NDLI: Bright Electrogenerated Chemiluminescence of a Bis-Donor Quadrupolar Spirofluorene Dye and Its Nanoparticles

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Li, Haidong Verlhac, Jean-baptiste Sojic, Neso Blanchard-desce, Mireille Daniel, Jonathan
Description	Author Affiliation: Li H ( Université Bordeaux, ISM, UMR 5255 CNRS, 33400, Talence, France.); Daniel J ( Université Bordeaux, ISM, UMR 5255 CNRS, 33400, Talence, France.); Verlhac JB ( Université Bordeaux, ISM, UMR 5255 CNRS, 33400, Talence, France.); Blanchard-Desce M ( Université Bordeaux, ISM, UMR 5255 CNRS, 33400, Talence, France. mireille.blanchard-desce@u-bordeaux.fr.); Sojic N ( Université Bordeaux, ISM, UMR 5255 CNRS, 33400, Talence, France. neso.sojic@u-bordeaux.fr.)
Abstract	A series of symmetric fluorescent dyes built from a spirofluorene core bearing electroactive end groups and having different conjugated linkers were prepared with a view to 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 by means of the nature of the π-conjugated system, the end groups, and the core. In this series, highly fluorescent dye 1 based on a spirofluorene core and triphenylamine end groups connected via thiophene moieties shows the most promising and intriguing properties. Dye 1 is reversibly oxidized in three well-separated steps and generates a very intense and large ECL signal. Its ECL efficiency is 4.5 times higher than that of the reference compound $[Ru(bpy)_{3}]^{2+}$ (bpy=2,2′-bipyridine). 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 after nanoprecipitation in water, which leads to fluorescent organic nanoparticles (FONs). The redox behavior 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 nanoemitters are thus obtained.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	36
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-08-26
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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