perylene

Perylene is a polycyclic aromatic hydrocarbon (PAH) with the formula C20H12. It consists of five fused benzene rings arranged in a compact, peri-fused, planar skeleton. The molecule is highly conjugated and has a rigid, flat structure, which contributes to its chemical stability and distinctive photophysical properties. Perylene is hydrophobic and has limited solubility in water, but dissolves in a range of organic solvents to give solutions or form crystalline solids.

Perylene occurs in trace amounts in coal tar and can be produced synthetically for research and industrial use. It serves as a building block and reference compound in studies of PAHs and fluorescence due to its well-defined structure and strong, characteristic emission. While the parent hydrocarbon itself has limited direct applications, its derivatives are of major commercial importance.

Derivatives of perylene, notably perylene-3,4-dicarboximide and related diimide dyes, are widely used in organic electronics and materials science. Perylene diimide dyes are valued for their strong absorption, excellent photostability, and favorable electronic properties, making them common components in organic light-emitting diodes, organic photovoltaics, and fluorescent labeling. The chemistry of these derivatives is a major area of research, enabling tunable optical and electronic performance.

Safety and environmental notes: as a PAH, perylene and many of its derivatives warrant careful handling to minimize inhalation or dermal exposure. They are typically treated as persistent environmental contaminants and should be managed according to applicable regulations and safety guidelines.