Oxioative Coupling of 9,10-Dihydrophenanihrene and Polynuclear Hydrocarbons by Aluminum Chloride-Cupric Chloride

Unexpected Oxidation Reaction of 1,6‐Diarylpyrene withCu(BF4)2⋅nH2O Affording Pyrenequinones

“…Oxidative oligomerization reactions of 1 were examined and the results are summarized in Table . Although several reagents were used for the synthesis of the reported pyrenylenes, including AlCl 3 , and H 5 IO 6 , as well as the electrochemical method,,, we have frequently used Cu(BF 4 ) 2 ⋅ n H 2 O in our pyrene chemistry ,,. The standard conditions (entry 1 of Table ) were designed according to our previous studies, i. e ., the reaction with Cu(BF 4 ) 2 ⋅ n H 2 O in nitrile solvent under ambient conditions.…”

Synthesis of sulfonated polynaphthalene, polyanthracene, and polypyrene as strong solid acids via oxidative coupling polymerization

“…Although much work with dehydrogenative condensation has been done with naphthalene, 28-31 a less degree of attention has been paid to higher members such as anthracene [31][32][33][34][35][36][37][38][39][40][41] and pyrene. 36,[42][43][44] It has been briefly mentioned that anthracene reacted with FeCl 3 in a fused mixture or in carbon tetrachloride to yield the chlorinated polymer. 45 Table II summarizes the results for elemental analyses of PAT.…”

“…Few reports on the synthesis of PPR exist because of the difficulty of polymerization. It has been reported that 1,1 0 -bipyrene was produced by the treatments of pyrene with SbCl 3 -AlCl 3 , 36 AlCl 3 -CuCl 2 , 44 and periodic acid in acetic acid. 42 Recently, PPR was synthesized by chemical oxidative polymerization of pyrene with FeCl 3 in hexane-nitromethane and the results indicated that PPR was formed mainly through dehydrocoupling between (2-or 1-) and (2 0 -or 1 0 -) positions on the pyrene ring.…”

“…Existence of the broad diffraction peak (2y ¼ 5-15 ) suggests that PPR indeed consists of the pyrene repetitive units. 46,51 The weak broad diffraction peak (2y ¼ [35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] is owing to the a axis of the graphite structure. 11,17,18,49 The larger broad diffraction peak (2y ¼ 5-15 ) compared with those of PAT and PNP indicates that larger content of the pyrene repetitive units was involved.…”

Novel highly stable semiconductors based on phenanthrene for organic field-effect transistors

“…The structures of oligomers, i.e. 2,29;79,20-terphenanthrenyl (Ph3) 10 and 5,59-bis(phenanthren-2-yl)-2,29-bithiophene (PhT2), are depicted in Fig. 1.…”