Yann Trolez

Associate professor

Yann Trolez

Email : yann [dot] trolez [at] ensc-rennes [dot] fr

Phone : +33 2 23 23 80 69

Office number : 110 (ENSCR)

News

Our latest article on TCBDs is out: https://pubs.rsc.org/en/content/articlelanding/2021/cp/d1cp03346h

We don't have any postdoc opportunity in the group at the moment.

Biography

Yann Trolez obtained his PhD degree from the University of Strasbourg in 2010. His thesis was supervised by Jean-Paul Collin and Jean-Pierre Sauvage. It dealt with the synthesis and study of cyclic and linear multi-rotaxanes. After a postdoctoral stay at ETH Zürich in the group of François Diederich working in the field of allenic and acetylenic chemistry, he was appointed assistant professor in 2011 at the Ecole Nationale Supérieure de Chimie de Rennes to work with Jean-Claude Guillemin. In 2015, he spent one year supported by the CNRS in the group of Philippe Gros working on the synthesis of iron(II) complexes for photovoltaics. In 2019, he passed his habilitation (HDR) to become associate professor. He co-authored 37 publications.

https://orcid.org/0000-0002-5421-9556

Twitter handle: @YTrolez

Research interests

The group is mainly interested in the synthesis and reactivity of acetylenic compounds. Two different fields are developed.

1) Synthesis and chemistry of conjugated diynes and triynes

We are interested in cyanopolyynes (H-(C≡C)n-CN), which were detected in the interstellar medium for n = 1 to 4, and derivatives. We published new syntheses of cyanobutadiyne (Angew. Chem. Int. Ed. 2005) and methylcyanobutadiyne (Chem. Eur. J. 2013, J. Org. Chem. 2016). We also perform photolyses experiments in the gas phase in order to understand how these molecules could be formed in the interstellar medium, and experiments in the condensed phase to examine their reactivity. Synthetic methodology is thus a key aspect of our research to access the target compounds. Unprecedented reactivity is also investigated (Chem. Eur. J. 2015). Recently, we have been able to synthesize conjugated triynes by alkyne metathesis (Chem. Sci. 2020, Organometallics 2021).

2) Synthesis and study of new 1,1,4,4-tetracyanobutadienes

We recently showed that a certain number of ynamides reacted very well with tetracyanoethylene to give 1,1,4,4-tetracyanobutadienes (TCBDs) in high yields, following a sequence of [2+2]cycloaddition-[2+2]retroelectrocyclization (Chem. Eur. J. 2014; Chem. Asian J. 2017). We are currently taking profit of the exceptional electron-withdrawing abilities of the TCBD group to tune the optoelectronic properties of some π-extended compounds (Chem. Eur. J. 2018, Chem. Commun. 2020Org. Lett. 2021).

Postdocs and students

- Matthieu Hicguet (PhD student, co-supervised with Fabienne Berrée)

- Clotilde Philippe (PhD student, co-supervised with Loïc Lemiègre)

- Alexandre Quelhas (PhD student, co-supervised with Jean-Claude Guillemin)

- Hervé Ruffin (Postdoc)

 

Publications

41) A. Quelhas, H. Gazzeh, T. Roisnel, Y. Trolez, J.-C. Guillemin, "Passerini and Ugi reactions involving kinetically unstable isocyanides", Eur. J. Org. Chem. 2021, accepted

40) N. Ripoche, M. Betou, C. Philippe, Y. Trolez, O. Mongin, M. Dudek, Z. Pokladek, K. Matczyszyn, M. Samoc, H. Sahnoune, J.-F. Halet, T. Roisnel, L. Toupet, M. Cordier, G. Moxey, M. G. Humphrey, F. Paul, "Two-photon absorption properties of multipolar triarylamino/tosylamido 1,1,4,4-tetracyanobutadienes", PhysChemChemPhys 2021, DOI: 10.1039/D1CP03346H

39) M. L. Zier, S. Colombel-Rouen, H. Ehrhorn, D. Bockfeld, Y. Trolez, M. Mauduit, M. Tamm, "Catalytic alkyne and diyne metathesis with mixed fluoroalkoxy-siloxy molybdenum alkylidyne complexes", Organometallics 2021, 40, 2008-2015

