H. Li, J. Daniel, J.-B. Verlhac, M. Blanchard-Desce, N. Sojic

Chem. Eur. J., 201622, 12702-12714

A series of symmetric fluorescent dyes built from a spirofluorene core, bearing electroactive end-groups and having different conjugated linkers were prepared in view of their use as building blocks for the preparation of electrochemiluminescent (ECL) dyes and nanoparticles. Their electrochemical, spectroelectrochemical and ECL properties were first investigated in solution and structure/activity relationships were derived. The electrochemical and ECL properties show drastic variation that could be tuned contingent on the nature of the π-conjugated system, end-groups and of the core. Among the series, the highly fluorescent dye based on a spirofluorene core and triphenylamine end-groups connected via thiophene moieties (1) shows the most promising and intriguing properties. 1 is reversibly oxidized in three well-separated steps and a very intense and large ECL signal is generated. Its ECL efficiency is 4.5-time greater than that of the reference compound, Ru(bpy)32+.This remarkably high efficiency is due to the very good stability of the higher oxidized states and it makes 1 a very bright organic ECL luminophore. In addition, thanks to its molecular structure, this dye retains fluorescence when nano-precipitated in water, leading to Fluorescent Organic Nanoparticles (FONs). Redox behaviour of these FONs shows oxidation waves consistent with the initial molecular species. Finally, ECL from FONs made of 1 was recorded in water and strong ECL nano-emitters are thus obtained.

