Self-Assembly of bowl-shaped naphthalimide-annulated corannulene

Please always quote using this URN: urn:nbn:de:bvb:20-opus-204396
  • The self-assembly of a bowl-shaped naphthalimide-annulated corannulene of high solubility has been studied in a variety of solvents by NMR and UV/Vis spectroscopy. Evaluation by the anti-cooperative K\(_2\)-K model revealed the formation of supramolecular dimers of outstanding thermodynamic stability. Further structural proof for the almost exclusive formation of dimers over extended aggregates is demonstrated by atomic force microscopy (AFM) and diffusion ordered spectroscopy (DOSY) measurements as well as by theoretical calculations. Thus,The self-assembly of a bowl-shaped naphthalimide-annulated corannulene of high solubility has been studied in a variety of solvents by NMR and UV/Vis spectroscopy. Evaluation by the anti-cooperative K\(_2\)-K model revealed the formation of supramolecular dimers of outstanding thermodynamic stability. Further structural proof for the almost exclusive formation of dimers over extended aggregates is demonstrated by atomic force microscopy (AFM) and diffusion ordered spectroscopy (DOSY) measurements as well as by theoretical calculations. Thus, herein we present the first report of a supramolecular dimer of an annulated corannulene derivative in solution and discuss its extraordinarily high thermodynamic stability with association constants up to > 10\(^6\)M\(^-\) \(^1\) in methylcyclohexane, which is comparable to the association constants given for planar phthalocyanine and perylene bisimide dyes.show moreshow less

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Metadaten
Author: Rebecca Renner, Matthias Stolte, Frank Würthner
URN:urn:nbn:de:bvb:20-opus-204396
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):ChemistryOpen
Year of Completion:2020
Volume:9
Issue:1
Pagenumber:32-39
Source:ChemistryOpen (2019) 9:1, 32-39. https://doi.org/10.1002/open.201900291
DOI:https://doi.org/10.1002/open.201900291
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie
Tag:aelf-assembly; aggregation; corannulene; supramolecular chemistry; π-π-interactions
Release Date:2020/05/19
Collections:Open-Access-Publikationsfonds / Förderzeitraum 2019
Licence (German):License LogoCC BY-NC-ND: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell, Keine Bearbeitungen 4.0 International