Tieffarbige aromatische Fünfringketone. [Heteropolare, XXVII]

Synthesis and conducting and thermal properties of polysilanes containing substituted benzophenanthrene groups

“…Dichloromethylvinylsilane and 2,5-diphenyl-3,4-(o,o 0 -biphenylene)cyclopentadienone were reacted in toluene in a sealed tube at 2308C for 10 h, the solution turned from black green to yellow, and 1 was obtained. Its structure was confirmed by IR and 1 H-, 13 C-, and 29…”

“…2,5-Diphenyl-3,4-(o,o 0 -biphenylene)cyclopentadienone was prepared according to the literature. 13 Synthesis of dichloromethyl (2,9-diphenyl-7,8-benzophenanthryl)silane (1) Dichloromethylvinylsilane (8.4 g, 0.06 mol), 150 mL of toluene, and 15.3 g (0.04 mol) of 2,5-diphenyl-3,4-(o,o 0 -biphenylene)cyclopentadienone were sealed in an evacuated glass tube and heated in a hydrogenation bomb at 2308C for 10 h. After the tube was cooled and opened, the toluene and volatile silicone compounds were evaporated. The residue was purified by a silica gel column under N 2 protection, with drying toluene as the eluent, to give the pure product.…”

“…Poly [methylphenylsilylene-co-(2,9-diphenyl-7,8-benzophenanthryl)methylsilylene] (PMBSI) was obtained by Wurtz-type coupling of dichloromethylphenylsilane and 1 and was characterized with Fourier transform infrared, 1 H-NMR, 13 C-NMR, 29 Si-NMR, gel permeation chromatography, and ultraviolet and fluorescence spectroscopy. The conducting properties and thermal properties of the polymer were investigated.…”

A Superior Synthesis of Longitudinally Twisted Acenes

“…Ac onvenient quinone precursorf or pentacene 2 is 9,11,20,22-tetraphenyltetrabenzo[a,c,l,n]pentacene-10,21-dione [21,22] (5), which is known and typically preparedb yt he double addition of phencyclone [23][24][25] (6)t o one-half equivalent of p-benzoquinone. But as illustrated in Scheme 2, it may also be prepared by the condensation of the previously reported 9,14-diphenylbenzo[f]tetraphene-10,13-dione [26] (7)w ith 6 in 36 %y ield.…”

“…The overall yield of acene 14 from phencyclone (6)w as 6.6 %, an almost 66-fold improvement over its original synthesis. Condensation of dienone 7 with the easily prepared acecyclone [23] (15) Orange crystals of acene 17 suitable for X-ray analysis were grown from EtOAc-CH 2 Cl 2 ,a nd its molecular structure is showni nF igure 4. Acene 17 crystallizes in the monoclinic space group P2 1 /n,w ith Z = 4.…”