A new class of N-annulated perylene tetraesters and their N-alkylated derivatives has been synthesized. N-Annulated perylene tetraesters stabilize a hexagonal columnar phase over a broad temperature range. The hexagonal columnar phase exhibited by these compounds shows good homeotropic alignment with few defects. Annulation in the bay region of the perylene tetraesters enhanced the width of the mesophase compared with the parent tetraesters. N-Alkylation of these compounds perturbed the self-assembly behaviour and the resulting compounds were non-mesomorphic. A bright green luminescence was visible under long wavelength UV light. These properties suggest that these materials may have promising applications in organic electronics.
Perylo[1,12-b,c,d] thiophene tetraesters exhibiting wide-range hexagonal columnar phase have been synthesized. These compounds also exhibit good homeotropic alignment in the liquid-crystalline phase which is very important for the device fabrication. These compounds showed sky-blue luminescence in solution under the long-wavelength UV light. With high solubility and high quantum yield these compounds can serve as standards to measure quantum yields of unknown samples. This new class of materials is promising, considering the emissive nature and stabilization of hexagonal columnar mesophase over a wide thermal range and ease of synthesis.
Selenium-annulated perylene tetraesters that stabilize the hexagonal columnar phase have been synthesized and characterized, and their thermal and photophysical behavior has been determined. The mesophase range decreased with an increase in chain length. A comparative account of the structure-property relationships of this series of compounds with respect to parent perylene tetraesters, N- and S-annulated perylene tetraesters, in terms of their thermal, photophysical and electrochemical behavior is provided. The bay-annulation of perylene tetraesters is a good option to modify the thermal and photophysical properties of perylene derivatives and it can provide a new avenue for the synthesis of several technologically important self-assembling perylene derivatives.
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