6533b837fe1ef96bd12a26f9
RESEARCH PRODUCT
Photochemistry of 3,6-bis(styryl)pyridazines in solution and in neat liquid crystalline phase—optical switching and imaging techniques
Thorsten LifkaHerbert MeierAnnette OehlhofPeter SeusSabine Hillmannsubject
Quenching (fluorescence)Liquid crystalChemistryPhotostationary statePhase (matter)Organic ChemistryDrug DiscoveryAlkoxy groupSinglet statePhotodegradationPhotochemistryBiochemistryThermotropic crystaldescription
Abstract 3,6-Bis(styryl)pyridazines 1a – f with 2–6 alkoxy groups show on irradiation in solution a stereoisomerization which leads to a photostationary state of ( E , E )- and ( E , Z )-isomer. Sensitizing and quenching experiments reveal that the ( E , E )→( E , Z ) route is a pure triplet process, whereas the ( E , Z )→( E , E ) route can have a minor singlet by-reaction. Hexyloxy or dodecyloxy chains on the terminal benzene rings convey the ( E , E )-isomers of compounds 1a , b , d – f thermotropic liquid crystalline properties. In particular S A , S C , and S F/I phases were studied with regard to their photochemical behavior. Depending on the system, photodegradation of the smectic phase to the isotropic melt (S→I) or photoinduction of the smectic phase (I→S) can be achieved by alteration of the ( E , E )/( E , Z ) ratio. These processes represent the basis for imaging techniques (writing and erasing of information).
year | journal | country | edition | language |
---|---|---|---|---|
2008-11-01 | Tetrahedron |