New room-temperature thermotropic perylene-based bisimides: Synthesis, liquid crystalline, light-emitting and electrochemical properties

Three N-alkoxy-substituted perylene-3,4,9,10-tetracarboxyldiimides (PBIs) were synthesized and characterized through the data from 1H nuclear magnetic resonance (NMR), infrared spectroscopy (IR), elemental analysis, UV–vis absorption spectroscopy, photoluminescence (PL), cyclic voltammetry (CV) and differential pulse voltammetry (DPV) measurements. The phase behavior of obtained bisimides was examined by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). They possess liquid crystalline properties at room temperature and a single mesophase structure exists in wide range of temperatures. The presented bisimides are well soluble in common solvents. All of them are highly fluorescent in solution and in solid state as blend with PMMA. The electrochemical band gap energy (Eg), LUMO and HOMO energy values were in the range 1.46–2.11 eV, −3.74 to −3.98 V and −5.38 to −5.96 V, respectively.

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► We obtained new room-temperature thermotropic perylene bisimides.
► They are highly soluble in common solvents.
► Their electrochemical energy band gap was in the range 1.46–2.11 eV.
► These compounds seems to be promising potential candidates for optoelectronics.