Tunable Macrocyclic Polyparaphenylene Nanolassos via Copper-Free Click Chemistry

Schaub TA, Zieleniewska A, Kaur R, Minameyer M, Yang W, Schüßlbauer C, Zhang L, Freiberger M, Zakharov LN, Drewello T, Dral PO, Guldi DM, Jasti R (2023)

Publication Type: Journal article

Publication year: 2023


DOI: 10.1002/chem.202300668


Deriving diverse compound libraries from a single substrate in high yields remains to be a challenge in cycloparaphenylene chemistry. In here, a strategy for the late-stage functionalization of shape-persistent alkyne-containing cycloparaphenylene has been explored using readily available azides. The copper-free [3+2]azide-alkyne cycloaddition provided high yields (>90 %) in a single reaction step. Systematic variation of the azides from electron-rich to -deficient shines light on how peripheral substitution influences the characteristics of the resulting adducts. We find that among the most affected properties are the molecular shape, the oxidation potential, excited-state features, and affinities towards different fullerenes. Joint experimental and theoretical results are presented including calculations with the state-of-the-art, artificial intelligence-enhanced quantum mechanical method 1 (AIQM1).

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Schaub, T.A., Zieleniewska, A., Kaur, R., Minameyer, M., Yang, W., Schüßlbauer, C.,... Jasti, R. (2023). Tunable Macrocyclic Polyparaphenylene Nanolassos via Copper-Free Click Chemistry. Chemistry - A European Journal. https://doi.org/10.1002/chem.202300668


Schaub, Tobias A., et al. "Tunable Macrocyclic Polyparaphenylene Nanolassos via Copper-Free Click Chemistry." Chemistry - A European Journal (2023).

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