromethyl substituents. [22] All of these approaches modify the BODIPY molecular structure to suppress p-p stacking of the BODIPY building blocks in the solid state.…”

Push–pull flexibly-bridged bis(haloBODIPYs): solvent and spacer switchable red emission

“…1), should avoid the non-radiative relaxation mechanism associated to the above-mentioned tolyl free motion. 17 Indeed, the mentioned ortho methylation places the meso-aryl groups of 5 (mesityl groups) in an almost orthogonal arrangement with respect to the corresponding indacene cores (PCM-B3LYP/6-31+g*; aryl-indacene dihedral angle ~89 o ).…”