Helical bilayer nanographenes (HBNGs) are chiral π-extended aromatic compounds consisting of two π-π stacked hexabenzocoronenes (HBCs) joined by a helicene, thus resembling van der Waals layered 2D materials. Herein, we compare [9]HBNG, [10]HBNG, and [11]HBNG helical bilayers endowed with [9], [10], and [11]helicenes embedded in their structure, respectively. Interestingly, the helicene length defines the overlapping degree between the two HBCs (number of benzene rings involved in π-π interactions between the two layers), being 26, 14, and 10 benzene rings, respectively, according to the X-ray analysis. Unexpectedly, the electrochemical study shows that the lesser π-extended system [9]HBNG shows the strongest electron donor character, in part by interlayer exchange resonance, and more red-shifted values of emission. Furthermore, [9]HBNG also shows exceptional chiroptical properties with the biggest values of gabs and glum (3.6 × 10-2) when compared to [10]HBNG and [11]HBNG owing to the fine alignment in the configuration of [9]HBNG between its electric and magnetic dipole transition moments. Furthermore, spectroelectrochemical studies as well as the fluorescence spectroscopy support the aforementioned experimental findings, thus confirming the strong impact of the helicene length on the properties of this new family of bilayer nanographenes.

Departament of Physical Chemistry Facultad de Ciencias Universidad de Málaga 29071 Málaga Spain

Departamento de Química Orgánica 1 Facultad de Ciencias Químicas Universidad Complutense de Madrid 28040 Madrid Spain

Department of Physics and Astronomy University of Sheffield S3 7RH Sheffield U K

IMDEA Nanociencia C Faraday 9 Campus de Cantoblanco 28049 Madrid Spain

Institut des Sciences Chimiques de Rennes UMR 6226 CNRS─Univ Rennes 35000 Rennes France

Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nám 2 166 10 Prague 6 Czech Republic

Laboratorio DRX Monocristal SIdI Universidad Autónoma de Madrid 28049 Madrid Spain

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