Weakly Self-Assembled [6]Helicenes: Circularly Polarized Light and Spin Filtering Properties.

chiral induced spin selectivity circularly polarized luminescence helicenes spin polarization supramolecular assemblies

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
13 Nov 2023
Historique:
received: 14 07 2023
medline: 28 8 2023
pubmed: 28 8 2023
entrez: 27 8 2023
Statut: ppublish

Résumé

Self-assembling features, chiroptical activity, and spin filtering properties are reported for 2,15- and 4,13-disubstituted [6]helicenes decorated in their periphery with 3,4,5-tris(dodecyloxy)-N-(4-ethynylphenyl)benzamide moieties. The weak non-covalent interaction between these units conditions the corresponding circularly polarized luminescence and spin polarization. The self-assembly is overall weak for these [6]helicene derivatives that, despite the formation of H-bonding interactions between the amide groups present in the peripheral moieties, shows very similar chiroptical properties both in the monomeric or aggregated states. This effect could be explained by considering the steric effect that these groups could generate in the growing of the corresponding aggregate formed. Importantly, the self-assembling features also condition chiral induced spin selectivity (CISS effect), with experimental spin polarization (SP) values found between 35-40 % for both systems, as measured by magnetic-conducting atomic force microscopy (AFM) technique.

Identifiants

pubmed: 37635073
doi: 10.1002/chem.202302254
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202302254

Subventions

Organisme : Ministerio de Ciencia e Innovación
ID : PID2020-113512GB-I00
Organisme : Ministerio de Ciencia e Innovación
ID : TED2021-130285B-I00
Organisme : Xunta de Galicia
Organisme : Israeli Ministry for Science and Technology
Organisme : H2020 European Research Council
ID : 859752

Informations de copyright

© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Références

 
J. Crassous, I. G. Stará, I. Starý, Helicenes - Synthesis, Properties and Applications, Wiley, 2022;
C.-F. Chen, Y. Shen, in Helicene Chemistry: From Synthesis to Applications, Springer: Berlin, Heidelberg, 2017;
M. Gingras, Chem. Soc. Rev. 2013, 42, 968-1006;
M. Gingras, G. Felix, R. Peresutti, Chem. Soc. Rev. 2013, 42, 1007-1050;
Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463-1535;
K. Dhbaibi, L. Favereau, J. Crassous, Chem. Rev. 2019, 119, 8846-8953.
 
K. Dhbaibi, L. Abella, S. Meunier-Della-Gatta, T. Roisnel, N. Vanthuyne, B. Jamoussi, G. Pieters, B. Racine, E. Quesnel, J. Autschbach, J. Crassous, L. Favereau, Chem. Sci. 2021, 12, 5522-5533;
M. J. Narcis, N. Takenaka, Eur. J. Org. Chem. 2014, 21-34;
D. Schweinfurth, M. Zalibera, M. Kathan, C. Shen, M. Mazzolini, N. Trapp, J. Crassous, G. Gescheidt, F. Diederich, J. Am. Chem. Soc. 2014, 136, 13045-13052;
E. Anger, M. Srebro, N. Vanthuyne, L. Toupet, S. Rigaut, C. Roussel, J. Autschbach, J. Crassous, R. Réau, J. Am. Chem. Soc. 2012, 134, 15628-15631;
T. Verbiest, S. V. Elshocht, M. Kauranen, L. Hellemans, J. Snauwaert, C. Nuckolls, T. J. Katz, A. Persoons, Science 1998, 282, 913-915.
 
V. Kiran, S. P. Mathew, S. R. Cohen, I. Hernández Delgado, J. Lacour, R. Naaman, Adv. Mater. 2016, 28, 1957-1962;
M. Kettner, V. Maslyuk, D. Ngrenberg, J. Seibel, R. Gutierrez, G. Cuniberti, K.-H. Ernst, H. Zacharias, J. Phys. Chem. Lett. 2018, 9, 2025-2030;
T.-R. Pan, A.-M. Guo, Q.-F. Sun, Phys. Rev. B: Condens. Matter Mater. Phys. 2016, 94, 235448;
A. M. García, C. Martínez, A. Ruiz-Carretero, Front. Chem. 2021, 9, 722727;
Y. Liang, K. Banjac, K. Martin, N. Zigon, S. Lee, N. Vanthuyne, F. A. Garcés-Pineda, J. R. Galán-Mascarós, X. Hu, N. Avarvari, M. Lingenfelder, Nat. Commun. 2022, 13, 3356.
 
