Stereochemistry-Controlled Supramolecular Architectures of New Tetrahydroxy-Functionalised Amphiphilic Carbocyanine Dyes.

Autor: Schade B; Forschungszentrum für Elektronenmikroskopie und Gerätezentrum BioSupraMol, Institut für Chemie und Biochemie, Freie Universität Berlin, Fabeckstraße 36a, 14195, Berlin, Germany., Singh AK; Institut für Chemie und Biochemie, Organische Chemie, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany., Wycisk V; Institut für Chemie und Biochemie, Organische Chemie, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany., Cuellar-Camacho JL; Institut für Chemie und Biochemie, Organische Chemie, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany., von Berlepsch H; Forschungszentrum für Elektronenmikroskopie und Gerätezentrum BioSupraMol, Institut für Chemie und Biochemie, Freie Universität Berlin, Fabeckstraße 36a, 14195, Berlin, Germany., Haag R; Institut für Chemie und Biochemie, Organische Chemie, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany., Böttcher C; Forschungszentrum für Elektronenmikroskopie und Gerätezentrum BioSupraMol, Institut für Chemie und Biochemie, Freie Universität Berlin, Fabeckstraße 36a, 14195, Berlin, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 May 26; Vol. 26 (30), pp. 6919-6934. Date of Electronic Publication: 2020 Apr 30.
DOI: 10.1002/chem.201905745
Abstrakt: The syntheses of novel amphiphilic 5,5',6,6'-tetrachlorobenzimidacarbocyanine (TBC) dye derivatives with aminopropanediol head groups, which only differ in stereochemistry (chiral enantiomers, meso form and conformer), are reported. For the achiral meso form, a new synthetic route towards asymmetric cyanine dyes was established. All compounds form J aggregates in water, the optical properties of which were characterised by means of spectroscopic methods. The supramolecular structure of the aggregates is investigated by means of cryo-transmission electron microscopy, cryo-electron tomography and AFM, revealing extended sheet-like aggregates for chiral enantiomers and nanotubes for the mesomer, respectively, whereas the conformer forms predominately needle-like crystals. The experiments demonstrate that the aggregation behaviour of compounds can be controlled solely by head group stereochemistry, which in the case of enantiomers enables the formation of extended hydrogen-bond chains by the hydroxyl functionalities. In case of the achiral meso form, however, such chains turned out to be sterically excluded.
(© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
Databáze: MEDLINE
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