the problem of oxidation is to replace the hydrogens ortho to the carbon-carbon double bond by groups that can not be removed during the oxidation. Following the Woodward–Hoffmann rules, the photochemical 6π cyclization takes place in a conrotatory fashion, leading to products with an anti configuration of the methyl substituents. As both methyl groups are attached to a stereogenic center, two enantiomers (R,R and S,S) are formed, normally as a racemic mixture. This approach also has the advantage that the thermal (disrotatory) ring closure can not take place because of steric hindrance between the substitution groups. Dithienylethenes Ortho-substitution of the aromatic units results in a stabilization against oxidation, but the closed-ring form still has a low thermodynamic stability in most cases (e.g. 2,3-dimesityl-2-butene has a half-life of 90 seconds at 20°C). This problem can be addressed by lowering the aromaticity of the system. The most commonly used example are the dithienylethenes, i.e. alkenes with a thiophene ring on either side. Dithienylethene derivatives have shown different types of photochemical side reactions, e.g., oxidation or elimination reactions of the ring-closed isomer and formation of an annulated ring isomer as a byproduct of the photochromic reaction. In order to overcome the first, the 2-position of the thiophenes is substituted with a methyl group, preventing oxidation of the ring closed form. Also often the two free α-positions on the double bond are connected in a 5 or 6-membered ring in order to lock the double bond into the cis-form. This makes the dithienylethene undergo only open-closed ring isomerization, unconfused by E-Z isomerization. More recently, based on recent findings showing that by-product formation most likely occurs exclusively from the lowest singlet excited state, a superior fatigue resistance of dithienylethenes upon visible-light excitation has been achieved by attaching small triplet-sensitizing moieties to the diarylethene core via a -conjugated linkage. The dithienylethenes are also of interest for the fact that their isomerization requires very little change of shape. This means that their isomerization in a solid matrix can take place much more quickly than with most other photochromic molecules. In the case of some analogs, photochromic behavior can even be carried out in single crystals without disrupting the crystal structure. Applications Typically, the open-ring isomers are colorless compounds, whereas the closed-ring isomers have colors dependent on their chemical structure, due to the extended conjugation along the molecular backbone. Therefore, many diarylethenes have photochromic behavior both in solution