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    Assembly of T-Shaped Amphiphilic Thiazoles on the Air-Water Interface: Impact of Polar Chromophore Moieties, as Well as Dipolarity and pi-Extension of the Chromophore on the Supramolecular Structure

    Year: 2019

    Journal: Langmuir, Volume 35, 1-Feb, page 2587–2600

    Authors: Hupfer, Maximilian L.; Kaufmann, Martin; Preiss, Julia; Weiss, Dieter; Beckert, Rainer; Dietzek, Benjamin; Presselt, Martin

    Organizations: German Research Foundation (DFG)German Research Foundation (DFG) [PR 1415/2]; Bundesministerium fur Bildung and Forschung (BMBF)Federal Ministry of Education & Research (BMBF) [FKZ 03EK3507]; Nagelschneider Stiftung

    The supramolecular structure essentially determines the properties of organic thin films. In this work, we systematically investigate the influence of the chromophore on the supramolecular structure formation at air-water interfaces by means of the Langmuir-Blodgett technique. Therefore, we focus on the recently introduced class of double-anchor T-shaped amphiphilic dyes, namely, 4-hydroxy-thiazole chromophores that are centrally equipped with an amphiphilicity-inducing hexanoic acid. The thiazoles contain hydrophilic subphase-anchor groups in the 2-position (4-N,N-dimethylaminophenyl (Am), 2-pyridyl (Py), and 4-nitrophenyl (Ni)), whereas the chromophores are systematically extended in the 5-position with various substituents. The combination of the Langmuir technique with online fluorescence measurements revealed that the pi-pi interactions that are pronounced in the case of 4-methoxybiphenyl derivatives yield the most distinct supramolecular structures. Whereas in the case of Py and Ni derivatives ordered J-type supramolecular structures in microdomains are formed, the Am derivative forms ordered supramolecular structures that are more homogeneous, which are, however, not stabilized by J-type dipolar interactions. Because of the synergetic pi-pi and dipolar stabilizations, the Ni derivative bearing the 4-methoxybiphenyl unit forms exceptionally stable quasi two-dimensional Langmuir monolayers reaching very high surface pressures beyond 60 mN/m without any sign of disturbance of the Langmuir monolayer.
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