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.

Metadaten
Verfasserangaben:	Jan Holec GND, Jiří Rybáček GND, Jaroslav Vacek GND, Manfred Karras ORCiD GND, Lucie Bednárová, Milos Budesinsky ORCiD, Michaela Slusna, Petr Holy, Bernd Schmidt ORCiD GND, Irena G. Stará ORCiD, Ivo Starý ORCiD
DOI:	https://doi.org/10.1002/chem.201901695
ISSN:	0947-6539
ISSN:	1521-3765
Pubmed ID:	https://pubmed.ncbi.nlm.nih.gov/31095794
Titel des übergeordneten Werks (Englisch):	Chemistry - a European journal
Verlag:	Wiley-VCH
Verlagsort:	Weinheim
Publikationstyp:	Wissenschaftlicher Artikel
Sprache:	Englisch
Datum der Erstveröffentlichung:	16.05.2019
Erscheinungsjahr:	2019
Datum der Freischaltung:	15.01.2021
Freies Schlagwort / Tag:	Langmuir-Blodgett films; arenes; chirality; helical structures; self-assembly
Band:	25
Ausgabe:	49
Seitenanzahl:	9
Erste Seite:	11494
Letzte Seite:	11502
Fördernde 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]
Organisationseinheiten:	Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie und Biologie
DDC-Klassifikation:	5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer Review:	Referiert