A new family of star shaped 1,2,4-oxadiazole derivatives with the variation in the number of flexible peripheral tails have been synthesized and characterized. It is interesting to note that the number of flexible tails at the periphery dictated the self-assembly and the photophysical behavior. The compound with three flexible tails stabilized the crystalline state with lamellar packing, and did not show organogelation, but showed blue emission in crystalline and thin film states. The compound with six flexible tails stabilized the hexagonal columnar liquid crystalline state and it showed the ability to gelate in nonpolar solvents at a concentration less than 1 weight percent, qualifying it as a supergelator, where π–π interactions play a major role. This phenomenon is very rare, in comparison to earlier reports where supergelation is supported by H-bonding interactions. Besides its capability to form a self-standing, moldable gel, this compound also exhibited aggregation-induced emission (AIE), which persisted even in the xerogel state. X-ray diffraction studies unraveled the rectangular columnar self-assembly in the gel state. The columnar order and emissive nature in the liquid crystal and xerogel states makes this molecule promising for application in emissive displays. Compounds with nine alkyl tails stabilized a long range columnar hexagonal phase. This report emphasizes the importance of various non-covalent interactions in deciding the nature of self-assembly.

Aromatic π–π driven supergelation, aggregation induced emission and columnar self-assembly of star-shaped 1,2,4-oxadiazole derivatives

Two series of highly π-conjugated calamitic liquid crystals containing a sulphur-based heterocyclic core, 1,3,4-thiadiazole or 1,3-thiazole ring, were synthesised and characterised. The part containing the heterocycle was linked to a π-extended mesogenic unit (phenyl, biphenyl, naphthyl and phenylbenzoate) through a carbon–carbon triple bond by Sonogashira’s cross coupling, in order to exhibit the liquid crystalline and luminescent properties. These compounds exhibited liquid crystalline behaviour in a special SmC phase presented by all compounds, characterised by polarised optical microscopy, differential scanning calorimetry and X-ray diffraction. Some compounds in the thiazole series showed much higher ordered phases below the SmC phase characterised as tilted hexatic phases. All the compounds showed blue luminescence in the solution and a study regarding temperature-dependent emission was performed in their pure state. The phase transitions upon heating were followed by a significant decrease in the e...

Luminescent liquid crystals containing a sulphur-based heterocyclic core

New photoactive D-π-A-π-D benzothiadiazole derivative: Synthesis, thermal and photophysical properties

Benzothiadiazole-based D-π-A-π-D fluorophores: Synthesis, self-assembly, thermal and photophysical characterization

Synthesis of Functionalized Organoselenium Materials: Selenides and Diselenides Containing Cholesterol

New fluorescent liquid crystalline (LC) compounds containing the 2,1,3-benzothiadiazole chromophore as the central core substituted with 1,2,4-oxadiazole, 1,2,3-triazole and 1,2-isoxazole heterocycles were synthesised and their mesophases characterised by polarised optical microscopy, differential scanning calorimetry and X-ray diffraction. We observed that the bent angles of the five-membered heterocyclic substituents are crucial in determining the thermal stability of the LC phases formed, indicating a delicate balance of forces involved in LC phases. The mesophases formed by all symmetrical and unsymmetrical compounds showed thermal stability in the order 1,2-isoxazole > 1,2,3-triazole > 1,2,4-oxadiazole.

New Luminescent Liquid Crystals Based on 2,1,3-Benzothiadiazole and Bent Five-membered N-Heterocyclic Cores

Five new bent-shaped compounds based on the 2,5-disubstituted thiophene central core were successfully synthesised. The lengths of the rigid centres as well as the degree of conjugation were varied by coupling benzene, naphthalene and biphenyl systems to the thiophene through Sonogashira cross-coupling. The thermal, mesomorphic and optical properties of these variants were determined. Compounds 5a,b and 8a displayed liquid-crystalline smectic and nematic mesophases. Strong blue fluorescence was observed for the final compounds.

Thiophene-based bent-shaped luminescent liquid crystals: synthesis and characterisation

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New Luminescent Liquid Crystals Based on 2,1,3-Benzothiadiazole and Bent Five-membered N-Heterocyclic Cores

Thiophene-based bent-shaped luminescent liquid crystals: synthesis and characterisation