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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(01): 051-059
DOI: 10.1055/s-0041-1722848
Focus Issue: Curved Organic π-Systems
Original Article

Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes

Arthur H. G. David 
a   Department of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, Spain
,
Sandra Míguez-Lago 
a   Department of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, Spain
,
Carlos M. Cruz 
a   Department of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, Spain
,
Juan M. Cuerva 
a   Department of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, Spain
,
Victor Blanco 
a   Department of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, Spain
,
Araceli G. Campaña 
a   Department of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, Spain
› Institutsangaben Funding Information We acknowledge FEDER/Junta de Andalucía (A-FQM-339-UGR18, Programa Operativo FEDER 2014-2020, Consejería de Economía y Conocimiento), the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program (ERC-2015-STG-677023), and Ministerio de Ciencia, Innovación y Universidades (MICIU/FEDER/AEI, Spain; PGC2018-101181-B-I00) for financial support.
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Abstract

Supramolecular interactions between molecules of the same or different nature determine to a great extent the degree of their applicability in many fields of science. To this regard, planar polycyclic aromatic hydrocarbons (PAHs) and their nanometric congeners, nanographenes (NGs), as well as positively curved ones, as for instance corannulene, have been extensively explored. However, negatively curved saddle-shaped NGs have remained a curiosity to date within this field. Therefore, here we communicate the first systematic study on the supramolecular behavior of heptagon-containing hexa-peri-hexabenzocoronene analogues. Thus, their self-association and host–guest complexation processes with both flat and curved PAHs, and fullerenes have been studied by means of 1H and 13C NMR titrations in solution, identifying C70 as one of the guests with the highest association constant among all the ones tested.

Key words

nanographenes - contorted aromatics - supramolecular chemistry - host–guest systems - heptacyclic polyarenes - molecular recognition

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/s-0041-1722848.


Supporting Information



Publikationsverlauf

Eingereicht: 16. Oktober 2020

Angenommen: 14. Dezember 2020

Artikel online veröffentlicht:
08. Februar 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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