Alexis Quarré de Verneuil

Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation

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Errol Blart

Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation

Chantal Daniel

Institut de Chimie de Strasbourg

Léa Gimeno

Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation

Thierry Roisnel

Centre National de la Recherche Scientifique

Magali Allain

Institut des Sciences et Technologies Moléculaires d'Angers

Yann Pellegrin

Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation

Marina Coupeau

Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation

Jean‐Noël Rebilly

Centre National de la Recherche Scientifique

Christophe Gourlaouen

Centre National de la Recherche Scientifique

Bruno Linclau

University of Southampton

Cooperative Institutions

Centre National de la Recherche Scientifique

Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation

Nantes Université

Laboratoire de Synthèse Organique

Université Nantes Angers Le Mans

Université d'Angers

Institut de Chimie de Strasbourg

University of Southampton

Université de Rouen Normandie

Laboratoire de Mathématiques Jean Leray

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CCDC 1971784: Experimental Crystal Structure Determination

The Cambridge Structural Database (2021)

Léa Gimeno Errol Blart Jean‐Noël Rebilly Marina Coupeau Magali Allain

10.5517/ccdc.csd.cc245sy2

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Non‐Symmetrical Sterically Challenged Phenanthroline Ligands and Their Homoleptic Copper(I) Complexes with Improved Excited‐State Properties

Chemistry - A European Journal (2020)

Léa Gimeno Errol Blart Jean‐Noël Rebilly Marina Coupeau Magali Allain

A strategy is presented to improve the excited state reactivity of homoleptic copper-bis(diimine) complexes CuL2+ by increasing the steric bulk around CuI whereas preserving their stability. Substituting the phenanthroline at the 2-position by a phenyl group allows the implementation of stabilizing intramolecular π stacking within the copper complex, whereas tethering a branched alkyl chain at the 9-position provides enough steric bulk to rise the excited state energy E00 . Two novel complexes are studied and compared to symmetrical models. The impact of breaking the symmetry of phenanthroline ligands on the photophysical properties of the complexes is analyzed and rationalized thanks to a combined theoretical and experimental study. The importance of fine-tuning the steric bulk of the N-N chelate in order to stabilize the coordination sphere is demonstrated. Importantly, the excited state reactivity of the newly developed complexes is improved as demonstrated in the frame of a reductive quenching step, evidencing the relevance of our strategy.

Homoleptic

Reactivity

Phenanthroline

Diimine

10.1002/chem.202001209

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Citations (22)

CCDC 1972177: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Léa Gimeno Errol Blart Jean‐Noël Rebilly Marina Coupeau Magali Allain

10.5517/ccdc.csd.cc2466m6

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α‐Fluoro‐o‐cresols: The Key Role of Intramolecular Hydrogen Bonding in Conformational Preference and Hydrogen‐Bond Acidity

ChemPhysChem (2016)

Elena Bogdan Alexis Quarré de Verneuil François Besseau Guillaume Compain Bruno Linclau

The conformational preferences of o-cresols driven by fluorination were thoroughly investigated from a theoretical point of view with quantum-chemical methods, and the results were compared to those recently reported for benzyl alcohols. The key conformers of both families exhibit a six-membered intramolecular hydrogen-bond (IMHB) interaction. A significant enhancement in the strength of the IMHB is observed in α-fluoro-o-cresols, owing to a simultaneous increase in the hydrogen bond (HB) basicity of the aliphatic fluorine and the HB acidity of the aromatic hydroxyl relative to that observed for o-fluorobenzyl alcohols, which are characterized by aromatic fluorine atoms and aliphatic hydroxyl groups. In the cases of the di- and trifluorinated derivatives, the occurrence of a three-centered HB is emphasized, and its features are discussed. The impact of these structural predilections on the HB properties of o-cresol was characterized from the estimation of the HB acidity parameter, pKAHY , weighted according to their conformational populations. We found that α-fluorination led to a decrease in the HB acidity of the hydroxyl group (in contrast with the o-fluorination of benzyl alcohols), whereas α,α-difluorination resulted in no significant variation in pKAHY . Finally, an increase in the HB acidity was predicted upon methyl perfluorination, which was confirmed experimentally. Theoretical descriptors based on atoms in molecules, noncovalent interactions, and natural bond orbital analyses allowed rationalization of the predicted trends and revealed a relationship with the strength of the established OH⋅⋅⋅F IMHB.

Fluorine

Natural bond orbital

Atoms in molecules

Quantum Chemistry

Conformational isomerism

Non-covalent interactions

10.1002/cphc.201600453

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Citations (13)