Chromophores and Macrocycles

Leader: Olivier Siri


Our researches are focused on three main axes: (1) near-infrared chromophores, (2) molecular sensors and (3) surface coating and engineering.

1. Near-infrared (NIR) chromophores

The access to highly conjugated chromophores exhibiting optical properties in low energies spectral regions (near-infrared, 750-3000 nm) is at the core of our activities since 2013. This domain is highly important, notably in bio-imaging, since it includes the biological transparency windows, which are choice spectral ranges to provide the best penetration depths and contrasts. In the field of molecular electronics, NIR dyes furthermore enable the elaboration of flexible, transparent photo-detectors used for the optical processing or treatment of signals, or incorporated in revolutionary devices mimicking the human eye.

However, chromophores possessing electronic transitions located in the NIR remain scarce. Their preparation often imply multiple synthetic steps yielding unsaturated compounds that are tedious to incorporate in devices or biological media, mainly due to limited solubility. Thus, our team develop original NIR dyes using relatively simple strategies (e.g. coordination and macrocyclic chemistries).

Most notably, we are investigating the synthesis of emerging quinoidal compounds such as the azacalixphyrins (Angew. Chem. Int. Ed., 2013, DOI : 10.1002/anie.201301217) and the benzoquinone diimine ligands (Chem. Commun. 2014, DOI : 10.1039/C4CC07353C ; Coord. Chem. Rev. 2017, DOI : 10.1016/j.ccr.2017.06.015), which present unprecedented pi-electrons distribution that can be controlled to adjust their reactivity or tune their electronical/optical properties depending on the target application (e.g. bio-imaging: Chem. Commun., 2018, DOI : 10.1039/C8CC05851B).


Équipe Siri 6

2. Molecular sensors

We are currently developing neutral and charged molecular sensors for homogeneous (liquid/liquid) or heterogeneous (solid/gas) detection of analytes.

Various approaches are investigated:
i) Azacalixarenes :

The calixarene skeleton is a popular macrocyclic platform used for the conception of simple to sophisticated supramolecular receptors because of its high flexibility. In contrast, the azacalix[4]arenes, incorporating bridging nitrogen atoms, were rarely used as hosts, since only two examples of supramolecular host-guest complexes were reported in the literature when we started these investigations. Such cavitants adopt a stable 1,3-alternate conformation both in solution and at the solid state, contributing to anions complexation (Chem. Eur. J., 2016, DOI : 10.1002/chem.201505089).

Équipe Siri 1

ii) Diamino-benzoquinone diimines:

The interest for these derivatives is expanding since their remarkable fundamental properties allow to envisage multiple perspectives in emerging technological fields. Indeed, diamino-benzoquinone diimines possess a 12-pi electrons system which is better described as constituted of two 6-pi electrons subunits which are chemically connected (C-C single bonds) but electronically independent. This exceptional distribution has been beneficial to trigger intramolecular reactions depending on the molecule’s environment. We demonstrated a unprecedented rearrangement of the quinones toward zwitterionic species, accompanied by a marked color change in solution and at the solid state (Mater. Chem. Front., 2018, DOI : 10.1039/C8QM00171E).

Équipe Siri 2



Two-step access to bis- meso -perfluoroalkyl-corroles towards meso -perfluoroacyl-ABC-corroles

Paul-Gabriel Julliard, Simon Pascal, Olivier Siri, Michel Giorgi, Diego Cortés-Arriagada, Luis Sanhueza, Gabriel Canard

Organic & Biomolecular Chemistry (2024)10.1039/D4OB00191E


Electrical monitoring of organic crystal phase transition using MoS2 field effect transistor

Ilan Boulet, Simon Pascal, F. Bedu, Igor Ozerov, Alain Ranguis, Thomas Leoni, Conrad Becker, Laurence Masson, Aleksandar Matkovic, Christian Teichert, Olivier Siri, Claudio Attaccalite, Jean-Roch Huntzinger, Matthieu Paillet, Ahmed-Azmi Zahab, Romain Parret

Nanoscale Advances 5:1681-1690 (2023)10.1039/d2na00817c

Tris‐benzo[cd]indole Cyanine Enables the NIR‐photosensitized Radical and Thiol‐ene Polymerizations at 940 nm

