Mixed N -aryl/alkyl substitution favours an unusual tautomer of near-infrared absorbing azacalixphyrins

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...

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Bibliographic Details
Published in:New journal of chemistry 2020-11, Vol.44 (42), p.18130-18137
Main Authors: Lavaud, Lucien, Azarias, Cloé, Canard, Gabriel, Pascal, Simon, Jacquemin, Denis, Siri, Olivier
Format: Article
Language:English
Subjects:
Absorption spectra
Aromatic compounds
Chemical Sciences
Near infrared radiation
NMR
Nuclear magnetic resonance
or physical chemistry
Organic chemistry
Substitutes
Tautomers
Theoretical and
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Summary: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.
ISSN:1144-0546
1369-9261
DOI:10.1039/D0NJ04587J