SMS

Smart Molecules and Surfaces

Responsable : Jean-Manuel Raimundo

Présentation

Le groupe travaille à la conception, la synthèse et la caractérisation de composés organiques photo- et électro-actifs.
Photochimie

Nous étudions les relations entre la structure de composés organiques et leur réactivité photochimique. Un exemple de choix est celui des molécules photochromes qui changent de couleur de manière réversible suite à l’absorption d’un ou deux photons. Ces dérivés, et plus particulièrement ceux absorbant dans le domaine du visible, sont incorporés dans des matrices solides (sol-gel, polymères) et trouvent de nombreuses applications en tant que filtres solides, ou dans les domaines de la bio-imagerie et la photographie couleur.

 
 
Équipe Khodorkovsky

Electrochimie

De nouveaux donneurs et accepteurs d’électrons forts sont caractérisés en terme de propriétés redox. Les systèmes redox réversibles présentent des propriétés électrochromiques et changent de couleur selon le potentiel appliqué. De tels systèmes sont des composants incontournables des matériaux électroconducteurs d’affichages électrochromes.

Équipe Khodorkovsky 1

Calculs de mécanique quantique

La chimie quantique est un outil indispensable pour prédire les propriétés de composés jusqu’alors inconnus avant même de développer leur synthèse.

Quelques  références

Lokshin, V., Khodorkovsky, V. (2018). Stereochemistry in control of photochemical reactivity: 2,6-Diaryl-4 H -spiro[cyclohexane-1,2′-indene]-1′,3′,4-triones. Tetrahedron, 74(3), 418-424.

Bekere, L., Lokshin, V., Sigalov, M., Gvishi, R., Zhao, P., Hagan, D. J., Khodorkovsky, V. (2016). Chromenes involving a two-photon absorbing moiety: photochromism via intramolecular resonance energy transfer. New J. Chem., 40 (2), 1143-1148.

Lokshin, V., Bekere, L., Khodorkovsky, V. (2017). Visual light photoswitches derived from bindone: Toward stabilization of colored photo-isomers. Dyes and Pigments, 145, 570-575.

Niebel, C., Lokshin, V., & Khodorkovsky, V. (2010). Octacyanotetramethylene-substituted dicyclopentanaphthalene: a new anionic electron acceptor with multi-stage reversible redox behavior. Tetrahedron Letters, 51(6), 949-951.

Bar, G., Larina, N., Grinis, L., Lokshin, V., Gvishi, R., Kiryuschev, I., Khodorkovsky, V. (2012). RGB organic electrochromic cells. Solar Energy Materials and Solar Cells, 99, 123-128.

Responsable

Chercheurs

Enseignants-chercheurs

Doctorants

Publications

2022

Affinity driven ion exchange EG-OFET sensor for high selectivity and low limit of detection of Cesium in seawater

Tin Phan Nguy, Volkan Kilinc, Ryoma Hayakawa, Catherine Henry-De-Villeneuve, Jean-Manuel Raimundo, Yutaka Wakayama, Anne Charrier

Sensors and Actuators B: Chemical 351:130956 (2022)10.1016/j.snb.2021.130956

Affinity driven ion exchange EG-OFET sensor for high selectivity and low limit of detection of cesium in seawater

Tin Phan Nguy, Volkan Kilinc, Ryoma Hayakawa, Catherine Henry-De-Villeneuve, Jean-Manuel Raimundo, Yutaka Wakayama, Anne Charrier

Sensors and Actuators B: Chemical 351:130956 (2022)10.1016/j.snb.2021.130956

Conjugated donor–acceptor substituted systems involving the 1,3-indandione-derived electron accepting moieties

Mark Sigalov, Royi Mazor, Arkady Ellern, Nina Larina, Vladimir Lokshin, Vladimir Khodorkovsky

RSC Advances 12:27766-27774 (2022)10.1039/d2ra05335g

2021

Dipole moments of conjugated donor–acceptor substituted systems: calculations vs. experiments

Vladimir Lokshin, Mark Sigalov, Nina Larina, Vladimir Khodorkovsky

RSC Advances 11:934-945 (2021)10.1039/d0ra10182f

Light-Induced Reactions within Poly(4-vinyl pyridine)/Pyridine Gels: The 1,6-Polyazaacetylene Oligomers Formation