Christine Elian, Benjamin Mourot, Camil Benbouziyane, Jean-Pierre Malval, Sonia Lajnef, Fabienne Peyrot, Florian Massuyeau, Olivier Siri, Denis Jacquemin, Simon Pascal, Davy-Louis Versace

Angewandte Chemie International Edition (2023)10.1002/anie.202305963

Enzyme-immobilized hierarchically porous covalent organic framework biocomposite for catalytic degradation of broad-range emerging pollutants in water

Nada Elmerhi, Khadega Al-Maqdi, Khawlah Athamneh, Abdul Khayum Mohammed, Tina Skorjanc, Felipe Gándara, Jesus Raya, Simon Pascal, Olivier Siri, Ali Trabolsi, Iltaf Shah, Dinesh Shetty, Syed Salman Ashraf

Journal of Hazardous Materials 459:132261 (2023)10.1016/j.jhazmat.2023.132261

Azacalixphyrin nanostructures

Daniel Ferry, Sabrina Pricl, Domenico Marson, Zhongrui Chen, Gabriel Canard, Simon Pascal, Aura Tintaru, Olivier Siri

Journal of Porphyrins and Phthalocyanines (2023)10.1142/S1088424623500785

Core–Shell Multiwalled Carbon Nanotube/Cobalt Corrole Hybrids for the Oxygen Reduction Reaction

Paul-Gabriel Julliard, Manel Hanana, Laurent Alvarez, Renaud Cornut, Bruno Jousselme, Gabriel Canard, Stéphane Campidelli

Energy & Fuels 37:684-692 (2023)10.1021/acs.energyfuels.2c03434

The Diversity of Cucurbituril Molecular Switches and Shuttles

Anthony Kermagoret, David Bardelang

Chemistry - A European Journal 29 (2023)10.1002/chem.202302114

A pH-and Metal-Actuated Molecular Shuttle in Water

Amine Kriat, Simon Pascal, Brice Kauffmann, Yann Ferrand, David Bergé-Lefranc, Didier Gigmes, Olivier Siri, Anthony Kermagoret, David Bardelang

Chemistry - A European Journal e202300633 (2023)10.1002/chem.202300633

Controlled oligomeric guest stacking by cucurbiturils in water

Fengbo Liu, Amine Kriat, Roselyne Rosas, David Berge-Lefranc, Didier Gigmes, Simon Pascal, Olivier Siri, Simin Liu, Anthony Kermagoret, David Bardelang

Organic & Biomolecular Chemistry (2023)10.1039/D3OB01723K

Proton-coupled electron transfer in a pivaloyl-substituted dihydro-tetraazapentacene

Jean-François Longevial, Iryna Knysh, Shaymaa Al Shehimy, Lhoussain Khrouz, Arumugam Pandurangan, Simon Pascal, Gabriel Canard, Christophe Bucher, Denis Jacquemin, Olivier Siri

Electrochimica Acta 449:142224 (2023)10.1016/j.electacta.2023.142224

Insights into Extended Coupled Polymethines through the Investigation of Dual UV-to-NIR Acidochromic Switches Based on Heptamethine-Oxonol Dyes

Benjamin Mourot, Valérie Mazan, Mourad Elhabiri, Rudraditya Sarkar, Denis Jacquemin, Olivier Siri, Simon Pascal

Chemical Science (2023)10.1039/D3SC06126D

A Strategy to Design Substituted Tetraamino-Phenazine Dyes and Access to an NIR-Absorbing Benzoquinonediimine-Fused Quinoxaline

Tatiana Munteanu, Valérie Mazan, Mourad Elhabiri, Camil Benbouziyane, Gabriel Canard, Denis Jacquemin, Olivier Siri, Simon Pascal

Organic Letters (2023)10.1021/acs.orglett.3c01251

Deciphering electronic and structural effects in Copper Corrole/Graphene Hybrids

Kerry Wrighton-Araneda, Diego Cortés-Arriagada, Paulina Dreyse, Simon Pascal, Gabriel Canard, Luis Sanhueza

Chemistry - A European Journal (2023)10.1002/chem.202203175

Internal Dynamics and Modular Peripheral Binding in Stimuli‐Responsive 3 : 2 Host:Guest Complexes

Hang Yin, Roselyne Rosas, Stéphane Viel, Michel Giorgi, Valerie Monnier, Laurence Charles, Didier Siri, Didier Gigmes, Youssef Nassar, Floris Chevallier, Christophe Bucher, Ruibing Wang, Anthony Kermagoret, David Bardelang

