Author: Duncan W. Bruce

Extending the halogen-bonded supramolecular synthon concept to 1,3,4-oxadiazole derivatives

A series of five crystal structures of 1:1 halogen-bonded complexes were obtained from 4-[5-(4-alkoxyphenyl)-1,3,4-oxadiazole-2-yl]pyridine and 1,3,5-trifluorotriiodobenzene. Electronic structure calculations show that the N(oxadiazole)⋯I interaction in the new synthon is as strong as the classic N(pyridine)⋯I interaction. Oxygen to sulfur atom subsitution on the oxadiazole ring results in a different supramolecular packing where the N(pyridine)⋯I interaction is favored, which could be rationalized by the changes in the molecular electrostatic potential predicted from the theoretical calculations.

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Superfluorinated ionic liquid crystals based on supramolecular, halogen-bonded anions

Unconventional ionic liquid crystals in which the liquid crystallinity is enabled by halogen-bonded supramolecular anions [CnF2 n+1-I⋯I⋯I-CnF2 n+1]- are reported. The material system is unique in many ways, demonstrating for the first time 1) ionic, halogen-bonded liquid crystals, and 2) imidazolium-based ionic liquid crystals in which the occurrence of liquid crystallinity is not driven by the alkyl chains of the cation. Out of the ordinary: The high directionality of halogen bonds and the fluorophobic effect were exploited in the design and synthesis of a new family of unconventional superfluorinated ionic liquid crystals. The liquid crystallinity of the system is driven by halogen-bonded…

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Synthesis and mesomorphism of related series of triphilic ionic liquid crystals based on 1,2,4-triazolium cations

Abstract The synthesis, liquid crystal and conductivity properties of a series of 27 salts based on the 5-(4-(alkyloxy)phenyl)-1,2,4-triazol-4-ium cation bearing a perfluoroalkyl chain with triflate, tetrafluoroborate and bistriflimide anion are reported. The cations are regarded as triphilic on account of their three distinct regions – hydrocarbon, fluorocarbon and ionic. The mesophases were characterised by a combination of polarised optical microscopy, calorimetry and small-angle scattering experiments using both X-rays and neutrons, while thermal stability was probed using thermogravimetric analysis. The liquid crystal properties are found to be dependent on the anion and the length of …

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1,2,4-Triazolium ions as flexible scaffolds for the construction of polyphilic ionic liquid crystals

A novel scaffold for the construction of self-organised ionic liquids and ionic liquid crystals bearing both perfluorocarbon and hydrocarbon moieties has been developed. The phase behaviour and physical properties of these materials can be tuned as a function of chain length and fluorine content and significant structural elaboration is possible, giving a highly flexible system.

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