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

Neuhaus, Frederik; Zobi, Fabio; Brezesinski, Gerald; Dal Molin, Marta; Matile, Stefan; Zumbuehl, Andreas

doi:10.3762/bjoc.13.109

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

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Brezesinski, Gerald
Gerald Brezesinski, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Neuhaus, F., Zobi, F., Brezesinski, G., Dal Molin, M., Matile, S., & Zumbuehl, A. (2017). Correlation of surface pressure and hue of planarizable push–pull chromophores at the air/water interface. Beilstein Journal of Organic Chemistry, 13, 1099-1105. doi:10.3762/bjoc.13.109.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002D-73A9-1

Abstract

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.