Angewandte Chemie International Edition (2023)10.1002/anie.202315985

Breaking Azacalix[4]arenes into Induline Derivatives

Chen Zhongrui, Gabriel Canard, Grauby Olivier, Benjamin Mourot, Olivier Siri

Molecules 28 (2023)10.3390/molecules28248113


Circularly polarized luminescence of encaged Eu(iii) and Tb(iii) complexes controlled by an inherently chiral remote unit

Estelle Godart, Oriane Della-Negra, Augustin Long, Alberto Insuasty, Lorenzo Arrico, Costanza Benetti, Elise Antonetti, Paola Nava, Yoann Cotelle, Nicolas Vanthuyne, Marion Jean, Simon Pascal, Jean-Pierre Dutasta, Lorenzo Di Bari, Alexandre Martinez

New Journal of Chemistry 46:20154-20159 (2022)10.1039/d2nj02360a

Fully Zwitterionic Diaminobenzoquinonediimines Promoted by Cyanoaromatic N-substituents

Tereza Horáčková, Manon H.E. Bousquet, Adrien Morice, Ugo Triballier, Gabriel Canard, Pavel Lhoták, Denis Jacquemin, Simon Pascal, Olivier Siri

Dyes and Pigments (2022)10.1016/j.dyepig.2022.110681

NIR-to-NIR two-photon bio-imaging using very bright tailored amino-heptamethines dyes

Simon Pascal, San-Hui Chi, Alexei Grichine, Veronique Martel-Frachet, Joseph Perry, Olivier Maury, Chantal Andraud

Dyes and Pigments 203:110369 (2022)10.1016/j.dyepig.2022.110369

Synthesis and Electron Accepting Properties of Two Di(benz[f]indenone)-Fused Tetraazaanthracene Isomers

Bruno Salgues, Rudraditya Sarkar, Muhammad Fajri, Yatzil Avalos-Quiroz, Anne-Doriane Manick, Michel Giorgi, Nicolas Vanthuyne, Yannick Carissan, Christine Videlot-Ackermann, Jörg Ackermann, Gabriel Canard, Jean-Luc Parrain, Boris Le Guennic, Denis Jacquemin, Muriel Amatore, Laurent Commeiras, Elena Zaborova, Fréderic Fagès

Journal of Organic Chemistry 87:3276-3285 (2022)10.1021/acs.joc.1c02942

Covalent organic framework based on azacalix[4]arene for the efficient capture of dialysis waste products

Tina Skorjanc, Dinesh Shetty, Felipe Gándara, Simon Pascal, Nawavi Naleem, Salma Abubakar, Liaqat Ali, Abdul Khayum Mohammed, Jesus Raya, Serdal Kirmizialtin, Olivier Siri, Ali Trabolsi

ACS Applied Materials & Interfaces (2022)10.1021/acsami.2c06841

A one-dimensional high-order commensurate phase of tilted molecules

Anthony Thomas, Thomas Leoni, Olivier Siri, Conrad Becker, Martin Unzog, Christian Kern, Peter Puschnig, Peter Zeppenfeld

Physical Chemistry Chemical Physics 24:9118-9122 (2022)10.1039/d2cp00437b

Optoelectronic properties of a self-assembling rigidly-linked BF2-curcuminoid bichromophore

Claire Tonnelé, Manon Catherin, Michel Giorgi, Gabriel Canard, David Casanova, Frédéric Castet, Elena Zaborova, Frédéric Fages

Dyes and Pigments 207:110677 (2022)10.1016/j.dyepig.2022.110677

Energy‐Efficient Iodine Uptake by a Molecular Host⋅Guest Crystal

Xue Yang, Chunyang Li, Michel Giorgi, Didier Siri, Xavier Bugaut, Bastien Chatelet, Didier Gigmes, Mehdi Yemloul, Virginie Hornebecq, Anthony Kermagoret, Sophie Brasselet, Alexandre Martinez, David Bardelang

Angewandte Chemie International Edition 61:e202214039 (2022)10.1002/anie.202214039


