80731-20-0Relevant academic research and scientific papers
On the trimerization of cyanoacetylene: Mechanism of formation of tricyanobenzene isomers and laboratory detection of their radio spectra
Hopf, Henning,Mlynek, Cornelia,McMahon, Robert J.,Menke, Jessica L.,Lesarri, Alberto,Rosemeyer, Michael,Grabow, Jens-Uwe
scheme or table, p. 14115 - 14123 (2011/02/22)
In support of a deeper understanding of the chemistry of cyanoacetylene-a known constituent of planetary atmospheres and interstellar space-theoretical and experimental studies address the chemical mechanism of dimerization and trimerization, and provide high-resolution rotational spectra of two of the trimeric products, 1,2,3- and 1,2,4-tricyanobenzene. Analysis of the rotational spectra is particularly challenging because of quadrupolar coupling from three 14N nuclei. The laboratory rotational spectra provide the basis for future searches for these polar aromatic compounds in interstellar space by radio astronomy.
Excited State Luminescence of Multi-(5-phenyl-1, 3, 4-oxadiazo-2-yl) benzenes in an Electron-Donating Matrix: Exciplex or Electroplex?
Yang, Chih-Chiang,Hsu, Chia-Jung,Chou, Pi-Tai,Cheng, Hsu Chun,Su, Yuhlong Oliver,Leung, Man-Kit
experimental part, p. 756 - 768 (2010/06/21)
Multi-(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzenes show emission in organic solvents from ultraviolet to blue (339-447 nm). The reduction potentials E 1/2red cover a large range of -2.11 V for 2, 5-diphenyl-1, 3, 4-oxadiazole to -0.76 V for 1, 2, 3, 4, 5, 6-hexa(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzene. An unexpectedly wide spectral range of the oxadiazole (OXD) exciplex emissions in PVK is observed, ranging from 406 to 603 nm. The OXDs also exhibit similar electroluminescence (EL) when blended into polyvinylcarbazole (PVK). A linear correlation between the λ max of the electroluminescence and photoluminescence is observed, implying that the emission mechanisms in both processes are similar. In addition, the linear correlation between the E1/2red versus λmax of EL (eV) reflected that the term of the charge-transfer configuration of the contact electron-hole pair plays a major role in the exciplex emission. The exciplex EL of 1, 2, 5-tri(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzene (5) could be as high as 1.0 cd/A. Since the exciplex emission usually has a large Stokes shift, this provides a window for us to generate duo emissions for near white light EL with high efficiency. Among the devices we tried, the device of PVK/2-tert-butylphenyl-5-biphenyl-1, 3, 4-oxadiazole/5/2, 5, 8, 11-tetra-tert-butylperylene (100:40:40:4) gave EL with good current efficiency of 1.63 cd/A.
Photochemical cycloaddition reactions of cyanoacetylene and dicyanoacetylene.
Ferris,Guillemin
, p. 5601 - 5606 (2007/10/02)
Photolysis of cyanoacetylene with 185- or 206-nm light yields 1,3,5-tricyanobenzene while 254-nm radiation yields a mixture of tetracyanocyclooctatetraenes, 1,2,4- and 1,3,5-tricyanobenzene. A polymer of cyanoacetylene is the major photoproduct. 1,3,5-Tricarbomethoxybenzene was the only photoproduct identified from the irradiation of methyl propiolate at 254 nm. Mono-, di-, and tricyanobenzenes are formed by irradiation of mixtures of acetylene and cyanoacetylene at 185, 206, and 254 nm along with trace amounts of cyclooctatetraenes. No photoadducts were detected on photolysis of mixtures of cyanoacetylene and CO or HCN. The tetracyanocyclooctatetraene structures were established by UV, MS, and NMR analyses. The 1H NMR of the product mixture exhibited a singlet at delta 7.028 consistent with either 1 or 2 and two singlets at delta 6.85 and 6.91 assigned to 3. Photolysis of mixtures of dicyanoacetylene and acetylene with either 185- or 206-nm light yielded 1,2-dicyanobenzene and (E,Z)-1-buten-3-yne-1,4-dicarbonitrile. These products were also obtained using 254-nm light along with a mixture of tetracyanocyclooctatetraenes. The same three singlets were observed in this product mixture as were observed in the tetracyanocyclooctatetraenes obtained from cyanoacetylene. From this observation it was concluded that the delta 7.02 signal is due to 2 and not 1. The photolysis of cyanoacetylene and dicyanoacetylene in the presence of ethylene with 185-nm light yields 1-cyanocylobutene and 1,2-dicyanocyclobutene, respectively. 2-Cyanobutadiene and 2,3-dicyanobutadiene are the photoproducts with 254-nm light. Reaction pathways are proposed to explain these findings.
