stilbene

Stilbene is an organic compound consisting of two phenyl rings connected by a central carbon–carbon double bond, giving the formula C14H12. It exists as geometric isomers, with trans-stilbene (E-stilbene) being the thermodynamically more stable form and cis-stilbene (Z-stilbene) being less stable. The trans isomer can convert to the cis form under certain conditions, such as exposure to ultraviolet light, and the two forms have distinct physical properties.

Stilbene and many of its derivatives occur in nature in small quantities and are studied as motifs in plant secondary metabolism. The family includes assorted hydroxylated and methoxylated variants; resveratrol is a well-known natural stilbene derivative that has drawn significant scientific attention for its biological activity. Beyond natural products, the stilbene framework is widely used in dye chemistry, organic electronics, and as a versatile building block in polymer and materials science.

Applications and representations: Stilbene compounds have been explored for their nonlinear optical properties and as components in scintillators and other photonic materials. They are also used as precursors to dyes and as starting points in the synthesis of various polymers and functional molecules. The high degree of conjugation in stilbene systems underpins many of these applications, particularly in optoelectronic contexts.

Synthesis and isomerization: Stilbene can be prepared by several synthetic routes. A common laboratory method is the McMurry coupling of benzaldehyde to give trans-stilbene. Other approaches include various olefination strategies, such as Wittig- or Horner–Wadsworth–Emmons-type reactions, which assemble the C=C linkage between aryl fragments. The trans isomer is usually obtained preferentially, with photochemical or thermal processes used to access the cis form when desired.