38) C. Philippe, A. T. Bui, S. Batsongo-Boulingui, Z. Pokladek, K. Matczyszyn, O. Mongin, L. Lemiègre, F. Paul, T. A. Hamlin, Y. Trolez, "1,1,4,4-Tetracyanobutadiene-functionalized anthracenes: regioselectivity of cycloadditions in the synthesis of small near-IR Dyes", Org. Lett. 2021, 23, 2007-2012 

37) I. Curbet, S. Colombel-Rouen, R. Manguin, A. Clermont, A. Quelhas, D. S. Müller, T. Roisnel, O. Baslé, Y. Trolez, M. Mauduit, "Expedient synthesis of conjugated triynes via alkyne metathesis", Chem. Sci. 202011, 4934-4938

36) A. T. Bui, C. Philippe, M. Beau, N. Richy, M. Cordier, T. Roisnel, L. Lemiègre, O. Mongin, F. Paul, Y. Trolez, "Synthesis, characterization, and unusual near-infrared luminescence of 1,1,4,4-tetracyanobutadiene derivatives", Chem. Commun. 2020, 56, 3571-3574

35) N. Kerisit, R. Ligny, E. S. Gauthier, J.-P. Guégan, L. Toupet, J.-C. Guillemin, Y. Trolez, "Synthesis and Reactivity of 5-Bromopenta-2,4-diynenitrile (BrC5N): an Access to π-Conjugated Scaffolds", Helv. Chim. Acta 2019, 102, e-1800232

34) Y. Trolez, "The Domino Hexadehydro-Diels-Alder Reaction: An Elegant Way toward Polyacenes, Chem 2018, 4, 2272-2274

33) R. Bouvier, R. Durand, L. Favereau, M. Srebro-Hooper, V. Dorcet, T. Roisnel, N. Vanthuyne, Y. Vesga, J. Donnelly, F. Hernandez, J. Autschbach, Y. Trolez, J. Crassous, "Helicenes Grafted with 1,1,4,4-Tetracyanobutadiene Moieties: p-Helical Push–Pull Systems with Strong Electronic Circular Dichroism and Two-Photon Absorption", Chem. Eur. J. 2018, 24, 14484-14494

32) Y. Trolez, A. D. Finke, F. Silvestri, F. Monti, B. Ventura, C. Boudon, J.-P. Gisselbrecht, W. B. Schweizer, J.-P. Sauvage, N. Armaroli, F. Diederich, "Unconventional Synthesis of a Cu(I)-Rotaxane With a Superacceptor Stopper: Ultrafast Excited-State Dynamics and Near-Infrared Luminescence", Chem. Eur. J. 2018, 24, 10422-10433

31) T. Duchanois, L. Liu, M. Pastore, A. Monari, C. Cebrián, Y. Trolez, M. Darari, K. Magra, A. Francés-Monerris, E. Domenichini, M. Beley, X. Assfeld, S. Haacke, P. C. Gros, "NHC-Based Iron Sensitizers for DSSCs", Inorganics 2018, 6, 63

30) S. Haberland, A. D. Finke, N. Kerisit, C. Katan, Y. Trolez, P. Gawel, I. Leito, M. Lokov, R. Järviste, K. Kaupmees, N. Trapp, L. Ruhlmann, C. Boudon, D. Himmel, F. Diederich, "Enhancement of Push–Pull Properties of Pentafulvene and Pentafulvalene Derivatives by Protonation at Carbon", Eur. J. Org. Chem. 2018, 739-749

29) R. Ligny, E. S. Gauthier, M. Yáñez, T. Roisnel, J.-C. Guillemin, Y. Trolez, "One-step synthesis of conjugated enynenitriles from bromocyanoacetylene", Org. Biomol. Chem. 2017, 15, 6050-6056

28) M. Betou, R. J. Durand, A. Sallustrau, C. Gousset, E. Le Coz, Y. R. Leroux, L. Toupet, E. Trzop, T. Roisnel, Y. Trolez, "Reactivity of Functionalized Ynamides with Tetracyanoethylene: Scope, Limitations and Optoelectronic Properties of the Adducts", Chem. Asian J. 201712, 1338-1346

