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

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...

Full description

Bibliographic Details
Main Authors: Arthur H. G. David, Sandra Míguez-Lago, Carlos M. Cruz, Juan M. Cuerva, Victor Blanco, Araceli G. Campaña
Format: Article
Language:English
Published: Georg Thieme Verlag 2021-01-01
Series:Organic Materials
Subjects:
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1722848
_version_ 1819174975804801024
author Arthur H. G. David
Sandra Míguez-Lago
Carlos M. Cruz
Juan M. Cuerva
Victor Blanco
Araceli G. Campaña
author_facet Arthur H. G. David
Sandra Míguez-Lago
Carlos M. Cruz
Juan M. Cuerva
Victor Blanco
Araceli G. Campaña
author_sort Arthur H. G. David
collection DOAJ
description 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.
first_indexed 2024-12-22T20:47:31Z
format Article
id doaj.art-c880afe40c4944958e806499b56e9729
institution Directory Open Access Journal
issn 2625-1825
language English
last_indexed 2024-12-22T20:47:31Z
publishDate 2021-01-01
publisher Georg Thieme Verlag
record_format Article
series Organic Materials
spelling doaj.art-c880afe40c4944958e806499b56e97292022-12-21T18:13:11ZengGeorg Thieme VerlagOrganic Materials2625-18252021-01-01030105105910.1055/s-0041-1722848Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and FullerenesArthur H. G. David0Sandra Míguez-Lago1Carlos M. Cruz2Juan M. Cuerva3Victor Blanco4Araceli G. Campaña5Department of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, SpainDepartment of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, SpainDepartment of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, SpainDepartment of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, SpainDepartment of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, SpainDepartment of Organic Chemistry, Faculty of Sciences, University of Granada. Avda. Fuente Nueva S/N, 18071, Granada, SpainAbstract 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.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1722848nanographenescontorted aromaticssupramolecular chemistryhost–guest systemsheptacyclic polyarenesmolecular recognition
spellingShingle Arthur H. G. David
Sandra Míguez-Lago
Carlos M. Cruz
Juan M. Cuerva
Victor Blanco
Araceli G. Campaña
Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes
Organic Materials
nanographenes
contorted aromatics
supramolecular chemistry
host–guest systems
heptacyclic polyarenes
molecular recognition
title Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes
title_full Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes
title_fullStr Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes
title_full_unstemmed Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes
title_short Heptagon-Containing Saddle-Shaped Nanographenes: Self-Association and Complexation Studies with Polycyclic Aromatic Hydrocarbons and Fullerenes
title_sort heptagon containing saddle shaped nanographenes self association and complexation studies with polycyclic aromatic hydrocarbons and fullerenes
topic nanographenes
contorted aromatics
supramolecular chemistry
host–guest systems
heptacyclic polyarenes
molecular recognition
url http://www.thieme-connect.de/DOI/DOI?10.1055/s-0041-1722848
work_keys_str_mv AT arthurhgdavid heptagoncontainingsaddleshapednanographenesselfassociationandcomplexationstudieswithpolycyclicaromatichydrocarbonsandfullerenes
AT sandramiguezlago heptagoncontainingsaddleshapednanographenesselfassociationandcomplexationstudieswithpolycyclicaromatichydrocarbonsandfullerenes
AT carlosmcruz heptagoncontainingsaddleshapednanographenesselfassociationandcomplexationstudieswithpolycyclicaromatichydrocarbonsandfullerenes
AT juanmcuerva heptagoncontainingsaddleshapednanographenesselfassociationandcomplexationstudieswithpolycyclicaromatichydrocarbonsandfullerenes
AT victorblanco heptagoncontainingsaddleshapednanographenesselfassociationandcomplexationstudieswithpolycyclicaromatichydrocarbonsandfullerenes
AT araceligcampana heptagoncontainingsaddleshapednanographenesselfassociationandcomplexationstudieswithpolycyclicaromatichydrocarbonsandfullerenes