Lower‐rim‐modified Calix[4]arene‐Pyrrolotetrathiafulvalene molecular tweezers

Schlüter, Dirk; Korsching, Kai R.; Azov, Vladimir A.

doi:10.1002/ejoc.202100676

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Lower‐rim‐modified Calix[4]arene‐Pyrrolotetrathiafulvalene molecular tweezers

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Korsching, Kai R.
Department of Molecular Sensory Systems, Center of Advanced European Studies and Research (caesar), Max Planck Society;

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https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100676
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Citation

Schlüter, D., Korsching, K. R., & Azov, V. A. (2021). Lower‐rim‐modified Calix[4]arene‐Pyrrolotetrathiafulvalene molecular tweezers. European Journal of Organic Chemistry, 2021(31), 4469-4476. doi:10.1002/ejoc.202100676.

Cite as: https://hdl.handle.net/21.11116/0000-0009-2981-7

Abstract

An approach for the lower rim modification of the calix[4]arene-based molecular tweezes with monopyrrolo-tetrathiafulvalene(MPTTF) arms attached to the upper rim of calixarenes is described. First, calixarene-MPTTF conjugates with free hydroxylon the lower rim are synthesized using the Ullmann reaction, then hydroxyl groups are substituted by propargyl groups, which can be used for further modification by the click reaction. The new calixarene-TTF derivatives displayed reversible redox processes, as well as demonstrated binding affinity for electron-deficient molecular guests such as tetracyanoquinodimethane. The described synthetic approach will be used for the modular synthesis of molecular receptors tailored for specific applications.