86239-14-7Relevant academic research and scientific papers
Proaromaticity: Organic charge-transfer chromophores with small HOMO-LUMO gaps
Wu, Yi-Lin,Bures, Filip,Jarowski, Peter D.,Schweizer, W. Bernd,Boudon, Corinne,Gisselbrecht, Jean-Paul,Diederich, Francois
scheme or table, p. 9592 - 9605 (2010/10/19)
Novel donor- and/or acceptor- substituted cross-conjugated carbocycles based on quinoids or expanded quinoids, with radiaannulene perimeters, were prepared and investigated to validate proaromaticity as a concept for reducing HOMO-LUMO gaps in push-pull chromophores. Analyses of IR, 1H NMR, and UV/Vis/NIR spectra in conjunction with molecular structures determined by X-ray diffraction show that these push-pull quinoids have significant charge-separated ground states. This feature results in small optical gaps (near IR region) and diatropic magnetic environments inside the carbocycles, as suggested by nucleus- independent chemical shift (NICS) calculations. The NICS results, together with the bond-length analysis of the quinoid spacers, provide strong support that proaromaticity, that is, aromatized zwitterionic mesomeric contributions in the ground state, is effective. A push-pull tetrakis(ethynediyl)- expanded quinoid chromophore represents the first proaromatic radiaannulene.
A NEW APPROACH TO ARYLMALONONITRILES
Yamaguchi, Shunro,Araki, Hisashi,Hanafusa, Terukiyo
, p. 685 - 688 (2007/10/02)
Arylmalononitriles were prepared from the corresponding benzoyl chlorides by three reaction steps.Treatment of the starting substances with cyanotrimethylsilane in the presence of pyridine gave dicyanotrimethylsiloxymethylbenzenes, which were transformed
A NEW ROUTE TO PHENYLENEDIMALONITRILE AND THE ANALOGUES USING PALLADIUM-CATALYZED CARBON-CARBON BOND FORMATION
Uno, M.,Seto, K.,Masuda, M.,Ueda, W.,Takahashi, S.
, p. 1553 - 1556 (2007/10/02)
Phenylenedimalonitrile and the analogues, which are key intermediates in the synthesis of TCNQ and the analogues, are prepared directly by the Pd-catalyzed reaction of diiodoarenes with malononitrile anion.
