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Updated: Apr 21, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Ag2CO3-Mediated Oxidative Access to Calix[4]Diphenoquinones: Synthesis, Conformational Features, and Cavity
Ti Wu1, Yuguang Feng1, Wenguang Wang1
1Laboratory of Optoelectronic and Information Marking Materials, Beijing Institute of Graphic Communication, Beijing, P. R. China.
Abstract:
Calix[4]diphenoquinones represent a promising class of redox-active macrocycles with potential applications in supramolecular chemistry and functional organic materials, yet their systematic synthesis and structural characterization have remained limited. Here, we report a mild and efficient Ag2CO3-mediated oxidation strategy that enables the near-quantitative synthesis of DPQ1∼4. Electrochemical measurements reveal well-defined quinone redox behavior and LUMO levels around -4.0 eV, indicative of air-stable electron-transporting characteristics. NMR analyses demonstrate tunable conformations, with most intermediates adopting cone arrangements, whereas DPQ3 and DPQ4 preferentially form 1,3-alternate structures due to intramolecular hydrogen bonding or steric effects. Single-crystal analysis further shows that DPQ2 assembles into a chair-like 1,3-alternate macrocycle capable of encapsulating an ethanol molecule.
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