Stereochemistry‐Controlled Supramolecular Architectures of New Tetrahydroxy‐Functionalised Amphiphilic Carbocyanine Dyes
Abstract: 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.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Stereochemistry‐Controlled Supramolecular Architectures of New Tetrahydroxy‐Functionalised Amphiphilic Carbocyanine Dyes ; volume:26 ; number:30 ; year:2020 ; pages:6919-6934 ; extent:16
Chemistry - a European journal ; 26, Heft 30 (2020), 6919-6934 (gesamt 16)
- Creator
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Schade, Boris
Singh, Abhishek Kumar
Wycisk, Virginia
Cuellar‐Camacho, Jose Luis
von Berlepsch, Hans
Haag, Rainer
Böttcher, Christoph
- DOI
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10.1002/chem.201905745
- URN
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urn:nbn:de:101:1-2022060308342002437106
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:31 AM CEST
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Associated
- Schade, Boris
- Singh, Abhishek Kumar
- Wycisk, Virginia
- Cuellar‐Camacho, Jose Luis
- von Berlepsch, Hans
- Haag, Rainer
- Böttcher, Christoph
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