Aldehyde‐functionalised distyrylbenzene: Photophysical properties and primary amine sensitivity evaluation in solution and solid state

Abstract

The identification of amines is a highly beneficial process in the industrial sector; food corruption, including fish and shellfish and, more importantly, breathing amines, causes dangerous illnesses. In this study, the optical properties and amine sensing of a π‐conjugated organic compound, 1,4‐bis[4‐formylstyryl]benzene (BFSB), containing two aldehyde functional groups, was investigated. BFSB showed ultraviolet–visible absorption in the range of 318‐329 nm with a high molar extinction coefficient (ε = 2.21*105–2.83*105 M−1 cm−1) in the tested solvent with different polarities. BFSB emits in the visible spectrum (420‐514 nm) with Stokes shifts of ca. 6678‐11 991 cm−1. Density functional theory at the B3LYP/6–31 ++ G level of calculation was employed to evaluate the molar structures and frontier orbitals. The combination of BFSB with poly(methyl methacrylate) and polyvinyl alcohol polymers exhibits different photophysical properties. Interaction of this dye with various primary amines in both solution and solid forms leads to the quick formation of an imine group (the reaction of aldehyde with amine and then dehydration). A hypsochromic shift was observed upon treatment of amine with BFSB.