Mixed N-Aryl/Alkyl Substitution Favours an Unusual Tautomer of Near-Infrared Absorbing Azacalixphyrins - Archive ouverte HAL Access content directly
Journal Articles New Journal of Chemistry Year : 2020

Mixed N-Aryl/Alkyl Substitution Favours an Unusual Tautomer of Near-Infrared Absorbing Azacalixphyrins

Lucien Lavaud
  • Function : Author
Cloé Azarias
  • Function : Author
Gabriel Canard
Denis Jacquemin
Olivier Siri

Abstract

Azacalixphyrins are bis-zwitterionic aromatic macrocycles that feature absorption properties in the near-infrared range. Their N-substitution is an efficient strategy for tuning the absorption maxima by stabilizing different tautomeric forms depending on the nature of the substituent (alkyl or aryl give 1-5 or 2-6 tautomers, respectively). This work depicts the synthesis of a new azacalixphyrin presenting both aryl and alkyl substituents. The joint experimental and theoretical study supports that the substitution pattern can be manipulated to counterbalance the repulsion of the two peripheral cationic charges to favour an unusual 5-7 tautomer.
Fichier principal
Vignette du fichier
HAL_ACP Mixed Alkyl-Aryl.pdf (1.32 Mo) Télécharger le fichier
Origin Files produced by the author(s)
Loading...

Dates and versions

hal-02962328 , version 1 (15-10-2020)

Identifiers

Cite

Lucien Lavaud, Cloé Azarias, Gabriel Canard, Simon Pascal, Denis Jacquemin, et al.. Mixed N-Aryl/Alkyl Substitution Favours an Unusual Tautomer of Near-Infrared Absorbing Azacalixphyrins. New Journal of Chemistry, 2020, ⟨10.1039/D0NJ04587J⟩. ⟨hal-02962328⟩
37 View
83 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More