27) B. Joalland, N. Jamal-Eddine, J. Klos, F. Lique, Y. Trolez, J.-C. Guillemin, S. Carles, L. Biennier, "On the Low-Temperature Reactivity of C2n+1N- Anions with Polar Molecules", J. Phys. Chem. Lett. 20167, 2957-2961

26) U. Szczepaniak, M. Turowski, T. Custer, M. Gronowski, N. Kerisit, Y. Trolez, R. Kołos, "Infrared and Raman spectroscopy of methylcyanodiacetylene (CH3C5N), ChemPhysChem 2016, 17, 3047-3054

25) Z. Pokladek, N. Ripoche, M. Betou, Y. Trolez, O. Mongin, J. Olesiak-Banska, K. Matczyszyn, M. Samoc, M. G. Humphrey, M. Blanchard-Desce, F. Paul, "Linear Optical and Third-Order Nonlinear Optical Properties of some Fluorenyl- and Triarylamine-Containing Tetracyano-butadiene Derivatives", Chem. Eur. J. 2016, 22, 10155-10167

24) N. Kerisit, C. Rouxel, S. Colombel-Rouen, L. Toupet, J.-C. Guillemin, Y. Trolez, "Synthesis, Chemistry, and Photochemistry of Methylcyanobutadiyne in the Context of Space Science", J. Org. Chem. 2016, 81, 3560-3567

23) M. M. Montero-Campillo, O. Mó, M. Yáñez, A. Benidar, C. Rouxel, N. Kerisit, Y. Trolez, J.-C. Guillemin, "Gas Phase Infrared Spectroscopy of Substituted Cyanobutadiynes.The Role Played by Bromine Atom and Methyl Group as Substituents.", ChemPhysChem 2016, 17, 1018-1024

22) M. Betou, A. Sallustrau, L. Toupet, Y. Trolez, "Synthesis of conjugated multi-ynamides by copper-catalyzed reaction", Tetrahedron Lett. 2015, 56, 4627-4630

21) N. Kerisit, A. D. Finke, N. Trapp, Y. R. Leroux, J.-C. Guillemin, Y. Trolez, F. Diederich, “New reactivity of 6,6-bis-donor-substituted pentafulvenes: one-step synthesis of highly substituted [3]cumulene and dihydropentalene”, Tetrahedron 2015, 71, 4393-4399

20) N. Kerisit, L. Toupet, P. Larini, L. Perrin, J.-C. Guillemin, Y. Trolez, “Straightforward Synthesis of 5-Bromopenta-2,4-diynenitrile and Its Reactivity Towards Terminal Alkynes: A Direct Access to Diene and Benzofulvene Scaffolds”, Chem. Eur. J. 2015, 21, 6042-6047

19) M. Betou, N. Kerisit, E. Meledje, Y. R. Leroux, C. Katan, J.-F. Halet, J.-C. Guillemin, Y. Trolez, "High-yield formation of substituted tetracyanobutadienes from reaction of ynamides with tetracyanoethylene", Chem. Eur. J. 2014, 20, 9553-9557

18) V. Heitz, J.-P. Sauvage, Y. Trolez, "Cu(I)/Zn2+exchange has no geometrical effect in a cyclic [4]rotaxane whereas it induces rearrangement in a simpler [3]rotaxane", Inorg. Chim. Acta 2014, 417186-191

17) S.Carles, Y. Trolez, J.-C. Guillemin, H. Mollendal,"Rotational spectrum of 4-methylcyanoallene (CH3CH=C=CH-CN), a chiral molecule of potential astrochemical interest", Astronomy and Astrophysics 2014, 564, A82

16) F. Durola, V. Heitz, F. Reviriego, C. Roche, J.-P. Sauvage, A. Sour, Y. Trolez, "Cyclic [4]rotaxanes containing two parallel porphyrinic plates : towards switchable molecular receptors and compressors", Acc. Chem. Res. 201447, 633-645

15) N. Kerisit, L. Toupet, Y. Trolez, J.-C. Guillemin, "Methylcyanobutadiyne: Synthesis, X-ray structure and photochemistry; towards an explanation of its formation in the Interstellar Medium", Chem. Eur. J. 2013, 19, 17683-17686

