New azomethine-phthalic diimides: Synthesis and thermal, optical and electrochemical characterization

A new diamine with phthalic diimide moiety, i.e. N,N′-bis(4-amino-2,3,5,6-tetramethylphenyl)phthalene-1,4-dicarboxyimide was synthesized and applied for condensation with 4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)benzaldehyde and 4-octadecyloxybenzaldehyde, which resulted in two new azomethine-phthalic diimides (AZ-PDIs). Thermal, optical and electrochemical properties of AZ-PDIs were discussed in relation to their analogous containing instead of five-membered six-membered imide rings (AZ-NDIs) described in our previous work. The phase behavior of AZ-PDIs examined by differential scanning calorimetry (DSC) and polarized optical microscopy (POM) confirms their liquid crystalline properties in wide range of temperatures. AZ-PDIs do not show decomposition below 400 °C as was found based on thermogravimetric analyses (TGA). Optical properties of the prepared compounds were investigated by UV–vis and photoluminescence (PL) measurements. Azomethine-phthalic diimides emitted blue light with emission maximum (λem) at ca. 446–492 nm contrary to azomethine-naphthalene diimides which emitted green light and λem was at 536 and 540 nm. The obtained compounds are electrochemically active and undergo reversible reduction and oxidation as evidenced by differential pulse voltammetry (DPV). The azomethine-phthalic diimides exhibited low electrochemical band gap ca. 1.68 eV being promising for optoelectronic applications.