Significance Of Nuclear Quantum Effects In Hydrogen Bonded Molecular Chains

Aleš Cahlík, Jack Hellerstedt, Jesús I Mendieta-Moreno, Martin Švec, Vijai M Santhini, Simon Pascal, Diego Soler-Polo, Sigurdur Erlingsson, Karel Výborný, Pingo Mutombo, Ondrej Marsalek, Olivier Siri, Pavel Jelínek

ACS Nano (2021)10.1021/acsnano.1c02572

Effect of the electron donating group on the excited-state electronic nature and epsilon-near-zero properties of curcuminoid-borondifluoride dyes

Kyu-Ri Choi, Dae Hyeon Kim, Yeon Ui Lee, Virginie Placide, Steven Huynh, Dandan Yao, Gabriel Canard, Elena Zaborova, Fabrice Mathevet, Loïc Mager, Benoît Heinrich, Jean-Charles Ribierre, Weon Jeong, Frédéric Fages, Anthony d'Aléo

RSC Advances 11:38247-38257 (2021)10.1039/d1ra08025c

Electronic and magnetic properties of metal–organic polymers with 4d and 5d-transition metal ions

Hassan Denawi, Mathieu Abel, Olivier Siri, Roland Hayn

Journal of Magnetism and Magnetic Materials 537:168183 (2021)10.1016/j.jmmm.2021.168183

Functionalized porphyrins from meso-poly-halogeno-alkyl-dipyrromethanes: synthesis and characterization

Paul-Gabriel Julliard, Simon Pascal, Olivier Siri, Diego Cortés-Arriagada, Luis Sanhueza, G. Canard

Comptes Rendus. Chimie 24:1-19 (2021)10.5802/crchim.97

On-surface chemistry using local high electric fields

Thomas Leoni, Tony Lelaidier, Anthony Thomas, Alain Ranguis, Olivier Siri, Claudio Attaccalite, Conrad Becker

Nanoscale Advances 3:5565-5569 (2021)10.1039/d1na00383f

Synthesis and biological evaluation of novel tetranuclear cyclopalladated complex bearing thiosemicarbazone scaffold ligand: Interactions with double-strand DNA, coronavirus, and molecular modeling studies

Zohreh Mehri Lighvan, Hossein Ali Khonakdar, Ali Akbari, Maryam Dehdashti Jahromi, Azar Ramezanpour, Anthony Kermagoret, Abolfazl Heydari, Esmaiel Jabbari

Applied Organometallic Chemistry 36 (2021)10.1002/aoc.6502

Near-infrared dyes for two-photon absorption in the short-wavelength infrared: strategies towards optical power limiting

Simon Pascal, Sylvain David, Chantal Andraud, Olivier Maury

Chemical Society Reviews (2021)10.1039/D0CS01221A


ChroMa group meetings - Every Wednesday at 13:00 - Room G2.14 (TPR1)

- 08/02/23 : Tatiana
- 15/02/23: Valentin
- 22/02/23: Benjamin
- 01/03/23: Axel
- 08/03/23: Vlad
- 15/03/23: Paul-Gabriel
- 22/03/23: Gaëlle
- 30/03/23: No group meeting
- 05/04/23: Tatiana
- 12/04/23: Valentin
- 19/04/23: No group meeting (HDR Anthony)
- 26/04/23: Benjamin
- 03/05/23: Axel
- 10/05/23: Vlad
- 17/05/23: Paul-Gabriel
- 24/05/23: Gaëlle
- 31/05/23: Quentin


  • ANR CONDOR (Olivier SIRI)


  • ECOS SUD (Gabriel CANARD)



  • Dr. Mourad Elhabiri, CBM, Université de Strasbourg
  • Prof. Denis Jacquemin, CEISAM, Université de Nantes
  • Dr. Anabella Da Silva, Institut Fresnel, Marseille
  • Pr. Marc Sallé & Dr. Sébastien Goeb, MOLTECH-Anjou, Angers
  • Dr. Anthony Kermagoret & Dr. David Bardelang, ICR, Marseille
  • Dr. Davy-Louis Versace, Institut de Chimie et des Matériaux Paris-Est


  • Pr. Teichert, Loeben (Autriche)
  • Pr. Jacek Ulański & Pr. Beata Łuszczyńska, Łódź (Pologne)
  • Pr. Pavel Jelinek, Prague (République Tchèque)
  • Pr. Ali Trabolsi, NYU Abu Dhabi (UAE)

Useful links