E. S. Gauthier, R. Rodríguez, J. Crassous, Angew. Chem. Int. Ed. 2020, 59, 22840-22856;
B. Doisteau, J.-R. Jiménez, C. Piguet, Front. Chem. 2020, 8, 555;
K. Staszak, K. Wieszczycka, V. Marturano, B. Tylkowski, Coord. Chem. Rev. 2019, 397, 76-90;
R. Carr, N. H. Evans, D. Parker, Chem. Soc. Rev. 2012, 41, 7673-7686.
 
S. Liu, F. Li, Y. X. Wang, X. J. Li, C. J. Zhu, Y. X. Cheng, J. Mater. Chem. C 2017, 5, 6030-6036;
E. M. Sánchez-Carnerero, F. Moreno, B. L. Maroto, A. R. Agarrabeitia, M. J. Ortiz, B. G. Vo, G. Muller, S. de la Moya, J. Am. Chem. Soc. 2014, 136, 3346-3349;
Y. Haketa, Y. Bando, K. Takaishi, M. Uchiyama, A. Muranaka, M. Naito, H. Shibaguchi, T. Kawai, H. Maeda, Angew. Chem. Int. Ed. 2012, 51, 7967-7971;
Angew. Chem. 2012, 124, 8091-8095.
M. A. Medel, R. Tapia, V. Blanco, D. Miguel, S. P. Morcillo, A. G. Campaña, Angew. Chem. Int. Ed. 2021, 60, 6094-6100;
Angew. Chem. 2021, 133, 6159-6165.
J. Crassous, M. Fuchter, D. Freedman, N. Kotov, J. Moon, M. Beard, S. Feldmann, Nat. Rev. Mater. 2023, 8, 365-371.
 
A. R. A. Palmans, E. W. Meijer, Angew. Chem. Int. Ed. 2007, 46, 8948-8968;
Angew. Chem. 2007, 119, 9106-9126;
Y. Dorca, E. E. Greciano, J. S. Valera, R. Gómez, L. Sánchez, Chem. Eur. J. 2019, 25, 5848-5864.
C. Kulkarni, E. W. Meijer, A. R. A. Palmans, Acc. Chem. Res. 2017, 50, 1928-1936.
 
S. Ghosh, X.-Q. Li, V. Stepanenko, F. Würthner, Chem. Eur. J. 2008, 14, 11343-11357;
M. A. Martínez, A. Doncel-Giménez, J. Cerdá, J. Calbo, R. Rodríguez, J. Aragó, J. Crassous, E. Ortí, L. Sánchez, J. Am. Chem. Soc. 2021, 143, 13281-13291;
S. van Cleuvenbergen, P. Kedziora, J.-L. Fillaut, T. Verbiest, K. Clays, H. Akdas-Kilig, F. Camerel, Angew. Chem. Int. Ed. 2017, 56, 9546-9550;
Angew. Chem. 2017, 129, 9674-9678.
 
E. E. Greciano, J. Calbo, J. Buendía, J. Cerdá, J. Aragó, E. Ortí, L. Sánchez, J. Am. Chem. Soc. 2019, 141, 7463-7472;
F. García, L. Sánchez, J. Am. Chem. Soc. 2012, 134, 734-742.
 
N. Sasaki, M. F. J. Mabesoone, J. Kikkawa, T. Fukui, N. Shioya, T. Shimoaka, T. Hasegawa, H. Takagi, R. Haruki, N. Shimizu, S. Adachi, E. W. Meijer, M. Takeuchi, K. Sugiyasu, Nat. Commun. 2020, 11, 1-9;
M. F. J. Mabesoone, A. J. Markvoort, M. Banno, T. Yamaguchi, F. Helmich, Y. Naito, E. Yashima, A. R. A. Palmans, E. W. Meijer, J. Am. Chem. Soc. 2018, 140, 7810-7819.
M. M. J. Smulders, P. J. M. Stals, T. Mes, T. F. E. Paffen, A. P. H. J. Schenning, A. R. A. Palmans, E. W. Meijer, J. Am. Chem. Soc. 2010, 132, 620-626.
M. L. Ślęczkowski, M. F. J. Mabesoone, P. Ślęczkowski, A. R. A. Palmans, E. W. Meijer, Nat. Chem. 2021, 13, 200-207.
 
