Para-phenylenediamine Schiff base: highly fluorescent photostable solid-state organic dye

Abstract

Schiff bases derived from the condensation of primary amines with aldehydes, such as para-phenylenediamine with salicylaldehyde, exhibit unique optical and structural properties ideal for photonic applications. This study synthesizes such a Schiff base, revealing its properties through detailed HNMR1, FTIR, and XRD characterizations. The compound forms a robust π-conjugated structure, showing a fluorescence emission peak at 560 nm and significant absorbance at 380 nm. A spin-coated laser cavity displayed a critical lasing threshold at 1 MW·cm−2, which could be optimized down to 0.6 kW·cm−2. Moreover, the compounds’ acceptor-donor-acceptor configuration raised outstanding nonlinear optical properties, including a substantial two-photon absorption cross-section of 2×10−11 cm ⋅ W−1·GM, enhancing its utility in high-resolution two-photon imaging and advanced photonic applications. Other nonlinear optical characteristics determined during these studies are the saturable absorption-induced nonlinear absorption coefficient (−2×10−11 cm ⋅ W−1), saturation intensity (2.5×1011 W·cm−2), and Kerr-induced nonlinear refractive index (5×10−16 cm2 ⋅ W−1). The combined linear and nonlinear optical properties, supported by sustained emission and minimal photobleaching under intense re-excitation, establish the para-phenylenediamine Schiff base and derivatives as promising materials for high-brightness, photostable organic light emitters, and solid-state lasers.