Stilbenes Synthesis and Applications

Abstract

Stilbenes and their derivatives, stilbenoids, form a multidisciplinary field that combines many important branches of chemistry, biology, and physics. The number of publications on stilbenes available on the Internet has reached approximately 32,000. Classical and modern synthetic organic chemistry (more than 6300 articles) provide a whole arsenal of stilbenes of different structures. The unique features of this class of compounds, including a combinatihon of fluorescence, phosphorescence, photochrome, photochemical, and photophysical properties, are paving the way for numerous fundamental research and practical applications. Specifically, ( 1 ) stilbenes are used as dyes, brighteners, whiteners of paper and textile, and photobleachers; ( 2 ) stilbenes and its combination with polymers and inorganic materials have been made as a basis for numerous optical and measuring instruments, devices, and apparatuses for dye lasers, organic solid lasers, and scintillators, phosphorus, neutron, and radiation detectors, electrophotographic photoconductor and image‐forming apparatus, and photochromic, light‐transmitting, dichroic, electroluminescent nonlinear optic, and organic–inorganic hybrid multichromophoric optical limiting materials; ( 3 ) stilbenoids are naturally present in plants and have been used as drugs and antitumor agents; and ( 4 ) stilbene derivatives have been used as molecular probes and labels for investigation of structure and dynamic properties of proteins and biomembranes. This article concisely covers the main aspects of stilbenes synthesis, chemical activity, and application.

Supported Palladium on Magnetic Nanoparticles–Starch Substrate (Pd-MNPSS): Highly Efficient Magnetic Reusable Catalyst for C–C Coupling Reactions in Water

“…Subsequently, the generality and limitation of the methodology were analyzed using different coupling partners under optimized conditions (Scheme ). First, styrenes were reacted with aryl halides, and some different stilbenes were synthesized. Both electron-rich and electron-poor aryl halides gave satisfactory yields.…”

Multifunctional Optical Polymeric Films with Photochromic, Fluorescent, and Ultra‐Long Room Temperature Phosphorescent Properties

“…[ 1 ] Photochromism, which can be interconverted between two isomeric states with distinct chemical structures upon light irradiation, is an interesting optical phenomenon and has wide practical applications in the fields of nanomachines and smart molecule switches. [ 2 ] The typical photochromic molecules include azobenzenes, [ 3 ] stilbenes, [ 4 ] dithienylethenes, [ 5 ] spiropyrans, [ 6 ] and naphthopyrans. [ 7 ] Fluorescence, which is produced by the radiative transition from the singlet excited state to the ground state, [ 8 ] has been used extensively in the fields of fluorescent labelling [ 9 ] and chemical detectors.…”

Toxicological Evaluation of Piceatannol, Pterostilbene, and ε-Viniferin for Their Potential Use in the Food Industry: A Review

“…Natural stilbenes are secondary metabolites produced by plants to protect themselves against stressful conditions such as ultraviolet irradiation, excessive heat and fungal or bacterial infections [ 2 ]. Structurally, stilbenes are characterized by the presence of a 1, 2-diphenylethylene nucleus [ 4 ] and they can be found in E, or trans, and Z, or cis configurations, the trans form being the one that exhibits more potent pharmacological activities [ 5 , 6 ]. Moreover, these compounds exist as monomers, such as resveratrol, piceatannol, or pterostilbene, and oligomers, like ε-viniferin [ 1 ] ( Figure 1 ).…”

“…These compounds have been widely used in the manufacture of industrial dyes, laser dyes, optical brighteners, phosphors, and scintillators [ 5 ]. However, in recent years, stilbenes and their analogues have awakened the interest of the scientific community due to their diverse spectrum of biological applications such as anticarcinogenic, antiproliferative, antiangiogenic, antimicrobial, antileukemic, anti-inflammatory, antioxidant, antimutagenic, and antigenotoxic agents, and as a vasodilator [ 2 , 10 , 11 ], among others [ 6 ].…”