Thomas Bura

Université Laval

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Raymond Ziessel

Newcastle University

Mario Leclerc

Université Laval

Gilles Ulrich

Institut de Chimie et Procédés pour l'Energie, l'Environnement et la Santé

Pascal Retailleau

Institut de Chimie des Substances Naturelles

Serge Beaupré

Université Laval

Nicolas Leclerc

Institut de Chimie et Procédés pour l'Energie, l'Environnement et la Santé

T. Heiser

Laboratoire des Sciences de l'Ingénieur, de l'Informatique et de l'Imagerie

P. Lévêque

Laboratoire des Sciences de l'Ingénieur, de l'Informatique et de l'Imagerie

Marc‐André Légaré

McGill University

Antonio Cravino

Institut des Sciences et Technologies Moléculaires d'Angers

Cooperative Institutions

Centre National de la Recherche Scientifique

Université de Strasbourg

Institut Européen de Chimie et Biologie

Institut de Chimie et Procédés pour l'Energie, l'Environnement et la Santé

Laboratoire de Chimie Organique

Laboratoire de Chimie Moléculaire

Institut de Chimie

Université Laval

Institut de Physique et Chimie des Matériaux de Strasbourg

Laboratoire des Sciences de l'Ingénieur, de l'Informatique et de l'Imagerie

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Panchromatic Fluorescent Materials

Synfacts (2010)

Raymond Ziessel Thomas Bura Pascal Retailleau

An iterative method for the synthesis of covalently linked dyes is described. These molecules behave as antennas, effectively collecting the excitations and transferring them to the tri- or dimethyl Bodipy moieties.

BODIPY

Panchromatic film

10.1055/s-0030-1258732

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Citations (3)

Direct (Hetero)arylation Polymerization: Trends and Perspectives

Journal of the American Chemical Society (2016)

Thomas Bura J. Terence Blaskovits Mario Leclerc

Conjugated polymers have attracted much attention in recent years, as they can combine the best features of metals or inorganic semiconducting materials (excellent electrical and optical properties) with those of synthetic polymers (mechanical flexibility, simple processing, and low-cost production), thereby creating altogether new scientific synergies and technological opportunities. In the search for more efficient synthetic methods for the preparation of conjugated polymers, this Perspective reports advances in the field of direct (hetero)arylation polymerization. This recently developed polymerization method encompasses the formation of carbon–carbon bonds between simple (hetero)arenes and (hetero)aryl halides, reducing both the number of synthetic steps and the production of organometallic byproducts. Along these lines, we describe the most general and adaptable reaction conditions for the preparation of high-molecular-weight, defect-free conjugated polymers. We also discuss the bottleneck presented by the utilization of certain brominated thiophene units and propose some potential solutions. It is, however, firmly believed that this polymerization method will become a versatile tool in the field of conjugated polymers by providing a desirable atom-economical alternative to standard cross-coupling polymerization reactions.

Atom economy

10.1021/jacs.6b06237

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Citations (236)

Artificial Light-Harvesting Arrays: Electronic Energy Migration and Trapping on a Sphere and between Spheres

Journal of the American Chemical Society (2011)

Julien Iehl Jean‐François Nierengarten Anthony Harriman Thomas Bura Raymond Ziessel

A sophisticated model of the natural light-harvesting antenna has been devised by decorating a C(60) hexa-adduct with ten yellow and two blue boron dipyrromethene (Bodipy) dyes in such a way that the dyes retain their individuality and assist solubility of the fullerene. Unusually, the fullerene core is a poor electron acceptor and does not enter into light-induced electron-transfer reactions with the appended dyes, but ineffective electronic energy transfer from the excited-state dye to the C(60) residue competes with fluorescence from the yellow dye. Intraparticle electronic energy transfer from yellow to blue dyes can be followed by steady-state and time-resolved fluorescence spectroscopy and by excitation spectra for isolated C(60) nanoparticles dissolved in dioxane at 293 K and at 77 K. The decorated particles can be loaded into polymer films by spin coating from solution. In the dried film, efficient energy transfer occurs such that photons absorbed by the yellow dye are emitted by the blue dye. Films can also be prepared to contain C(60) nanoparticles loaded with the yellow Bodipy dye but lacking the blue dye and, under these circumstances, electronic energy migration occurs between yellow dyes appended to the same nanoparticle and, at higher loading, to dye molecules on nearby particles. Doping these latter polymer films with the mixed-dye nanoparticle coalesces these multifarious processes in a single system. Thus, long-range energy migration occurs among yellow dyes attached to different particles before trapping at a blue dye. In this respect, the film resembles the natural photosynthetic light-harvesting complexes, albeit at much reduced efficacy. The decorated nanoparticles sensitize amorphous silicon photocells.

