Confined Spaces in [n]Cyclo-2,7-pyrenylenes
- A set of strained aromatic macrocycles based on [n]cyclo2,7-(4,5,9,10-tetrahydro)pyrenylenes is presented with size dependent photophysical properties. The K-region of pyrene was functionalized with ethylene glycol groups to decorate the outer rim and thereby confine the space inside the macrocycle. This confined space is especially pronounced for n = 5, which leads to an internal binding of up to 8.0×104 M–1 between the ether-decorated [5]cyclo-2,7-pyrenylene and shape complementary crown ether–cation complexes. Both, the ether-decorated [n]cyclo-pyrenylenes as well as one of their host–guest complexes have been structurally characterized by single crystal X-ray analysis. In combination with computational methods the structural and thermodynamic reasons for the exceptionally strong binding have been elucidated. The presented rim confinement strategy makes cycloparaphenylenes an attractive supramolecular host family with a favorable, size-independent read-out signature and bindingA set of strained aromatic macrocycles based on [n]cyclo2,7-(4,5,9,10-tetrahydro)pyrenylenes is presented with size dependent photophysical properties. The K-region of pyrene was functionalized with ethylene glycol groups to decorate the outer rim and thereby confine the space inside the macrocycle. This confined space is especially pronounced for n = 5, which leads to an internal binding of up to 8.0×104 M–1 between the ether-decorated [5]cyclo-2,7-pyrenylene and shape complementary crown ether–cation complexes. Both, the ether-decorated [n]cyclo-pyrenylenes as well as one of their host–guest complexes have been structurally characterized by single crystal X-ray analysis. In combination with computational methods the structural and thermodynamic reasons for the exceptionally strong binding have been elucidated. The presented rim confinement strategy makes cycloparaphenylenes an attractive supramolecular host family with a favorable, size-independent read-out signature and binding capabilities extending beyond fullerene guests.…
Autor*innen: | N. Grabicki, K. T. G. Nguyen, Steffen WeidnerORCiD, O. Dumele |
---|---|
Dokumenttyp: | Zeitschriftenartikel |
Veröffentlichungsform: | Verlagsliteratur |
Sprache: | Englisch |
Titel des übergeordneten Werkes (Englisch): | Angewandte Chemie-International Edition |
Jahr der Erstveröffentlichung: | 2021 |
Organisationseinheit der BAM: | 6 Materialchemie |
6 Materialchemie / 6.3 Strukturanalytik | |
Verlag: | Wiley VCH |
Jahrgang/Band: | 60 |
Ausgabe/Heft: | 27 |
Erste Seite: | 1 |
Letzte Seite: | 7 |
DDC-Klassifikation: | Naturwissenschaften und Mathematik / Chemie / Analytische Chemie |
Technik, Medizin, angewandte Wissenschaften / Ingenieurwissenschaften / Ingenieurwissenschaften und zugeordnete Tätigkeiten | |
Freie Schlagwörter: | Cycloparaphenylenes; Host–guest systems; Macrocycles; Molecular recognition; Supramolecular chemistry |
Themenfelder/Aktivitätsfelder der BAM: | Chemie und Prozesstechnik |
Chemie und Prozesstechnik / Chemische Charakterisierung und Spurenanalytik | |
Material | |
DOI: | 10.1002/anie.202102809 |
ISSN: | 1433-7851 |
Verfügbarkeit des Dokuments: | Datei im Netzwerk der BAM verfügbar ("Closed Access") |
Datum der Freischaltung: | 28.04.2021 |
Referierte Publikation: | Ja |
Datum der Eintragung als referierte Publikation: | 03.06.2021 |