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    Chirality-Controlled Self-Assembly of Amphiphilic Dibenzo[6]helicenes into Langmuir-Blodgett Thin Films

    Year: 2019

    Journal: Chem.-Eur. J., Volume 25, 1-Sep, page 11494–11502

    Authors: Holec, Jan; Rybacek, Jiri; Vacek, Jaroslav; Karras, Manfred; Bednarova, Lucie; Budesinsky, Milos; Slusna, Michaela; Holy, Petr; Schmidt, Bernd; Stara, Irena G.; Stary, Ivo

    Organizations: Czech Science FoundationGrant Agency of the Czech Republic [16-08294S]; Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences [RVO: 61388963]; German Academic Exchange Service (DAAD)Deutscher Akademischer Austausch Dienst (DAAD) [57314603]; Ministry of Education, Youth and Sports of the Czech RepublicMinistry of Education, Youth & Sports - Czech Republic [LM2015073]

    Keywords: arenes; chirality; helical structures; Langmuir-Blodgett films; self-assembly

    Racemic and highly enantioenriched 3-methoxycarbonyl, 3-carboxy, and 3-hydroxymethyl derivatives of dibenzo[6]helicene were prepared. The Langmuir layers of these helicenes were formed at the air-water interface and transferred onto solid substrates to afford Langmuir-Blodgett films, which were then studied by ambient atomic force microscopy and (chir)optical spectroscopy. Significant differences were found in the behaviour of the Langmuir layers as well as in the morphology, UV/Vis, electronic circular dichroism (ECD), and fluorescence spectra of the Langmuir-Blodgett thin films depending on the molecular chirality and nature of the polar group. The experimental results were supported by molecular dynamics simulations.
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