14) A. Joosten, Y. Trolez, V. Heitz, J.-P. Sauvage, "Use of cleavable coordinating rings as protective groups in the synthesis of a rotaxane whose axis incorporates more chelating groups than threaded macrocycles", Chem. Eur. J. 2013, 19, 12815-12823

13) B. Ventura, L. Flamigni, J.-P. Collin, F. Durola, V. Heitz, F. Reviriego, J.-P. Sauvage, Y. Trolez, "NIR emission of cyclic [4]rotaxanes containing p-extended porphyrin chromophores", Phys. Chem. Chem. Phys. 2012, 14, 10589-10594

12) A. Joosten, Y. Trolez, J.-P. Collin, V. Heitz, J.-P. Sauvage, "A copper(I)-assembled [3]rotaxane whose two rings act as flapping wings", J. Am. Chem. Soc. 2012, 134, 1802-1809

11) F. Durola, S. Durot, V. Heitz, A. Joosten, J.-P. Sauvage, Y. Trolez, "Formation of copper(I)-templated [2]rotaxanes using ‘‘click’’ methodology: influence of the base, the thread and the catalyst", J. Incl. Phenom. Macrocycl. Chem. 2011, 71, 507-515

10) J.-P. Collin, S. Durot, J.-P. Sauvage, Y. Trolez, "Synthesis of [2]-, [3]-, and [4]rotaxanes whose axis contains two bidentate and two tridentate chelates", New. J. Chem. 2011, 35, 2009-2012

9) J.-P. Sauvage, Y. Trolez, D. Canevet, M. Sallé, "Intercalation of tetrathiafulvalene between the two plates of a copper(I)-complexed [4]rotaxane", Eur. J. Org. Chem. 2011, 2413-2416

8) J.-P. Collin, S. Durot, M. Keller, J.-P. Sauvage, Y. Trolez, M. Cetina and K. Rissanen, "Synthesis of [5]Rotaxanes Containing Bi- and Tridentate Coordination Sites in the Axis", Chem. Eur. J. 201117, 947-957

7) J.-P. Collin, F. Durola, V. Heitz, F. Reviriego, J.-P. Sauvage, Y. Trolez, "A cyclic[4]rotaxane which behaves as a switchablemolecular receptor : copper complexation-driven formation of a rigid scaffold from a collapsed structure", Angew. Chem. Int. Ed. 2010, 49, 10172-10175

6) J.-P. Collin, F. Durola, J. Frey, V. Heitz, F. Reviriego, J.-P. Sauvage, Y. Trolez, K. Rissanen, "Templated synthesis of cyclic [4]rotaxanes consisting of two stiff rods threaded through two bis-macrocycles with a large and rigid central plate as spacer", J. Am. Chem. Soc. 2010132, 6840-6850

5) J.-P. Collin, J.-P. Sauvage, Y. Trolez, K. Rissanen, "[3]Rotaxanes and [3]pseudorotaxanes with a rigid two-bidentate chelate axle threaded through two coordinating rings", New. J. Chem. 2009, 33, 2148-2154

4) J.-P. Collin, F. Durola, J. Frey, V. Heitz, J.-P. Sauvage, C. Tock, Y. Trolez, "Quantitative formation of [4]pseudorotaxanes from two rods and two bis-macrocycles incorporating porphyrinic plates between the rings", Chem. Commun. 2009, 1706-1708

3) J.-C. Guillemin, Y. Trolez, A. Moncomble, "Synthesis, chemistry and photochemistry of cyanobutadiyne (HCC-CC-CN)", Adv. in Space Res. 2008, 42, 2002-2007

2) Y. Bénilan, A. Jolly, Y. Trolez, F. Raulin, J.-C. Guillemin, "Infrared band intensities of cyanobutadiyne (HC5N) between 400 and 4000 cm-1", J. Mol. Spectrosc. 2007, 245, 109-114

1) Y. Trolez, J.-C. Guillemin, "Synthesis and Characterization of 2,4-Pentadiynenitrile—A Key Compound in Space Science", Angew. Chem. Int. Ed. 2005, 44, 7224-7226

 

Publications referenced in HAL :