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Updated: Jul 30, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Leveraging Torsional and Steric Strains: A Pre-macrocyclization Strategy Enables Conformation-Specific Fullerene
Pawan Kumar1, V B Raja Mani Kandan1, Prabukumar Balakrishnan1
1Department of Chemistry, Indian Institute of Technology Madras, 600036, Chennai, Tamil Nadu, India.
Abstract:
Though the chemistry of resorcinarenes is half a century old, the conformationally-locked resorcinarene crowns are generally constructed using hydrogen bonds or covalent tethers. Often, covalent tethering involves extra post-macrocyclization steps involving upper-rim functionalities. We have leveraged the torsional and steric strains through α-substituents of the lower-rim C-alkyl chains and accomplished conformationally-rigid fluorescent m-cyclophane deep-crowns in a predetermined way. The strategy offers a pre-macrocyclization route conserving upper-rim functionalities, an aspect overlooked in resorcinarene chemistry. X-ray structural and computational analyses unveil the cause for conformational rigidity in m-cyclophanes due to α-branching in C-alkyls (linear vs. α-/β-branched). The conformationally-locked fluorescent deep-crown with a preorganized cavity captures hydrophobic spherical guest C60 in both solution and solid states specifically, when compared to conformationally-dynamic boats, enabling conformation-specific binding.
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