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Synthesis of All‐Benzene Multi‐Macrocyclic Nanocarbons by Post‐Functionalization of <i>meta</i>‐Cycloparaphenylenes

Jia‐Nan Gao, An Bu, Yi‐Ming Chen, Mianling Huang, Zhi Chen, Xiaopeng Li, Chen‐Ho Tung, Li‐Zhu Wu, Huan Cong

2024Angewandte Chemie International Edition20 citationsDOIOpen Access PDF

Abstract

Expanding the diversity of multi-macrocyclic nanocarbons, particularly those with all-benzene scaffolds, represents intriguing yet challenging synthetic tasks. Complementary to the existing synthetic approaches, here we report an efficient and modular post-functionalization strategy that employs iridium-catalyzed C-H borylation of the highly strained meta-cycloparaphenylenes (mCPPs) and an mCPP-derived catenane. Based on the functionalized macrocyclic synthons, a number of novel all-benzene topological structures including linear and cyclic chains, polycatenane, and pretzelane have been successfully prepared and characterized, thereby showcasing the synthetic utility and potential of the post-functionalization strategy.

Topics & Concepts

Surface modificationSynthonBorylationCombinatorial chemistryBenzeneIridiumChemistryNanotechnologyMaterials scienceCatalysisOrganic chemistryArylAlkylPhysical chemistryOrganoboron and organosilicon chemistryCovalent Organic Framework ApplicationsBoron Compounds in Chemistry
Synthesis of All‐Benzene Multi‐Macrocyclic Nanocarbons by Post‐Functionalization of <i>meta</i>‐Cycloparaphenylenes | Litcius