Affiliation:
1. Department of Chemistry & Biochemistry and Material Science Institute University of Oregon Eugene Oregon 97403 USA
2. Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM) Friedrich-Alexander-University Erlangen-Nuremberg Erlangen Bavaria 91058 Germany
3. Department of Chemistry College of Chemistry and Chemical Engineering State Key Laboratory of Physical Chemistry of Solid Surfaces Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry Xiamen University Xiamen 361005 China
Abstract
AbstractDeriving 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).
Funder
Deutsche Forschungsgemeinschaft
National Natural Science Foundation of China
Fundamental Research Funds for the Central Universities
Fonds der Chemischen Industrie
Hanns-Seidel-Stiftung
National Science Foundation
State Key Laboratory of Physical Chemistry of Solid Surfaces, Xiamen University
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
8 articles.
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