New tetrakis(4-aminophenyl)ethenes: synthesis and electrochemical investigations
摘要:
Four novel functional conjugated tetraarylamines containing a tetraphenylenecore were synthesized via Ni-catalyzed aryl amination followed by McMurry olefination. Their electrochemical properties were studied by cyclic voltammetry, coulometry, and electrolysis monitored by UV-vis spectroscopy, and discussed with regard to those of the known tetrakis(dimethylaminophenyl)ethane. (c) 2005 Elsevier Ltd. All rights reserved.
The selective cross McMurry couplings of diaryl or aryl ketones with various substituted ketones were achieved in 53−94% isolated yields. It is believed that the strong affinity of the substituents to the low-valent titanium surface plays an important role in regards to moderating selectivity. Through the introduction of such substituents followed by their removal post McMurry coupling, structurally
The one-pot, cross McMurry coupling between two different diaryl ketones gave structurally varied tetraarylethenes in 59-80% isolated yields. This synthetic protocol is more convenient and effective compared to previously reported procedures