SMS

Smart Molecules and Surfaces

Leader: Jean-Manuel Raimundo

Introduction

The group is working on design, synthesis and characterization of photo- and electroactive organic compounds. The investigations involve:
Photochemistry

We study the relationship between the structure of organic compounds and their photochemical reactivity. A particular case is represented by design of photochromic molecules reversibly changing their color upon absorption of one or two photons. These molecules, especially those absorbing light in the visible range, are incorporated into solid matrices (sol-gel, polymers) and find several applications as solid-state filters, bioimaging and color photography.

 
 
Équipe Khodorkovsky

Electrochemistry

New strong organic electron donors and acceptors are characterized by their redox properties. Reversible redox systems exhibit electrochromic behavior and change their color depending on the applied potential. Such systems are important components of electroconductive materials and electrochromic displays.

Équipe Khodorkovsky 1

Quantum mechanical calculations

Quantum chemistry is an indispensable tool for predicting the properties of yet unknown organic molecules before attempting their synthesis.

Selected references

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.

Group leader

Researchers

University Lecturer

PhD Student

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

D/A cruciform bithiophene chromophores as potential molecular scaffolds for optoelectronic applications

Hecham Aboubakr, Chandrasekar Praveen, Volodymyr Malytskyi, Rene Sawadogo, Jean-Marc Sotiropoulos, Lénaïk Bélec, Hugues Brisset, Jean-Manuel Raimundo

Tetrahedron 72:1381-1386 (2016)10.1016/j.tet.2016.01.038

Chromenes involving a two-photon absorbing moiety: photochromism via intramolecular resonance energy transfer

Laura Bekere, Vladimir Lokshin, Mark Sigalov, Raz Gvishi, Peng Zhao, David J. Hagan, Eric W. van Stryland, Vladimir Khodorkovsky

New Journal of Chemistry 40:1143-1148 (2016)10.1039/c5nj02490k

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.

Facilities

  • JASCO UV-Vis spectrophotometer

  • Home-built system for advanced absorption and fluorescence measurements

  • Potentiostat

Patents

  • 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.