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Mechanosensitive membrane probes: push-pull papillons

Publié dansSupramolecular Chemistry, vol. 32, no. 2, p. 106-111
Date de publication2020
Résumé

Design, synthesis and evaluation of push-pull N,N′-diphenyl-dihydrodibenzo[a,c]phenazines are reported. Consistent with theoretical predictions, donors and acceptors attached to the bent mechanophore are shown to shift absorption maxima to either red or blue, depending on their positioning in the chromophore. Redshifted excitation of push-pull fluorophores is reflected in redshifted emission of both bent and planar excited states. The intensity ratios of the dual emission in more and less polar solvents imply that excited-state (ES) planarization decelerates with increasing fluorophore macrodipole, presumably due to attraction between the wings of closed papillons. ES planarization of highly polarisable papillons is not observed in lipid bilayer membranes. All push-pull papillon amphiphiles excel with aggregation-induced emission (AIE) from bent ES as micelles in water and mechanosensitivity in viscous solvents. They are not solvatochromic and only weakly fluorescent (QY < 4%).

Citation (format ISO)
HUMENIUK, Heorhii et al. Mechanosensitive membrane probes: push-pull papillons. In: Supramolecular Chemistry, 2020, vol. 32, n° 2, p. 106–111. doi: 10.1080/10610278.2019.1702193
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Identifiants
ISSN du journal1061-0278
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Informations techniques

Création02/03/2020 11:00:00
Première validation02/03/2020 11:00:00
Heure de mise à jour15/03/2023 21:12:02
Changement de statut15/03/2023 21:12:01
Dernière indexation17/01/2024 09:06:22
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