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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Calix[n]triazoles and Related Conformational Studies
Illan Kim1, Kyoung Chul Ko2, Woo Ram Lee3
1College of Pharmacy, Seoul National University , 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea.
New calix[n]triazole compounds were synthesized and their solid-state structures analyzed. Theoretical studies revealed the critical role of intermolecular interactions in crystal conformer determination for these calixarene derivatives.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Computational Chemistry
Background:
- Calixarenes are a well-established class of macrocyclic compounds with diverse applications.
- Exploring new derivatives expands the scope of calixarene chemistry and their potential uses.
- Calix[n]triazoles represent novel derivatives within the calixarene family.
Purpose of the Study:
- To synthesize novel calix[n]triazole compounds.
- To determine the solid-state structures and conformations of synthesized calix[n]triazoles.
- To investigate the influence of intermolecular interactions on crystal conformers using theoretical calculations.
Main Methods:
- Iterative convergent synthesis strategy.
- Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) for compound synthesis.
- X-ray crystallography for solid-state structure determination.
- Density Functional Theory (DFT) calculations for theoretical studies.
Main Results:
- Successful synthesis of calix[n]triazole compounds (2-4).
- Solid-state structures revealed 1,2-alternate and partial cone conformations for calix[4]triazole and calix[5]triazole, respectively.
- DFT calculations identified stable monomeric conformers: 1,3-alternate for calix[4]triazole, 1,3-alternate for calix[5]triazole, and 1,3,5-alternate for calix[6]triazole.
- Intermolecular interactions were found to be crucial in dictating crystal conformers.
Conclusions:
- Calix[n]triazoles are successfully developed as new calixarene derivatives.
- The study elucidates the conformational preferences in both solid-state and monomeric forms.
- Understanding conformational behavior is key for designing functional supramolecular systems based on calix[n]triazoles.
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