0000000001305059
AUTHOR
Mathieu Berthelot
Synthesis and characterization of novel quinolyl porphyrins as receptors. Study of their association with halophenols and 4nitrophenol as a reference
International audience; In this work, new receptors built on the porphyrin scaffold were synthesized for halophenols recognition. A quinolyl group was introduced on the porphyrin's periphery as binding site, to form two series of molecules based on two distinct porphyrin frames and which were obtained in free base and zinc forms. The binding between these porphyrin based receptors and halophenols (2,3,4,6tetrachlorophenol, 2,4,6-trichlorophenol or 2,4,6-tribromophenol) was studied. As established by 1 H NMR spectroscopy, the binding constants are in the range of two-digit numbers, which value is correlated with the porphyrin structure (substitutive pattern, form of the free base or Zn II co…
Oxidative C-N fusion of pyridinyl-substituted porphyrins.
International audience; The mild (electro) chemical oxidation of pyridin-2-ylthio-meso substituted Ni(II) porphyrins affords C-N fused cationic and dicationic pyridinium-based derivatives. These porphyrins are fully characterized and the molecular structure of one of them was confirmed by X-ray crystallography. A mechanism for the intramolecular oxidative C-N coupling is proposed based on theoretical calculations and cyclic voltammetry analyses.
PI-Extension of porphyrins via intramolecular aromatic oxidative C-N coupling
Π-extension of porphyrins has been performed via intramolecular oxidative C-N coupling of peripheral pyridinyl fragment(s) with the porphyrin core. These fusion reactions lead to the formation of C-N bond(s) between the substituent(s) and the porphyrin. The precursors were functionnalized with 2-mercaptopyridine, 8-hydoxyquinoline and 2-picoline at their meso or β-pyrrolic positions via aromatic nucleophlic substitution, cross-coupling reaction or reaction of the macrocycle with organolithium reagents. Voltametric analyses revealed some marked differences on the reactivity of the porphyrins depending on their substitution pattern and metalation (nickel(II) or zinc(II)). Chemical and electro…
Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation
Four free base aminoporphyrins were synthesized in two steps via regioselective anodic nucleophilic substitution with pyridine followed by ring opening of the electrogenerated pyridinium with piperidine. The X-ray crystallographic structure of the unstable 2-aminotetraphenylporphyrin was solved. Protonation of this latter compound leads to the stable diiminium porphyrin salt.
Near-infrared emissive bacteriochlorin-diketopyrrolopyrrole triads: Synthesis and photophysical properties
International audience; The synthesis of unprecedented energy transfer triads containing a near-infrared (NIR) emissive bacteriochlorin subunit and two diketopyrrolopyrrole (DPP) moieties linked to each other via ethynyl or zero-carbon spacers is presented. Their optical and fluorescence properties were determined in CHCl3 and toluene. These photophysical measurements highlight the ability of DPP scaffold to act as an effective energy donor, which once excited in the range 450-550 nm resulting nearly exclusively NIR emission of hydroporphyrin (ETE > 96%). Since DPP dyes are valuable structurally tunable fluorophores that may be used in the construction of high-performance multicomponent pho…
CCDC 1919134: Experimental Crystal Structure Determination
Related Article: Julie Echaubard, Asmae Bousfiha, Mathieu Berthelot, Julien Roger, Paul Fleurat-Lessard, Hélène Cattey, Sophie Fournier, Charles H. Devillers, Dominique Lucas|2020|Eur.J.Inorg.Chem.|2020|551 |doi:10.1002/ejic.201900849
CCDC 1919135: Experimental Crystal Structure Determination
Related Article: Julie Echaubard, Asmae Bousfiha, Mathieu Berthelot, Julien Roger, Paul Fleurat-Lessard, Hélène Cattey, Sophie Fournier, Charles H. Devillers, Dominique Lucas|2020|Eur.J.Inorg.Chem.|2020|551 |doi:10.1002/ejic.201900849
CCDC 1557313: Experimental Crystal Structure Determination
Related Article: Mathieu Berthelot, Guillaume Hoffmann, Asmae Bousfiha, Julie Echaubard, Julien Roger, Hélène Cattey, Anthony Romieu, Dominique Lucas, Paul Fleurat-Lessard, Charles H. Devillers|2018|Chem.Commun.|54|5414|doi:10.1039/C8CC01375F
CCDC 1952439: Experimental Crystal Structure Determination
Related Article: Asmae Bousfiha, Abdou K. D. Dimé, Amelle Mankou-Makaya, Julie Echaubard, Mathieu Berthelot, Hélène Cattey, Anthony Romieu, Julien Roger, Charles H. Devillers|2020|Chem.Commun.|56|884|doi:10.1039/C9CC07351E
CCDC 1557314: Experimental Crystal Structure Determination
Related Article: Mathieu Berthelot, Guillaume Hoffmann, Asmae Bousfiha, Julie Echaubard, Julien Roger, Hélène Cattey, Anthony Romieu, Dominique Lucas, Paul Fleurat-Lessard, Charles H. Devillers|2018|Chem.Commun.|54|5414|doi:10.1039/C8CC01375F
CCDC 1813003: Experimental Crystal Structure Determination
Related Article: Mathieu Berthelot, Guillaume Hoffmann, Asmae Bousfiha, Julie Echaubard, Julien Roger, Hélène Cattey, Anthony Romieu, Dominique Lucas, Paul Fleurat-Lessard, Charles H. Devillers|2018|Chem.Commun.|54|5414|doi:10.1039/C8CC01375F
CCDC 1952440: Experimental Crystal Structure Determination
Related Article: Asmae Bousfiha, Abdou K. D. Dimé, Amelle Mankou-Makaya, Julie Echaubard, Mathieu Berthelot, Hélène Cattey, Anthony Romieu, Julien Roger, Charles H. Devillers|2020|Chem.Commun.|56|884|doi:10.1039/C9CC07351E