J. S. Kang, S. Kang, J. M. Suh, S. M. Park, D. K. Yoon, M. H. Lim, W. Y. Kim, M. Seo, J. Am. Chem. Soc. 2022, 144, 2657-2666;
E. E. Greciano, R. Rodríguez, K. Maeda, L. Sánchez, Chem. Commun. 2020, 56, 2244-2247;
J. Kim, J. Lee, W. Y. Kim, H. Kim, S. Lee, H. C. Lee, Y. S. Lee, M. Seo, S. Y. Kim, Nat. Commun. 2015, 6, 6959.
 
Z. Xie, V. Stepanenko, K. Radacki, F. Würthner, Chem. Eur. J. 2012, 18, 7060-7070;
J. Buendía, E. E. Greciano, L. Sánchez, J. Org. Chem. 2015, 80, 12444-12452.
 
K. E. S. Phillips, T. J. Katz, S. Jockusch, A. J. Lovinger, N. J. Turro, J. Am. Chem. Soc. 2001, 123, 11899-11907;
T. Kaseyama, S. Furumi, X. Zhang, K. Tanaka, M. Takeuchi, Angew. Chem. Int. Ed. 2011, 50, 3684-3687;
Angew. Chem. 2011, 123, 3768-3771;
J. S. Valera, R. Gómez, L. Sánchez, Org. Lett. 2018, 20, 2020-2023; for a review on supramolecular assemblies of chiral molecules devoid of chiral centers see:
W. R. Henderson, R. K. Castellano, Polym. Int. 2021, 70, 897-910.
R. Rodríguez, C. Naranjo, A. Kumar, P. Matozzo, T. Kumar Das, Q. Zhu, N. Vanthuyne, R. Gómez, R. Naaman, L. Sánchez, J. Crassous, J. Am. Chem. Soc. 2022, 144, 7709-7719.
Y. Dorca, C. Naranjo, G. Ghosh, B. Soberats, J. Calbo, E. Ortí, G. Fernández, L. Sánchez, Chem. Sci. 2022, 13, 81-89.
 
E. Anger, M. Srebro, N. Vanthuyne, L. Toupet, S. Rigaut, C. Roussel, J. Autschbach, J. Crassous, R. Réau, J. Am. Chem. Soc. 2012, 134, 15628-15631;
C. Shen, F. Gan, G. Zhang, Y. Ding, J. Wang, R. Wang, J. Crassous, H. Qiu, Mater. Chem. Front. 2020, 4, 837-844.
F. Wang, M. A. J. Gillissen, P. J. M. Stals, A. R. A. Palmans, E. W. Meijer, Chem. Eur. J. 2012, 18, 11761-11770.
S. Diring, F. Camerel, B. Donnio, T. Dintzer, S. Toffanin, R. Capelli, M. Muccini, R. Ziessel, J. Am. Chem. Soc. 2009, 131, 18177-18185.
 
M. Wehner, M. I. S. Röhr, M. Bühler, V. Stepanenko, W. Wagner, F. Würthner, J. Am. Chem. Soc. 2019, 141, 6092-6107;
D. S. Philips, K. K. Kartha, A. T. Politi, T. Krüger, R. Q. Albuquerque, G. Fernández, Angew. Chem. Int. Ed. 2019, 58, 4732-4736;
Angew. Chem. 2019, 131, 4782-4787;
E. E. Greciano, S. Alsina, G. Ghosh, G. Fernández, L. Sánchez, Small Methods 2020, 4, 1900715.
R. van der Weegen, P. A. Korevaar, P. Voudouris, I. K. Voets, T. F. A. de Greef, J. A. J. M. Vekemans, E. W. Meijer, Chem. Commun. 2013, 49, 5532-5534.
K. Dhbaibi, M. Grasser, H. Douib, V. Dorcet, O. Cador, N. Vanthuyne, F. Riobé, O. Maury, S. Guy, A. Bensalah-Ledoux, B. Baguenard, G. L. J. A Rikken, C. Train, B. Le Guennic, F. Pointillart, M. Atzori, J. Crassous, Angew. Chem. Int. Ed. 2023, 62, e202215558;
Angew. Chem. 2023, 135, e202215558.
P. A. Korevaar, C. Schaefer, T. F. A. de Greef, E. W. Meijer, J. Am. Chem. Soc. 2012, 134, 13482-13491.
 
