0000000000178668
AUTHOR
Sabine Hillmann
Tris[oligo(1,4-phenylenevinylene)]methylium Dyes
The tris[oligo(1,4-phenylenevinylene)]carbinols 2a–f (n =1–4) and the tris(4-styrylphenyl)methanes 7a,b have been prepared by Wittig–Horner (3 + 4a–f 2a–f) and Siegristreactions (5 + 6a,b 7a,b). The Wittig–Horner reactions in these examples are accompanied by an autoxidation, whereas a reduction occurs in the Siegrist reactions. Compound 2a, the lowest member (n = 1) of the series 2a–d with terminal dialkylamino groups, generates first, on treatment with acids, the methylium dye 2′a, which absorbs far into the NIR region (λmax = 1100 nm). The higher members 2b,c (n = 2,3) of the carbinol series yield by acidic treatment only N-protonated methylium dyes 2″′b,c. The different behavior is due …
ChemInform Abstract: Synthesis of Highly Substituted Hexahelicenes
C2-Symmetric hexahelicenes 3a–3g, which bear four or six alkoxy chains, were prepared in eight-to-nine reaction steps in high overall yields. The final step consisted of a twofold oxidative photocyclization of the corresponding 2,7-bis(2-phenylethenyl)naphthalenes. Long (and branched) chains provide a good solubility and processability, which is a prerequisite for applications in organic synthesis and materials science.
Photochemistry of 3,6-bis(styryl)pyridazines in solution and in neat liquid crystalline phase—optical switching and imaging techniques
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 ph…
Optical Switching and Antenna Effect of Dendrimers with an Anthracene Core
Dendrimers 6G(i) (i=1-4) consisting of an anthracene core and Fréchet dendrons which are attached via a CH(2)OCH(2) chain in the 9-position undergo quantitative and completely reversible intramolecular [4pi+4pi] cycloaddition. The process can be monitored by absorption and fluorescence measurements. The Fréchet dendrons act as an energy funnel that collects and focuses the photon energy but does not change the photostationary states, which for both directions are completely on the product side when the separate chromophores are selectively irradiated. The quantum yields of anthracene fluorescence and of singlet energy transfer from the dendrons to the core were studied as a function of dend…