Evgenia Vaganova, Dror Eliaz, Ulyana Shimanovich, Gregory Leitus, Emad Aqad, Vladimir Lokshin, Vladimir Khodorkovsky

Molecules 26:6925 (2021)10.3390/molecules26226925

2020

Control of the optical properties upon a reversible [2+2] cycloaddition of 3-(4-N,N-dibutylamino)-styryl)-3’-(dicyanovinyl)-bithiophene

Hecham Aboubakr, Jean-Marc Sotiropoulos, Hugues Brisset, Jean-Manuel Raimundo

Tetrahedron 76:131384 (2020)10.1016/j.tet.2020.131384

Phosphonium-ammonium-based di-cationic ionic liquids as antibacterial over the ESKAPE group

Frédéric Brunel, Christelle Lautard, Frédéric Garzino, Jean-Manuel Raimundo, Jean-Michel Bolla, Michel Camplo

Bioorganic and Medicinal Chemistry Letters 30:127389 (2020)10.1016/j.bmcl.2020.127389

Femtomolar detection of Cu2+ ions in solution using super-Nernstian FET-sensor with a lipid monolayer as top-gate dielectric

A. Kenaan, F. Brunel, J.-M. Raimundo, Anne Charrier

Sensors and Actuators B: Chemical 316:128147 (2020)10.1016/j.snb.2020.128147

Spiro 1,3-indandiones: intramolecular photochemical reactions of carbonyl groups with carbon-carbon double bonds

Vladimir Lokshin, Hervé Clavier, Vladimir Khodorkovsky

New Journal of Chemistry 44:14373-14378 (2020)10.1039/D0NJ02923H

Recent Electrochemical/Electrical Microfabricated Sensor Devices for Ionic and Polyionic Analytes

Pedro Martín Várguez, Frédéric Brunel, Jean-Manuel Raimundo

ACS Omega 5:4733-4742 (2020)10.1021/acsomega.9b04331

Electrolyte-gated-organic field effect transistors functionalized by lipid monolayers with tunable pH sensitivity for sensor applications

Tin Phan Nguy, Ryoma Hayakawa, Volkan Kilinc, Matthieu Petit, Yemineni S L V Narayana, Masayoshi Higuchi, Jean-Manuel Raimundo, Anne Charrier, Yutaka Wakayama

Applied Physics Express 13:011005 (2020)10.7567/1882-0786/ab5322

Hindered rotational barriers in conjugated donor–acceptor substituted systems: calculations vs. experiments

Mark Sigalov, Vladimir Lokshin, Nina Larina, Vladimir Khodorkovsky

Physical Chemistry Chemical Physics 22:1214-1221 (2020)10.1039/c9cp06234c

2019

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

Arnault Heynderickx, Sébastien Nénon, Olivier Siri, Vladimir Lokshin, Vladimir Khodorkovsky

Beilstein Journal of Organic Chemistry 15:2059-2068 (2019)10.3762/bjoc.15.203

Novel and Innovative Interface as Potential Active Layer in Chem-FET Sensor Devices for the Specific Sensing of Cs+

Volkan Kilinc, Catherine Henry-De-Villeneuve, Tin Phan Nguy, Yutaka Wakayama, Anne M Charrier, Jean-Manuel Raimundo

ACS Applied Materials & Interfaces 11:47635-47641 (2019)10.1021/acsami.9b18188

Novel and innovative interface as potential active layer in Chem-FET sensor devices for the specific sensing of Cs

Volkan Kilinc, Catherine Henry-De-Villeneuve, Tin Phan Nguy, Yutaka Wakayama, Anne Charrier, Jean-Manuel Raimundo

ACS Applied Materials & Interfaces 11:47635-47641 (2019)10.1021/acsami.9b18188

Bacterial anti-adhesion activity based on the electrochemical properties of polymethacrylates bearing ferrocenyl pendant groups

Ronald Nguema Edzang, The Hy Duong, Jean-François Briand, Marlene Lejars, Jean-Manuel Raimundo, Christine Bressy, Hugues Brisset

