[3]Rotaxanes with Mixed Axles: Polyynes and Cumulenes

Beitrag in einer Fachzeitschrift

Details zur Publikation

Autorinnen und Autoren: Franz M, Januszewski J, Hampel F, Tykwinski RR
Zeitschrift: European Journal of Organic Chemistry
Jahr der Veröffentlichung: 2019
Band: 2019
Heftnummer: 21
Seitenbereich: 3503-3512
ISSN: 1434-193X
eISSN: 1099-0690


Tailoring synthetic strategies toward complex, but well-defined, molecular architectures is an important aspect of Today's organic chemistry. Herein, we present designs to build up [3]rotaxanes of Type 2.1 and Type 3 that feature both a polyyne and a cumulene axle in a single mechanically interlocked molecule. The combination of two sp-hybridized carbon chains was achieved by functionalization of a phenanthroline-based macrocycle, which allowed the coupling of two [2]rotaxanes toward Type 3 [3]rotaxanes with two polyynes, two cumulenes, or one polyyne and one cumulene axle. The structures have been established by NMR and UV/Vis spectroscopies, as well as high-resolution mass spectrometry. A [3]rotaxane of Type 3, featuring two [9]cumulene axles, has been assembled and spectroscopically characterized despite expectations that it would be unstable. This represents only the second cumulene rotaxane reported to date. All designs and attempts to form [3]rotaxanes of Type 2.1, which combine a polyyne and cumulene threaded through a single macrocycle, have been unsuccessful.

FAU-Autorinnen und Autoren / FAU-Herausgeberinnen und Herausgeber

Franz, Michael
Lehrstuhl für Organische Chemie I
Hampel, Frank Dr.
Lehrstuhl für Organische Chemie I
Januszewski, Johanna Dr.
Lehrstuhl für Organische Chemie I

Einrichtungen weiterer Autorinnen und Autoren

University of Alberta


Franz, M., Januszewski, J., Hampel, F., & Tykwinski, R.R. (2019). [3]Rotaxanes with Mixed Axles: Polyynes and Cumulenes. European Journal of Organic Chemistry, 2019(21), 3503-3512. https://dx.doi.org/10.1002/ejoc.201900188

Franz, Michael, et al. "[3]Rotaxanes with Mixed Axles: Polyynes and Cumulenes." European Journal of Organic Chemistry 2019.21 (2019): 3503-3512.


Zuletzt aktualisiert 2019-25-06 um 08:47