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

Author:

Rodríguez Rafael1ORCID,Naranjo Cristina2,Kumar Anil3,Dhbaibi Kais1,Matozzo Paola1,Camerel Franck1ORCID,Vanthuyne Nicolas4ORCID,Gómez Rafael2ORCID,Naaman Ron3ORCID,Sánchez Luis2ORCID,Crassous Jeanne1ORCID

Affiliation:

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

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

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

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

Abstract

AbstractSelf‐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.

Funder

Ministerio de Ciencia e Innovación

Xunta de Galicia

H2020 European Research Council

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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