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Stereochemistry‐Controlled Supramolecular Architectures of New Tetrahydroxy‐Functionalised Amphiphilic Carbocyanine Dyes
Author(s) -
Schade Boris,
Singh Abhishek Kumar,
Wycisk Virginia,
CuellarCamacho Jose Luis,
Berlepsch Hans,
Haag Rainer,
Böttcher Christoph
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905745
Subject(s) - conformational isomerism , cyanine , supramolecular chemistry , enantiomer , steric effects , amphiphile , chemistry , hydrogen bond , chirality (physics) , stereochemistry , crystallography , molecule , copolymer , organic chemistry , fluorescence , crystal structure , physics , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , quark , polymer
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.