Journal article

Authors list: Volkmann, J; Kohrs, D; Bernt, F; Wegner, HA

Publication year: 2022

Pages: e202101357-

Journal: European Journal of Organic Chemistry

Volume number: 2022

Issue number: 4

ISSN: 1434-193X

eISSN: 1099-0690

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/ejoc.202101357

Publisher: Wiley

Abstract: 
Herein, we report the synthesis and investigation of a substituted [10]cycloparaphenylene (CPP) incorporating a diethylphthalane unit. An efficient strategy relying on a symmetric built-up starting with propargyl ether as [2 + 2 + 2] cycloaddition precursor was developed. The straightforward synthesis required overcoming unexpected obstacles within the [2 + 2 + 2] cycloaddition, protection and aromatization. These results give valuable insights for accessing CPPs with highly substituted subunits. Finally, a seven-step synthesis with an overall yield of 8% provided the target nanoring, including good to excellent yields for the critical macrocyclization and aromatization. The synthesized nanohoop exhibits a hypsochromic shift in fluorescence and absorption, compared to the unsubstituted [10]CPP. This observation is proposedly caused by an increased torsion angle between the bivalent substituted phenyl moieties and the adjacent units.

Harvard Citation style: Volkmann, J., Kohrs, D., Bernt, F. and Wegner, H. (2022) Synthesis of a Substituted [10]Cycloparaphenylene through [2+2+2] Cycloaddition, European Journal of Organic Chemistry, 2022(4), Article e202101357. p. e202101357. https://doi.org/10.1002/ejoc.202101357

APA Citation style: Volkmann, J., Kohrs, D., Bernt, F., & Wegner, H. (2022). Synthesis of a Substituted [10]Cycloparaphenylene through [2+2+2] Cycloaddition. European Journal of Organic Chemistry. 2022(4), Article e202101357, e202101357. https://doi.org/10.1002/ejoc.202101357