2016-09

La Chimie au Service d’une Délivrance de l’Insuline en Boucle Fermée
Wednesday, 19 December 2012
Messager L., Ancla C., Lapeyre V., Ravaine V., Catargi B.Médecine Clinique Endocrinologie et Diabète 2012, 59, 38-45.  
Indirect Bipolar Electrodeposition
Tuesday, 27 November 2012
Loget G., Roche J., Gianessi E., Bouffier L., Kuhn A.,J. Am. Chem.Soc. 2012, 134, 20033-20036. Based on the principles of bipolar electrochemistry, localized pH gradients are generated at the surface...
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Light-Emitting Electrochemical Swimmers
Monday, 08 October 2012
Sentic M., Loget G., Manojlovic D., Kuhn A., Sojic N.,Angew. Chem. Int. Ed. 2012, 51, 11284–11288. Swimmer in the dark: Propulsion of a conducting object is intrinsically coupled with light...
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Controlled Orientation of Asymmetric Copper Deposits on Carbon Microobjects by Bipolar Electrochemistry
Wednesday, 19 September 2012
Fattah Z., Garrigue P., Lapeyre V., Kuhn A., Bouffier L.,J. Phys. Chem. C 2012, 116, 22021-22027. Asymmetric particles of various chemical compositions have attracted great attention because of their...
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Quantification of Photoelectrogenerated Hydroxyl Radical on TiO2 by Surface Interrogation Scanning Electrochemical Microscopy
Tuesday, 07 August 2012
Zigah D., Rodriguez-Lopez P., Bard A. J.,Phys. Chem. Chem. Phys. 2012, 14, 12764-12772. Asymmetric particles of various chemical compositions have attracted great attention because of their...
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Development of Functionalized Cyclotriveratrylene Analogues: Introduction of Withdrawing and p-Conjugated Groups
Monday, 30 July 2012
Peyrard L., Dumartin M.-L., Chierici S., Pinet S., Jonusauskas G., Meyrand P., Gosse I.,J. Org. Chem. 2012, 77, 7023-7027. Cyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped...
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Electrochemistry and Bioactivity Relationship of 6-Substituted-4H-Pyrido[4,3,2-kl]acridin-4-one Antitumor Drug Candidates
Friday, 27 July 2012
Bouffier L., Gosse I., Demeunynck M., Mailley P.,Bioelectrochemistry 2012, 88, 103-109. We report here the electrochemical characterization of eight synthetic DNA intercalators based on the...
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True Bulk Synthesis of Janus Objects by Bipolar Electrochemistry
Monday, 16 July 2012
Loget G., Roche J., Kuhn A.,Adv. Mater. 2012, 24, 5111-5116. Cover article Janus particles have different features/chemistry on two opposite sides (see figure). So far, they have been obtained mainly...
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Direct Visualization of Symmetry Breaking during Janus Nanoparticle Formation
Tuesday, 03 July 2012
Loget G., Lee T.-C., Taylor R. W., Mahajan S., Nicoletti O., Jones S. T., Coulston R. J., Lapeyre V., Garrigue P., Midgley P. A., Scherman O. A., Baumberg J. J., Kuhn A.,Small 2012, 8, 2698-2703. The...
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Combined Macro/mesoporous Microelectrode Arrays (MEAs) for Low Noise Extracellular Recording of Neural Networks
Wednesday, 27 June 2012
Heim M., Rousseau L., Reculusa S., Urbanova V., Mazzocco C., Joucla S., Bouffier L., Vytras K., Bartlett P., Kuhn A., Yvert B.Journal of Neurophysiology 2012, 15, 1793-1803. Microelectrode arrays...
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Bulk Synthesis of Janus Objects and Asymmetric Patchy Particles
Thursday, 10 May 2012
Loget G., Kuhn A.,J. Mater. Chem. 2012, 22, 15457-15474. Feature article This review article highlights the most recent advances with respect to the preparation of Janus objects by bulk phase...
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Bipolar Electrochemistry for Cargo-lifting in Fluid Channels
Wednesday, 15 February 2012
Loget G., Kuhn A.,Lab on a Chip 2012, 12, 1967-1971. Hot Paper, Cover Article We report for the first time the vertical propulsion of conducting beads in liquid filled capillaries by bipolar...
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Origin and Control of Adhesion between Emulsion Drops Stabilised by Thermally-sensitive Soft Colloidal Particles
Friday, 20 January 2012
Destribats M., Lapeyre V., Sellier E., Leal Calderon F., Ravaine V., Schmitt V.,Langmuir 2012, 28, 3744-3755. We used soft microgels made of poly(N-isopropylacrylamide) (pNIPAM) of variable...
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Site Selective Generation of Sol-gel Deposits in Layered Bi-metallic Macroporous Electrode Architectures
Thursday, 19 January 2012
Lalo H., Bon Saint-Côme Y., Plano B., Etienne M., Walcarius E., Kuhn A.,Langmuir 2012, 28, 2323-2326. The elaboration of an original composite bimetallic macroporous electrode containing a...
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The Fraction of Alpha-linolenic Acid present in the sn-2 position of Structured Triacylglycerols decreases in Lymph Chylomicrons and Plasma Triacylglycerols during the Course of Lipid Absorption in Rats
Wednesday, 30 November 2011
Couedelo L., Vaysse C., Vaique E., Guy A., Gosse I., Durand T., Pinet S., Cansell M., Combe N.Journal of Nutrition 2012, 142, 70-75. Little is known about the ability of α-linolenic acid (Ln) to...
Engineering of Complex Macroporous Materials through Controlled Electrodeposition in Colloidal Superstructures
Tuesday, 29 November 2011
Heim M., Reculusa S., Ravaine S., Kuhn A.,Adv. Funct. Mater. 2012, 22, 538-545. Inside Cover Article Macroporous materials with a sophisticated architecture are obtained by electrochemical deposition...
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Electrochemical Investigations of Dissolved and Surface Immobilised 2-Amino-1,4-Naphthoquinones in Aqueous Solutions
Saturday, 29 October 2011
Bouffier L., Lister K. E., Higgins S. J., Nichols R. J., Doneux T.,J. Electroanal. Chem. 2012, 664, 80-87. The electrochemistry of proton coupled electron transfer phenomena is an important...
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Nanostructuration Strategies to Enhance Microelectrode Array (MEA) Performance for Neuronal Recording and Stimulation
Tuesday, 18 October 2011
Heim M., Yvert B., Kuhn A.,J. Physiology - Paris 2012, 106, 137-145. Microelectrode arrays (MEAs) are widely used tools for recording and stimulating extracellular neuronal activity. Major...
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