10.1021/ja206894z

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Citations (151)

CCDC 1507661: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Thomas Bura Serge Beaupré Marc‐André Légaré Jesse Quinn Étienne Rochette

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1mlv79

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Absorption Tuning of Monosubstituted Triazatruxenes for Bulk Heterojunction Solar Cells

Organic Letters (2011)

Thomas Bura Nicolas Leclerc Sadiara Fall P. Lévêque T. Heiser

A series of triazatruxene (TAT)-functionalized Bodipy dyes were prepared by a sequence of reactions involving either cross-coupling reactions promoted by Pd complexes or a Knoevenagel reaction leading to a vinyl linker. The new dyes show large absorption coefficients and fluorescence quantum yields as well as interesting electrochemical properties. The blue dyes of this series exhibit interesting photovoltaic effects (VOC = 0.83 V, JSC = 3.6 mA/cm2, efficiency 0.9%) in bulk heterojunction solar cells, due to the good hole mobility imported by the TAT entity.

Knoevenagel condensation

BODIPY

Linker

Quantum Efficiency

Coupling reaction

10.1021/ol202443g

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Citations (71)

Multi-donor molecular bulk heterojunction solar cells: improving conversion efficiency by synergistic dye combinations

Journal of Materials Chemistry (2009)

Théodulf Rousseau Antonio Cravino Thomas Bura Gilles Ulrich Raymond Ziessel

Molecular bulk heterojunction solar cells with a power conversion efficiency of 1.70% have been fabricated using as donor BODIPY dyes with complementary light-harvesting properties.

BODIPY

Hybrid solar cell

10.1039/b903189h

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Citations (138)

Colour Tuning in a Novel Metal-free Organic Sensitizer (Bodipy) for Dye-sensitized Solar Cells

Chemistry - A European Journal (2009)

Duraisamy Kumaresan Randolph P. Thummel Thomas Bura Gilles Ulrich Raymond Ziessel

BODIPY

Organic dye

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p-Carborane-Bridged Bipyridine Ligands for Energy Transfer between Two Iridium Centers

Inorganic Chemistry (2013)

Marı́a Teresa Indelli Thomas Bura Raymond Ziessel

Two iridium(III) complexes displaying for one a high HOMO-LUMO gap and for the other a weaker gap were linked in a controlled and logical manner to closo-p-carborane spacers. The bridging ligand is composed of 5-ethynyl-2,2'-bipyridine units, and the peripherical Ir-ligands are orthometalated 2',4'-difluoro-2-phenylpyridine (dfppy) (λ(abs) at 400 nm for the "Ir(dfppy)2(bpy')") for the energy donor fragment and dibenzo[a,c]phenazine (dbpz) (λ(abs) at 525 nm for "Ir(dbpz)2(bpy')") for the energy acceptor fragment.Redox, spectroscopic, and photophysical properties for models and the donor-carborane-acceptor complex were determined. Efficient energy transfer from the "Ir(dfppy)2(bpy')" moiety to the "Ir(dbpz)2(bpy')" fragment is occurring with a rate constant of 3.3 × 10(8) s(-1) despite weak electronic coupling through the inert p-carborane spacer. From flash photolysis experiments it is shown that, by excitation of the donor, a low lying triplet state localized on the acceptor bridging ligand side is formed which decays by conversion to the (3)MLCT of the acceptor fragment which phosphoresces at 644 nm.

Acceptor

Bipyridine

Bridging ligand

Carborane

Moiety

Flash photolysis

HOMO/LUMO

10.1021/ic302222q

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Citations (21)

Alkynyl-substituted dipyrromethene-boron hydrophilic fluorescent compounds

HAL (Le Centre pour la Communication Scientifique Directe) (2010)