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Issue 4, 2019
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Columnar self-assembly, gelation and electrochemical behavior of cone-shaped luminescent supramolecular calix[4]arene LCs based on oxadiazole and thiadiazole derivatives

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Abstract

A new class of blue light-emitting supramolecular liquid crystalline cone or bowl-shaped compounds were synthesized from substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles inbuilt with ester groups containing substituted alkoxy side chains (–OC4H9, –OC8H17) at the lower rim of calix[4]arene. These supramolecular compounds were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), high-temperature X-ray diffraction (XRD), cyclic voltammetry (CV) and photophysical behavior studies. It was observed that the 1,3,4-thiadizole calix[4]arene-based derivatives are more capable of stabilizing the hexagonal columnar phase over a broad thermal range compared to the 1,3,4-oxadiazole calix[4]arene derivatives. The cone-shaped calixarene-based LCs with terminally substituted alkyl chains are packed into columns with enhanced intermolecular interactions. Moreover, the 1,3,4-oxadiazole calix[4]arene derivatives show deeper blue emissions compared to the 1,3,4-thidiazole calix[4]arene derivatives in solution as well as in thin films. The thermal and photophysical behaviors of the synthesized bowl-shaped supramolecular derivatives are extremely dependent on the terminal substituted alkoxy chains on the lower rim of calix[4]arene. Due to their hexagonal columnar phases and the emissive nature of their supramolecular liquid crystal and xerogel states, these molecules are favourable for application in emissive electronic displays. The 1,3,4-thiadiazole calix[4]arene derivatives display lower band gaps than the 1,3,4-oxadiazole calix[4]arene derivatives and are considered to be promising entities for applications in organic light emitting diodes (OLEDs).

Graphical abstract: Columnar self-assembly, gelation and electrochemical behavior of cone-shaped luminescent supramolecular calix[4]arene LCs based on oxadiazole and thiadiazole derivatives

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Publication details

The article was received on 27 Sep 2018, accepted on 09 Dec 2018 and first published on 13 Dec 2018


Article type: Paper
DOI: 10.1039/C8NJ04922J
Citation: New J. Chem., 2019,43, 1910-1925
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    Columnar self-assembly, gelation and electrochemical behavior of cone-shaped luminescent supramolecular calix[4]arene LCs based on oxadiazole and thiadiazole derivatives

    V. S. Sharma, A. P. Shah, A. S. Sharma and M. Athar, New J. Chem., 2019, 43, 1910
    DOI: 10.1039/C8NJ04922J

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