Biofouling 34:1055-1063 (2019)10.1080/08927014.2018.1539165

Stable operation of water-gated organic field-effect transistor depending on channel flatness, electrode metals and surface treatment

Tin Phan Nguy, Ryoma Hayakawa, Volkan Kilinc, Matthieu Petit, Jean-Manuel Raimundo, Anne Charrier, Yutaka Wakayama

Japanese Journal of Applied Physics 58:SDDH02 (2019)10.7567/1347-4065/ab09d2

What Can Be Learned from the Polymerization of a Pyridine‐Based Two‐Component System

Evgenia Vaganova, Faina Dubnikov, Ellina Kesselman, Vladimir Lokshin, Vladimir Khodorkovsky

Macromolecular Symposia 385:1800157 (2019)10.1002/masy.201800157

2018

A red to blue series of push-pull dyes for NiO based p-DSSCs.

Romain Brisse, Praveen Chandrasekar, Valentin Maffeis, Tiphaine Bourgeteau, Denis - Tondelier, Thomas Berthelot, Bernard Geffroy, Thomas Gustavsson, Jean-Manuel Raimundo, Bruno Jousselme

Sustainable Energy & Fuels 2:648-654 (2018)10.1039/C7SE00474E

Antibacterial activities of mono-, di- and tri-substituted triphenylamine-based phosphonium ionic liquids

Frédéric Brunel, Christelle Lautard, Carole Di Giorgio, Frédéric Garzino, Jean-Manuel Raimundo, Jean-Michel Bolla, Michel Camplo

Bioorganic and Medicinal Chemistry Letters 28:926-929 (2018)10.1016/j.bmcl.2018.01.057

Ultra-thin supported lipid monolayer with unprecedented mechanical and dielectric properties

Ahmad Kenaan, Racha El Zein, Volkan Kilinc, Sébastien Lamant, Jean-Manuel Raimundo, Anne Charrier

Advanced Functional Materials 1801024 (2018)10.1002/adfm.201801024

Thiol-functionalization of Mn5Ge3 thin films

Marta K Schütz, Matthieu Petit, Lisa Michez, Alain Ranguis, Guillaume Monier, Christine Robert-Goumet, Jean-Manuel Raimundo

Applied Surface Science 451:191-197 (2018)10.1016/j.apsusc.2018.04.231

2017

Visual light photoswitches derived from bindone: Toward stabilization of colored photo-isomers

Vladimir Lokshin, Laura Bekere, Vladimir Khodorkovsky

Dyes and Pigments 145:570-575 (2017)10.1016/j.dyepig.2017.06.052

2016

Subpicomolar Iron Sensing Platform Based on Functional Lipid Monolayer Microarrays

Ahmad Kenaan, Tuyen D. Nguyen, Herve Dallaporta, Jean-Manuel Raimundo, Anne M. Charrier

Analytical Chemistry 88:3804-3809 (2016)10.1021/acs.analchem.5b04834

An introduction to photocatalysis through methylene blue photodegradation

Matthieu Petit, Lisa Michez, Jean-Manuel Raimundo, Tuhiti Malinowski, Philippe Dumas

European Journal of Physics 37:065808 (2016)10.1088/0143-0807/37/6/065808

Financement

Ingénierie moléculaire et matériaux fonctionnelsSources et sondes ponctuelles 2

  • Nanohybrids for multiphoton excitation (NEM). ANR Blanc. ANR, 2009- 2011.

  • Color photo technology for electronic ID documents (COSEC-ID), (Euripides certified, Ministry of Industry) 2010 – 2014.

  • Preparation of one-photon absorbing photochromes. KILOLAMBDA TECHNOLOGIES, LTD, 2017.

Équipements

  • Spectrophotomètre UV-Vis JASCO

  • Système avancé de mesure d’absorption et de fluorescence

  • Potentiostat

Brevets

  • A mechanism and apparatus by which visual information and/or color images may be securely and inexpensively personalized onto physical media by selectively bleaching color components

J.-L. Lesur, J. Leibenguth, V. Khodorkovsky, N. Larina, V. Lokshin, M. Maciejczyk. Patent application. CNRS Ref. No 06214-01.