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Massue J.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Frath D.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Retailleau P.,French National Center for Scientific Research | Ulrich G.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Ziessel R.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa
Chemistry - A European Journal | Year: 2013

A series of thirteen luminescent tetrahedral borate complexes based on the 2-(2′-hydroxyphenyl)benzoxazole (HBO) core is presented. Their synthesis includes the incorporation of an ethynyl fragment by Sonogashira cross-coupling reaction, with the goal of extending the conjugation and consequently redshifting their emission wavelength. Different regioisomers, substituted in the 3-, 4-, or 5-position of the phenolate side of the HBO core, were studied in order to compare their photophysical properties. The complexes were characterized by X-ray diffraction and NMR, UV/Vis, and emission spectroscopy in solution and in the solid state. In all cases, complexation to boron leads to a donor-acceptor character that impacts their photophysical properties. Complexes with a 3- or 5-substituted fragment display mild to pronounced internal charge transfer (ICT), a feature strengthened by the presence of p- dibutylaminophenylacetylene in the molecular structure, protonation of the nitrogen atom of which leads to a significant blueshift and an increase in quantum yield. On the contrary, when the ethynyl module is grafted on the 4-position, narrow, structured, symmetrical absorption/emission bands are observed. Moreover, the fact that protonation has little effect on the emission maximum wavelength reveals singlet excited-state decay. Solid-state emission properties reveal a redshift compared to solution, explained by tight packing of the π-conjugated systems and the high planarity of the dyes. Subsequent connection of these complexes to other photoactive subunits (BODIPY, Boranil) provides dyads in which efficient cascade energy transfer is observed. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Hablot D.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Sutter A.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Retailleau P.,French National Center for Scientific Research | Ziessel R.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa
Chemistry - A European Journal | Year: 2012

Fluorescent nanorods: Donor-acceptor dyads based on novel unsymmetrically disubstituted closo-1,12-dicarbadecaboranes have been prepared in a completely controlled manner by using a three-step procedure. Dyads with different donor-acceptor spacing were thereby obtained. Efficient energy transfer from the donor to the acceptor was determined in fluid solution at room temperature. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Source


Massif C.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Dautrey S.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Haefele A.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Ziessel R.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | And 6 more authors.
Organic and Biomolecular Chemistry | Year: 2012

New synthetic methodologies for the efficient chemical conversion of hydrophobic fluorescent dyes into bioconjugable and water-soluble derivatives are described. The combined use of an original sulfonated terminal alkyne and a metal-mediated reaction, namely the copper-catalysed Huisgen 1,3-dipolar cycloaddition ("click" reaction) or the Sonogashira cross-coupling, is the cornerstone of these novel post-synthetic sulfonation approaches. © 2012 The Royal Society of Chemistry. Source


Camerel F.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Donnio B.,CNRS Institute of Genetics and of Molecular and Cellular Biology | Ziessel R.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa
Soft Matter | Year: 2011

Two novel families of highly functionalized molecules consisting of a central carbazole or naphthalene core carrying actionable acid functions and linked to gallate platforms equipped with three long alkoxy chains have been rationally designed. The presence of amide tethers and chelating rigid fragments generate a new class of luminescent mesomorphic materials. Platforms bearing long paraffin chains (n = 12 and 16) self-organize into columnar liquid crystalline phases in which the columns are arranged according to a 2D oblique, rectangular or hexagonal lattice symmetry as deduced from powder XRD experiments. FT-IR studies confirm that the common driving force for aggregation and micro-segregation in the mesophase is due to the occurrence of a tight intermolecular H-bonded network. Spectroscopic measurements show that these platforms are luminescent in solution and in the solid state. Due to the synthetic availability of carbazole and naphthalene rigid cores and the simplicity by which these platforms can be graphed, this methodology represents a practical alternative to the production of fluorescent and mesomorphic materials. © 2011 The Royal Society of Chemistry. Source


Niu S.-L.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Massif C.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Ulrich G.,Laboratoire Of Chimie Moleculaire Et Spectroscopies Avancees Lcosa | Renard P.-Y.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | And 5 more authors.
Chemistry - A European Journal | Year: 2012

A series of water-soluble red-emitting distyryl-borondipyrromethene (BODIPY) dyes were designed and synthesized by using three complementary approaches aimed at introducing water-solubilizing groups on opposite faces of the fluorescent core to reduce or completely suppress self-aggregation. An additional carboxylic acid functional group was introduced at the pseudo-meso position of the BODIPY scaffold for conjugation to amine-containing biomolecules/biopolymers. The optical properties of these dyes were evaluated under simulated physiological conditions (i.e., phosphate-buffered saline (PBS), pH7.5) or in pure water. The emission wavelength (λ max) of these labels was found in the 640-660nm range with quantum yields from modest to unprecedentedly high values (4 to 38%). The bioconjugation of these distyryl-BODIPY dyes with bovine serum albumin (BSA) and the monoclonal antibody (mAb) 12A5 was successfully performed under mild aqueous conditions. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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