Electrosynthesis and characterization of a poly(paraphenylene) deriving from p-fluoroanisole

Electrosynthesis and structural characterization of a novel aryl ether trimer

“…From the third to the fifth cycle, the accessible anodic potentials became higher and two closely spaced waves appeared in the potential range of A 3 , between 2.0 and 2.7 V. However, when the potential sweep was reversed only one complementary negative peak was observed. The appearance of cross-over phenomenon and loss of the reproducibility have been described in the anodic oxidation of m-methoxytoluene [19] and p-fluoroanisole [11], at high concentration. They have been explained by the occurrence of surface phenomena due to the formation of heavy products such as dimer, trimer and polymer.…”

“…This compound has been previously synthesized by a copper coupling reaction of 2-iodo-p-tert-butyl anisole [24]. It is worth noting that this dimer is the symmetric one, resulting from an ortho-ortho coupling, in contrast with the dimer obtained from p-methyl anisole [11][12]. For triphenyl type trimer the retention time in G.C.…”

“…At the surface of electrodes, radical cations generated by oxidation of alkylbenzenes can lead to the formation of diphenyl and, or diphenylmethane derivatives [3][4][5][6]. In the case of aryl ethers, several studies have been devoted to the anodic dimerization [7][8][9][10][11]. The anodic trimerization has been reported in the case of p-fluoroanisole [11].…”

“…In the case of aryl ethers, several studies have been devoted to the anodic dimerization [7][8][9][10][11]. The anodic trimerization has been reported in the case of p-fluoroanisole [11]. Ortho-dialkoxybenzenes undergo an unusual oxidation to lead triphenylenes [12].…”

The anodic reactivity of 4,4′-dimethoxychalcone: a synthetic and mechanistic investigation

“…We demonstrated that the coupling of the radical cations issued from the first electron transfer was the governing reaction near the electrode. Particularly, under anhydrous conditions, successive coupling reactions, according to an (EC)n mechanism, led to conjugated oligomers from the polyphenylene family [3][4][5][6][7][8]. The methoxy group plays a crucial role in decreasing the oxidation potential and in the distonic character displayed by the generated radical cations.…”