Aromatic Ring‐Fused Amidine Based Allosteric Receptors Activated by Guest‐Induced π‐Conjugation Switching

Abstract: Amidine‐substituted allosteric receptors 2 a and 2 b for benzenediols were synthesized. Receptor 2 a with five‐membered amidines exhibited greater allostericity than the amide‐substituted receptor 1, while 2 b with six‐membered amidines exhibited less allostericity. NMR titration experiments revealed that a significant enthalpic factor was involved in the allostericity of these receptors. X‐ray and DFT optimized structures of 2 a and 2 b revealed that 2 a adopted a coplanar conformation with π‐conjugation between the amidines and the phenylene ring of the hydrindacene framework, resulting in high allostericity due to inactivation of the initial binding.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
Aromatic Ring‐Fused Amidine Based Allosteric Receptors Activated by Guest‐Induced π‐Conjugation Switching ; day:17 ; month:11 ; year:2024 ; extent:10
ChemPlusChem ; (17.11.2024) (gesamt 10)

Urheber
Kataoka, Takayuki
Matsumura, Kotaro
Ono, Kosuke
Tsuchido, Yoshitaka
Kawai, Hidetoshi

DOI
10.1002/cplu.202400612
URN
urn:nbn:de:101:1-2411181317441.581824816550
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
15.08.2025, 07:27 MESZ

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Beteiligte

  • Kataoka, Takayuki
  • Matsumura, Kotaro
  • Ono, Kosuke
  • Tsuchido, Yoshitaka
  • Kawai, Hidetoshi

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