0000000000307295
AUTHOR
Marc Sallé
Tuning the electronic properties and the planarity degree in the π-extended TTF series: the prominent role of heteroatoms
The main asset of small molecules for application in organic electronics lies in the tunability of their electronic properties owing to the precise control of their molecular design. Semiconducting properties in organic compounds are for instance closely linked to the molecular planarity degree, including when considering various redox states. Among those species, the π-extended TTF (exTTF: 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene) presents fascinating redox and structural properties, which have been extensively studied in various fields of organic electronics. Here we show that S-exTTF, a sulfur enriched π-isoelectronic dithieno analogue of pristine exTTF, synthesized through…
π conjugation across the tetrathiafulvalene core: Synthesis of extended tetrathiafulvalene derivatives and theoretical analysis of their unusual electrochemical properties
A series of extended tetrathiafulvalene (TTF) derivatives bearing one or two 1,4-dithiafulven-6-yl substitutents has been prepared. The new compounds present remarkable electrochemical singularities compared with other TTF derivatives, which are strongly affected by the nature of the substitution on the lateral heterocycle(s). This unusual electrochemical behaviour follows a square-scheme sequence and is attributed to structural changes upon oxidation of the pi-donating molecules. Digital simulations of the electrochemical data have been used to reach the values of the kinetic and thermodynamic constants involved in the square scheme. Theoretical calculations establish an important contribu…
Controlling the Host-Guest Interaction Mode through a Redox Stimulus
International audience; A proof-of-concept related to the redox-control of the binding/releasing process in a host-guest system is achieved by designing a neutral and robust Pt-based redox-active metallacage involving two extended-tetrathiafulvalene (exTTF) ligands. When neutral, the cage is able to bind a planar polyaromatic guest (coronene). Remarkably, the chemical or electrochemical oxidation of the host-guest complex leads to the reversible expulsion of the guest outside the cavity, which is assigned to a drastic change of the host-guest interaction mode, illustrating the key role of counteranions along the exchange process. The reversible process is supported by various experimental d…
First signals of electrochemically oxidized species of TTF and TMT-TTF : a study by in situ spectroelectrochemical FTIR and DFT calculations
A first study by in situ FTIR spectroelectrochemistry of TTF and TTM-TTF has been undertaken. The oxidation, in this case, is caused only by electrochemistry, which constitutes a clear advantage over chemical oxidation since no side products are present in the solution. In this context, we obtained the signals of neutral, radical cation, and dication species of TTF and TTM-TTF. The experimental conditions were chosen in order to avoid the possible formation of π-dimer species and to obtain a satisfactory signal-to-noise ratio. A weak signal was detected for TTF and a stronger one for TTM-TTF. The changes induced by the oxidation process in the IR spectra of TTF and TTM-TTF have been analyze…
O-Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes
Herein we report an efficient synthesis to prepare O‐doped nanographenes, which derive from the longitudinally and latitudinally p‐extension of pyrene. The derivatives are highly fluorescent and feature low‐oxidation potentials. Exploiting electrooxidation, crystals of cationic mixed valence (MV) complexes were grown in which the organic salts organize into face‐to‐face p‐ p stacks, a favorable solid‐state arrangement for organic electronics. Variable‐temperature EPR measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar p‐stacking architectures. Electric measurements of single crystals of the MV salts exhibited a semiconduct…
CCDC 1557895: Experimental Crystal Structure Determination
Related Article: Luka Ðorđević, Cataldo Valentini, Nicola Demitri, Cécile Mézière, Magali Allain, Marc Sallé, Andrea Folli, Damien Murphy, Samuel Mañas-Valero, Eugenio Coronado, Davide Bonifazi|2020|Angew.Chem.,Int.Ed.|59|4106|doi:10.1002/anie.201914025
CCDC 1920493: Experimental Crystal Structure Determination
Related Article: Luka Ðorđević, Cataldo Valentini, Nicola Demitri, Cécile Mézière, Magali Allain, Marc Sallé, Andrea Folli, Damien Murphy, Samuel Mañas-Valero, Eugenio Coronado, Davide Bonifazi|2020|Angew.Chem.,Int.Ed.|59|4106|doi:10.1002/anie.201914025
CCDC 1834564: Experimental Crystal Structure Determination
Related Article: Serhii Krykun, Vincent Croué, Magali Allain, Zoia Voitenko, Juan Aragó, Enrique Ortí, Sébastien Goeb, Marc Sallé|2018|J.Mater.Chem.C|6|13190|doi:10.1039/C8TC04730H
CCDC 1557896: Experimental Crystal Structure Determination
Related Article: Luka Ðorđević, Cataldo Valentini, Nicola Demitri, Cécile Mézière, Magali Allain, Marc Sallé, Andrea Folli, Damien Murphy, Samuel Mañas-Valero, Eugenio Coronado, Davide Bonifazi|2020|Angew.Chem.,Int.Ed.|59|4106|doi:10.1002/anie.201914025
CCDC 1562676: Experimental Crystal Structure Determination
Related Article: György Szalóki, Vincent Croué, Vincent Carré, Frédéric Aubriet, Olivier Alévêque, Eric Levillain, Magali Allain, Juan Aragó, Enrique Ortí, Sébastien Goeb, Marc Sallé|2017|Angew.Chem.,Int.Ed.|56|16272|doi:10.1002/anie.201709483
CCDC 1834563: Experimental Crystal Structure Determination
Related Article: Serhii Krykun, Vincent Croué, Magali Allain, Zoia Voitenko, Juan Aragó, Enrique Ortí, Sébastien Goeb, Marc Sallé|2018|J.Mater.Chem.C|6|13190|doi:10.1039/C8TC04730H
CCDC 1912053: Experimental Crystal Structure Determination
Related Article: Luka Ðorđević, Cataldo Valentini, Nicola Demitri, Cécile Mézière, Magali Allain, Marc Sallé, Andrea Folli, Damien Murphy, Samuel Mañas-Valero, Eugenio Coronado, Davide Bonifazi|2020|Angew.Chem.,Int.Ed.|59|4106|doi:10.1002/anie.201914025
CCDC 1936956: Experimental Crystal Structure Determination
Related Article: Luka Ðorđević, Cataldo Valentini, Nicola Demitri, Cécile Mézière, Magali Allain, Marc Sallé, Andrea Folli, Damien Murphy, Samuel Mañas-Valero, Eugenio Coronado, Davide Bonifazi|2020|Angew.Chem.,Int.Ed.|59|4106|doi:10.1002/anie.201914025
CCDC 1557894: Experimental Crystal Structure Determination
Related Article: Luka Ðorđević, Cataldo Valentini, Nicola Demitri, Cécile Mézière, Magali Allain, Marc Sallé, Andrea Folli, Damien Murphy, Samuel Mañas-Valero, Eugenio Coronado, Davide Bonifazi|2020|Angew.Chem.,Int.Ed.|59|4106|doi:10.1002/anie.201914025
CCDC 1562675: Experimental Crystal Structure Determination
Related Article: György Szalóki, Vincent Croué, Vincent Carré, Frédéric Aubriet, Olivier Alévêque, Eric Levillain, Magali Allain, Juan Aragó, Enrique Ortí, Sébastien Goeb, Marc Sallé|2017|Angew.Chem.,Int.Ed.|56|16272|doi:10.1002/anie.201709483
CCDC 1834566: Experimental Crystal Structure Determination
Related Article: Serhii Krykun, Vincent Croué, Magali Allain, Zoia Voitenko, Juan Aragó, Enrique Ortí, Sébastien Goeb, Marc Sallé|2018|J.Mater.Chem.C|6|13190|doi:10.1039/C8TC04730H