Diacetylene 10,12-pentacosadiynoic acid

Keywords diacetylene, nanocrystalline Ti02, 10,12-pentacosadiynoic acid... 

Poly diacetylene (44a-c) (Figure 3.1.16) derivatives have been synthesized and tested in OTFTs. A hole mobility of 1.3 x 10 cmVvs and an on/off ratio of 10" were reported for 44a, the polydiacetylene prepared from 10, 12-pentacosadiynoic acid.[257]... 

During the late 1960s, Wegner reported that single-crystalline diacetylenes could be topochemically polymerized to ene-yne polydiacetylenes [78], and several groups subsequently applied this chemistry to crosslinking polymerizations in 2-D confinement. For example, Leblanc synthesized the dendrimer-based amphiphile 34 in which sixteen 10,12-pentacosadiynoic acid chains were coimected to the periphery of a third-generation poly(amidoamine) (PAMAM) dendrimer [79]. A monolayer of this dendritic amphiphile was prepared at the air/water interface, in which the... 

Diacetylene fatty acids were purchased from GFS. N-(2-Hydroxyethyl)-10,12-pentacosadiynamide (10) was synthesized by literatnre methods (77). 1-Amino-10,12-pentacosadiyne (11) was synthesized in fom steps from 10,12-pentacosadiynoic acid the acid in anhydrous tetrahydrofuran (THF) at 0 °C was reduced to the alcohol through treatment with hthinm alnminnm hydride (LAH, 2.5 equivalents) in diethyl ether for two hours, the alcohol was then converted to the mesylate by treatment with mesyl chloride (6 eqnivalents) in methylene chloride with diisopropyl ethyl amine over 30 minntes, the mesylate was displaced by sodium azide (1.5 equivalents) in dimethyl formamide (DMF) at 70 °C over one hour and the azide, in THF, was reduced to the amine with LAH (2 equivalents) in diethyl ether at 0 °C over one hour. N-(10,12-pentacosadiynyl)-glutamic acid (12) was prepared from 11 as follows 11 was reacted with glutaric anhydride (2 equivalents) in DMF, in the presence of diisopropylethylamine (3 equivalents), at 70 °C for 1 hour and the crade product recrystallized from a mixture of chloroform and hexanes. The identity of products were confirmed by H and C NMR. 

---