New triphenylamine-based oligomeric Schiff bases containing tetraphenylsilane moieties in the backbone

Abstract

Three new triphenylamine-based oligomeric Schiff bases (polySB1, polySB2 and polySB3) containing tetraphenylsilane core (TPS-core) in the main chain were obtained from TPS-core-based diamines and bis(4-formylphenyl)phenylamine by a high-temperature polycondensation reaction. These new oligomers were structurally characterized by FT-IR, NMR and elemental analysis. All polySBs were highly soluble in common organic solvents, such as chloroform, tetrahydrofuran and chlorobenzene. Samples showed moderate molecular average molecular weight (Mw) and a high thermal stability above 410 °C. Likewise, polySBs showed absorption near 400 nm in the UV-vis range and photoluminescence. The HOMO levels and band-gap values were found in the ranges of -6.06 to -6.18 eV and 2.65-2.72 eV, respectively. The lowest band-gap value was observed for polySB2, which could be attributed to a more effective p-conjugation across the main chain. The results suggest that silicon-containing polySBs are promising wide-band-gap semiconductors materials for optoelectronic applications.