70437-06-8Relevant academic research and scientific papers
Synthesis and characterization of propeller-shaped mono- to hexacationic quinolinium-substituted benzenes
Batsyts, Sviatoslav,Hübner, Eike G.,Namyslo, Jan C.,Gjikaj, Mimoza,Schmidt, Andreas
, p. 4102 - 4114 (2019/04/30)
Diels-Alder reaction of 2-, 3- and 4-(phenylethynyl)quinolines and tetraphenylcyclopentadienone gave three regioisomeric 2,3,4,5,6-pentaphenyl-1-(quinolin-2-yl, -3-yl, and -4-yl)benzenes. Restricted rotation of the 3-yl and 4-yl substituted derivatives is observed between the central core and the substituents, resulting in propeller-shaped molecules. Likewise, 1,2-diquinolinyl-3,4,5,6-tetraphenylbenzenes with 3-yl,3-yl and 3-yl,4-yl connectivity were prepared. As evidenced by NMR spectroscopy, they form two diasteromers due to their restricted rotation. A cobalt-catalyzed [2 + 2 + 2]-cyclotrimerization of 2-(phenylethynyl)quinoline resulted in the formation of triphenyl-2,4,6- and -3,5,6-tri(quinolin-2-yl)benzenes. The same reaction was applied to 3,3′-ethyne-1,2-diyldiquinoline which formed hexa(quinolin-3-yl)benzene. N-Methylation gave the title compounds. Among those, the hexacationic hexa(N-methylquinolinio-3-yl)benzene is described. Stereochemical aspects are predominantly discussed by means of results of NMR experiments. DFT-calculations on the most stable conformations and the frontier orbital profiles of the hexacation as well as of its neutral precursor have been carried out.
Synthesis and electrogenerated chemiluminescence of donor-substituted phenylquinolinylethynes and phenylisoquinolinylethynes: Effect of positional isomerism
Elangovan, Arumugasamy,Yang, Shu-Wen,Lin, Jui-Hsien,Kao, Kuo-Ming,Ho, Tong-Ing
, p. 1597 - 1602 (2007/10/03)
In furtherance of our research on the design, synthesis and study of electrogenerated chemiluminescence (ECL) of new donor substituted phenylquinolinylethynes, we report here more new series with the aim of studying the effect of positional isomerism on their overall photophysical properties with a special focus on ECL. For this study we have chosen 2-, 3-, and 4-(p-substituted phenyl)ethynylquinolines, and 1- and 4-(p-substituted phenyl)ethynylisoquinolines. These ethynes were synthesized in good yields by modified Sonogashira coupling of the corresponding terminal alkyne with the respective haloquinolines. The photophysical properties and ECL were studied in acetonitrile solvent and the various results are discussed.
Palladium-phosphinous acid-catalyzed Sonogashira cross-coupling reactions in water
Wolf, Christian,Lerebours, Rachel
, p. 2161 - 2164 (2007/10/03)
A palladium-phosphinous acid-catalyzed Sonogashira cross-coupling reaction that proceeds in water under air atmosphere in the absence of organic co-solvents has been developed. Disubstituted alkynes have been prepared in up to 91% yield by POPd-catalyzed
