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

  • 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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Author details:Jan HolecGND, Jiří RybáčekGND, Jaroslav VacekGND, Manfred KarrasORCiDGND, Lucie Bednárová, Milos BudesinskyORCiD, Michaela Slusna, Petr Holy, Bernd SchmidtORCiDGND, Irena G. StaráORCiD, Ivo StarýORCiD
DOI:https://doi.org/10.1002/chem.201901695
ISSN:0947-6539
ISSN:1521-3765
Pubmed ID:https://pubmed.ncbi.nlm.nih.gov/31095794
Title of parent work (English):Chemistry - a European journal
Publisher:Wiley-VCH
Place of publishing:Weinheim
Publication type:Article
Language:English
Date of first publication:2019/05/16
Publication year:2019
Release date:2021/01/15
Tag:Langmuir-Blodgett films; arenes; chirality; helical structures; self-assembly
Volume:25
Issue:49
Number of pages:9
First page:11494
Last Page:11502
Funding institution: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]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie und Biologie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer review:Referiert
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