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Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Neuhaus Frederik, Zobi Fabio, Brezesinski Gerald, Molin Marta Dal, Matile Stefan, Zumbuehl Andreas,
Project Exploring Stable Phospholipid Membranes
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Original article (peer-reviewed)

Journal Beilstein Journal of Organic Chemistry
Volume (Issue) 13
Page(s) 1099 - 1105
Title of proceedings Beilstein Journal of Organic Chemistry
DOI 10.3762/bjoc.13.109


© 2017 Neuhaus et al. It is currently not possible to directly measure the lateral pressure of a biomembrane. Mechanoresponsive fluorescent probes are an elegant solution to this problem but it requires first the establishment of a direct correlation between the membrane surface pressure and the induced color change of the probe. Here, we analyze planarizable dithienothiophene push–pull probes in a monolayer at the air/water interface using fluorescence microscopy, grazing-incidence angle X-ray diffraction, and infrared reflection–absorption spectroscopy. An increase of the lateral membrane pressure leads to a well-packed layer of the ‘flipper’ mechanophores and a clear change in hue above 18 mN/m. The fluorescent probes had no influence on the measured isotherm of the natural phospholipid DPPC suggesting that the flippers probe the lateral membrane pressure without physically changing it. This makes the flipper probes a truly useful addition to the membrane probe toolbox.