K. Banerjee-Ghosh, O. Ben Dor, F. Tassinari, E. Capua, S. Yochelis, A. Capua, S.-H. Yang, S. S. P. Parkin, S. Sarkar, L. Kronik, L. T. Baczewski, R. Naaman, Y. Paltiel, Science 2018, 360, 1331-1334;
R. Naaman, Y. Paltiel, D. H. Waldeck, Nat. Chem. Rev. 2019, 3, 250-260;
Y.-H. Kim, Y. Zhai, H. Lu, X. Pan, C. Xiao, E. A. Gaulding, S. P. Harvey, J. J. Berry, Z. V. Vardeny, J. M. Luther, C. M. Beard, Science 2021, 371, 1129-1133;
H. Lu, J. Wang, C. Xiao, X. Pan, X. Chen, R. Brunecky, J. J. Berry, K. Zhu, M. C. Beard, Z. V. Vardeny, Sci. Adv. 2019, 5, No. eaay0571.
 
Y. Sang, Q. Zhu, X. Zhou, Y. Jiang, M. Liu, Angew. Chem. Int. Ed. 2023, DOI:10.1002/anie.202215867;
A. K. Mondal, N. Brown, S. Mishra, P. Makam, D. Wing, S. Gilead, Y. Wiesenfeld, G. Leitus, L. J. W. Shimon, R. Carmieli, D. Ehre, G. Kamieniarz, J. Fransson, O. Hod, L. Kronik, E. Gazit, R. Naaman, ACS Nano 2020, 14, 16624;
S. Mishra, A. K. Mondal, S. Pal, T. K. Das, E. Z. B. Smolinsky, G. Siligardi, R. Naaman, J. Phys. Chem. C 2020, 124, 10776;
A. Kumar Mondal, M. D. Preuss, M. L. Ślęczkowski, T. Kumar Das, G. Vantomme, E. W. Meijer, R. Naaman, J. Am. Chem. Soc. 2021, 143, 7189-7195.
 
J. Fransson, Phys. Rev. B 2020, 102, 235416;
T. K. Das, F. Tassinari, R. Naaman, J. Fransson, J. Phys. Chem. C 2022, 126, 3257-3264.
D. Amsallem, A. Kumar, R. Naaman, O. Gidron, Chirality 2023, 35, 562-568.
A. U. Malik, F. Gan, C. Shen, N. Yu, R. Wang, J. Crassous, M. Shu, H. Qiu, J. Am. Chem. Soc. 2018, 140, 2769-2772.
K. Dhbaibi, L. Favereau, M. Srebro-Hooper, C. Quinton, N. Vanthuyne, L. Arrico, T. Roisnel, B. Jamoussi, C. Poriel, C. Cabanetos, J. Autschbach, J. Crassous, Chem. Sci. 2020, 22, 567-576.

Auteurs

Rafael Rodríguez (R)

Institut des Sciences Chimiques de Rennes, University of Rennes, CNRS, ISCR, UMR 6226, F-35000, Rennes, France.

Cristina Naranjo (C)

Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040, Madrid, Spain.

Anil Kumar (A)

Department of Chemical and Biological Physics, Weizmann Institute of Science, Rehovot, 76100, Israel.

Kais Dhbaibi (K)

Institut des Sciences Chimiques de Rennes, University of Rennes, CNRS, ISCR, UMR 6226, F-35000, Rennes, France.

Paola Matozzo (P)

Institut des Sciences Chimiques de Rennes, University of Rennes, CNRS, ISCR, UMR 6226, F-35000, Rennes, France.

Franck Camerel (F)

Institut des Sciences Chimiques de Rennes, University of Rennes, CNRS, ISCR, UMR 6226, F-35000, Rennes, France.

Nicolas Vanthuyne (N)

Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313, Marseille, 13397, France.

Rafael Gómez (R)

Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040, Madrid, Spain.

Ron Naaman (R)

Department of Chemical and Biological Physics, Weizmann Institute of Science, Rehovot, 76100, Israel.

Luis Sánchez (L)

Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040, Madrid, Spain.

Jeanne Crassous (J)

Institut des Sciences Chimiques de Rennes, University of Rennes, CNRS, ISCR, UMR 6226, F-35000, Rennes, France.

Classifications MeSH