176715-52-9Relevant academic research and scientific papers
Unusual Attractive Au–π Interactions in Small Diacetylene-Modified Gold Clusters
Iwasaki, Mitsuhiro,Shichibu, Yukatsu,Konishi, Katsuaki
, p. 2443 - 2447 (2019)
It is well known that alkynes act as π-acids in the formation of complexes with metals. We found unprecedented attractive Au–π interactions in diacetylene-modified [core+exo]-type [Au8]4+ clusters. The 4-phenyl-1,3-butadiynyl-modifie
Stepwise construction of polyalkene modules grafted on oligopyridine synthons
Ziessel,Suffert
, p. 2011 - 2014 (1996)
We report on the stepwise homologation of the ethynyl substituted pyridine, 2,2'-bipyridine, and 2,2':6',6''-terpyridine with bromoethynyl(triethyl)silane using the Chodkiewicz method. Chelating ligands bearing one or two triethylsilylbutadiyne, one or two triethylsilylhexatriyne subunits have been synthesized and fully characterized.
Are terminal aryl butadiynes stable? Synthesis and X-ray crystal structures of a series of aryl- and heteroaryl-butadiynes (Ar-C≡C-C≡C-H)
West, Kara,Wang, Changsheng,Batsanov, Andrei S.,Bryce, Martin R.
, p. 8541 - 8544 (2007/10/03)
The synthesis and isolation are reported of a range of terminal aryl- and heteroaryl-butadiynes (ArC≡C-C≡CH) 4a-h from 2-methyl-6-(aryl/ heteroaryl)hexa-3,5-diyn-2-ol precursors. The stability of 4a-h in solution is concentration dependent: many of the de
General method for the preparation of alkyne-functionalized oligopyridine building blocks
Ziessel, Raymond,Suffert, Jean,Youinou, Marie-Therese
, p. 6535 - 6546 (2007/10/03)
A large series of alkyne-substituted oligopyridines based on 2,2′-bipyridine, 1,10-phenanthroline, 2,2′:6′,2″-terpyridine, or 1,8-naphthyridine substrates has been synthesized and fully characterized. The palladium(0)-catalyzed coupling of bromo- or chloro-substituted derivatives with (trimethylsilyl)-acetylene proceeds readily in diisopropylamine under ambient conditions giving good yields of the corresponding alkyne-substituted substrates oligoPy(C≡C)SiMe3. The terminal monoynes oligoPyC≡CH become available upon treatment with K2CO3 in methanol. Stepwise homologation of the acetylene function by Cadiot-Chodkiewicz coupling of oligoPyC≡CH with (bromoethynyl)-triethylsilane (BrC≡CSiEt3) affords, in good yield, the silylated diynes oligoPy(C≡C)2SiEt3, from which the terminal diynes oligoPy(C≡C)2H are formed by treatment with aqueous methanolic alkali. Reaction of oligoPy(C≡C)2H with BrC≡CSiEt3 yields the silylated triynes oligoPy(C≡C)3SiEt3 in modest yield. Further homologation is limited by nucleophilic attack of n-propylamine at the C-2 carbon of the alkyne chain, giving rise to a mixture of cis/cis (48%), cis/trans (33%), and trans/ trans (19%) enaminediyne compounds 21a-c. Glaser oxidative self-coupling of the terminal diynes provides access to ditopic bipyridine or terpyridine ligands oligoPy(C≡C)4oligoPy comprising a tetrayne spacer. Quantitative formation of air-stable copper(I) complexes is described for the 6,6′-substituted ligands. A single crystal X-ray structure of complex 22a shows that the two ligands are interlocked around the copper(I) center in a pseudotetrahedral arrangement, similar to the structure deduced from NMR and FAB+ data. The synthetic methods reported herein represent a valuable approach to the large-scale preparation of alkyne-functionalized oligopyridines.
