Self-Assembly of bowl-shaped naphthalimide-annulated corannulene
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- 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.…
Autor(en): | Rebecca Renner, Matthias Stolte, Frank WürthnerORCiDGND |
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URN: | urn:nbn:de:bvb:20-opus-204396 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | ChemistryOpen |
Erscheinungsjahr: | 2020 |
Band / Jahrgang: | 9 |
Heft / Ausgabe: | 1 |
Seitenangabe: | 32-39 |
Originalveröffentlichung / Quelle: | ChemistryOpen (2019) 9:1, 32-39. https://doi.org/10.1002/open.201900291 |
DOI: | https://doi.org/10.1002/open.201900291 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie |
Freie Schlagwort(e): | aelf-assembly; aggregation; corannulene; supramolecular chemistry; π-π-interactions |
Datum der Freischaltung: | 19.05.2020 |
Sammlungen: | Open-Access-Publikationsfonds / Förderzeitraum 2019 |
Lizenz (Deutsch): | CC BY-NC-ND: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell, Keine Bearbeitungen 4.0 International |