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Article Dans Une Revue Chemistry - An Asian Journal Année : 2021

Switch‐On Diketopyrrolopyrrole‐Based Chemosensors for Cations Possessing Lewis Acid Character

G. Dinesh Kumar
  • Fonction : Auteur
Denis Jacquemin
Daniel Gryko

Résumé

For the first time diketopyrrolopyrroles (DPPs) have been synthesized directly from nitriles possessing (aza)crown ethers leading to macrocycle-dye hybrids. Depending on the nature of the linkage between DPP and macrocyclic ring, various coordination effects are found. The strong interaction of the cations possessing Lewis acid character such as Li+ , Mg2+ and Zn2+ with 2-aminopyridin-4-yl-DPPs, leading to a bathochromic shift of both emission and absorption, as well as to strong enhancement of fluorescence was rationalized in terms of strong binding of these cations to the N=C-NR2 functionality. The same effect has been observed for protonation. Depending on the size and the structure of the macrocyclic ring the complexation of cations by aza-crown ethers plays an important but secondary role. The interaction of Na+ and K+ with 2-aminopyridin-4-yl-DPPs leads to moderate enhancement of fluorescence due to the aza-crown ethers binding. The very weak fluorescence of DPP bearing 2-dialkylamino-pyridine-4-yl substituents is due to the closely lying T2 state and the resulting intersystem crossing.

Domaines

Chimie
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Dates et versions

hal-03376421 , version 1 (13-10-2021)

Identifiants

Citer

G. Dinesh Kumar, Marzena Banasiewicz, Denis Jacquemin, Daniel Gryko. Switch‐On Diketopyrrolopyrrole‐Based Chemosensors for Cations Possessing Lewis Acid Character. Chemistry - An Asian Journal, 2021, 16 (4), pp.355-362. ⟨10.1002/asia.202001376⟩. ⟨hal-03376421⟩
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