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White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting

Bent N,N′‐diphenyl‐dihydrodibenzo[a,c]phenazine amphiphiles are introduced as mechanosensitive membrane probes that operate by an unprecedented mechanism, namely, unbending in the excited state as opposed to the previously reported untwisting in the ground and twisting in the excited state. Their du...

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Autores principales: Humeniuk, Heorhii V., Rosspeintner, Arnulf, Licari, Giuseppe, Kilin, Vasyl, Bonacina, Luigi, Vauthey, Eric, Sakai, Naomi, Matile, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099517/
https://www.ncbi.nlm.nih.gov/pubmed/29924457
http://dx.doi.org/10.1002/anie.201804662
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author Humeniuk, Heorhii V.
Rosspeintner, Arnulf
Licari, Giuseppe
Kilin, Vasyl
Bonacina, Luigi
Vauthey, Eric
Sakai, Naomi
Matile, Stefan
author_facet Humeniuk, Heorhii V.
Rosspeintner, Arnulf
Licari, Giuseppe
Kilin, Vasyl
Bonacina, Luigi
Vauthey, Eric
Sakai, Naomi
Matile, Stefan
author_sort Humeniuk, Heorhii V.
collection PubMed
description Bent N,N′‐diphenyl‐dihydrodibenzo[a,c]phenazine amphiphiles are introduced as mechanosensitive membrane probes that operate by an unprecedented mechanism, namely, unbending in the excited state as opposed to the previously reported untwisting in the ground and twisting in the excited state. Their dual emission from bent or “closed” and planarized or “open” excited states is shown to discriminate between micelles in water and monomers in solid‐ordered (S(o)), liquid‐disordered (L(d)) and bulk membranes. The dual‐emission spectra cover enough of the visible range to produce vesicles that emit white light with ratiometrically encoded information. Strategies to improve the bent mechanophores with expanded π systems and auxochromes are reported, and compatibility with imaging of membrane domains in giant unilamellar vesicles by two‐photon excitation fluorescence (TPEF) microscopy is demonstrated.
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spelling pubmed-60995172018-08-24 White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting Humeniuk, Heorhii V. Rosspeintner, Arnulf Licari, Giuseppe Kilin, Vasyl Bonacina, Luigi Vauthey, Eric Sakai, Naomi Matile, Stefan Angew Chem Int Ed Engl Communications Bent N,N′‐diphenyl‐dihydrodibenzo[a,c]phenazine amphiphiles are introduced as mechanosensitive membrane probes that operate by an unprecedented mechanism, namely, unbending in the excited state as opposed to the previously reported untwisting in the ground and twisting in the excited state. Their dual emission from bent or “closed” and planarized or “open” excited states is shown to discriminate between micelles in water and monomers in solid‐ordered (S(o)), liquid‐disordered (L(d)) and bulk membranes. The dual‐emission spectra cover enough of the visible range to produce vesicles that emit white light with ratiometrically encoded information. Strategies to improve the bent mechanophores with expanded π systems and auxochromes are reported, and compatibility with imaging of membrane domains in giant unilamellar vesicles by two‐photon excitation fluorescence (TPEF) microscopy is demonstrated. John Wiley and Sons Inc. 2018-06-20 2018-08-13 /pmc/articles/PMC6099517/ /pubmed/29924457 http://dx.doi.org/10.1002/anie.201804662 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Humeniuk, Heorhii V.
Rosspeintner, Arnulf
Licari, Giuseppe
Kilin, Vasyl
Bonacina, Luigi
Vauthey, Eric
Sakai, Naomi
Matile, Stefan
White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
title White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
title_full White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
title_fullStr White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
title_full_unstemmed White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
title_short White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
title_sort white‐fluorescent dual‐emission mechanosensitive membrane probes that function by bending rather than twisting
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099517/
https://www.ncbi.nlm.nih.gov/pubmed/29924457
http://dx.doi.org/10.1002/anie.201804662
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