ABSTRACT Polycyclic aromatic hydrocarbons (PAHs) show promise for applications in functional devices such as organic photovoltaics and field-effect transistors, but, although nanometre-sized

PAHs—often referred to as nanographenes—have been well investigated as single-layer molecules, their multilayer counterparts remain rather unexplored. Here we show the assembly of a C64

nanographene derivative (comprising a planar core decorated with four _meta_-terphenyl–imide moieties at its periphery) into multilayer stacks with smaller PAHs ranging from naphthalene to

ovalene and hexabenzocoronene. The functionalized C64 nanographene serves as a ditopic host that can accommodate a smaller PAH on either side of its planar core, in cavities delimited by its

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PARALLEL-STACKED AROMATIC MOLECULES IN HYDROGEN-BONDED INORGANIC FRAMEWORKS Article Open access 10 December 2021 MOIRÉ TWO-DIMENSIONAL COVALENT ORGANIC FRAMEWORK SUPERLATTICES Article Open

access 20 February 2025 BANDGAP ENGINEERING OF TWO-DIMENSIONAL C3N BILAYERS Article 28 June 2021 DATA AVAILABILITY Crystallographic data for the structures in this Article have been

deposited at the Cambridge Crystallographic Data Centre under deposition nos. CCDC 2068629 (monolayer, 1), 2068630 (multilayer, [COR·1·COR]_n_), 2068631 (hexalayer, [COR·1·COR]2) and 2068632

(tetralayer, [COR·1·1·COR]). Copies of data can be obtained free of charge from www.ccdc.cam.ac.uk/structures/. Details of the synthesis and crystallographic analyses, UV–vis and

fluorescence spectra, traces of cyclic and differential pulse voltammetry, plots of NMR titration and variable-temperature NMR experiments, DOSY NMR spectra, traces of ITC experiments and a

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(2015). Article  CAS  Google Scholar  Download references ACKNOWLEDGEMENTS We thank the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) for financial support (grant no. WU

317/20-2). AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany Magnus Mahl, M. A. Niyas, Kazutaka Shoyama & Frank

Würthner * Center for Nanosystems Chemistry (CNC), Universität Würzburg, Würzburg, Germany Kazutaka Shoyama & Frank Würthner Authors * Magnus Mahl View author publications You can also

search for this author inPubMed Google Scholar * M. A. Niyas View author publications You can also search for this author inPubMed Google Scholar * Kazutaka Shoyama View author publications

You can also search for this author inPubMed Google Scholar * Frank Würthner View author publications You can also search for this author inPubMed Google Scholar CONTRIBUTIONS F.W. initiated

and supervised the entire work. M.M. performed the synthesis and complexation experiments. M.M. and M.A.N. grew the single crystals for crystallographic analysis. K.S. conducted the

crystallographic measurements and analysis. M.A.N. and K.S. conducted the DFT calculations. All authors contributed to writing the manuscript. CORRESPONDING AUTHOR Correspondence to Frank

Würthner. ETHICS DECLARATIONS COMPETING INTERESTS The authors declare no competing interests. PEER REVIEW PEER REVIEW INFORMATION _Nature Chemistry_ thanks the anonymous reviewers for their

contribution to the peer review of this work. ADDITIONAL INFORMATION PUBLISHER’S NOTE Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional

affiliations. SUPPLEMENTARY INFORMATION SUPPLEMENTARY INFORMATION Details of synthesis, crystallographic analysis and computation. Supplementary Figs. 1–22 and Tables 1–15. SUPPLEMENTARY

DATA 1 Crystal structure of monolayer 1; CCDC 2068629. SUPPLEMENTARY DATA 2 Crystal structure of polylayer _(COR-1-COR)n; CCDC 2068630. SUPPLEMENTARY DATA 3 Crystal structure of hexalayer

(COR-1-COR)2; CCDC 2068631. SUPPLEMENTARY DATA 4 Crystal structure of tetralayer COR-1-1-COR; CCDC 2068632. SUPPLEMENTARY SOURCE DATA 1 Source Data Supplementary Figs. 7, 11a–d, 12a–c,

13b–d, 14a–c and 15. Fit of proton-signals from a 1H NMR titration experiment. Fit of UV–vis titration experiments of nanographene 1 in chloroform solutions. Fit of fluorescence titration

experiments of nanographene 1 in chloroform solutions. Comparison of the average Gibbs free energies from UV–vis and fluorescence titration experiments with different guest molecules. SOURCE

DATA SOURCE DATA FIG. 4 Computed values of interaction energies from ALMO-EDA. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Mahl, M., Niyas, M.A.,

Shoyama, K. _et al._ Multilayer stacks of polycyclic aromatic hydrocarbons. _Nat. Chem._ 14, 457–462 (2022). https://doi.org/10.1038/s41557-021-00861-5 Download citation * Received: 11 March

2021 * Accepted: 19 November 2021 * Published: 07 February 2022 * Issue Date: April 2022 * DOI: https://doi.org/10.1038/s41557-021-00861-5 SHARE THIS ARTICLE Anyone you share the following

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