Journal
CHEMPHYSCHEM
Volume 10, Issue 18, Pages 3260-3264Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cphc.200900649
Keywords
density functional calculations; hydrogen bonding; isatin; liquid crystals; supramolecular chemistry
Funding
- CPU time by the Regional Computing Centre RRZK, Koln (Germany)
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Spatially organized chromophores can be beneficial for advanced applications like for example, organic solar cells, laser technology or non-linear optic devices as well as supramolecular photochemistry. Of particular interest are non-static ordered forms of molecular organization as for example, liquid crystals. With this in mind we synthesised four new regioisomeric isatin derivatives by Suzuki-Miyaura coupling of 4-dodecyloxyphenylboronic acid with all four possible regioisomers of bromoisatin. Liquid crystalline properties are found for 5-(4-dodecyloxyphenyl)isatin, while the other regioisomers do not display a mesomorphic behaviour. The synthesis, physicochemical investigations including polarization microscopy, differential scanning calorimetry and X-ray investigations are discussed and accompanied with density functional theory calculations with respect to the target molecules and their possible H-bonded aggregates. Two distinct setups of supramolecular assemblies for such isatin derivatives are discussed and a model for the mesophase is proposed.
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