Derivatives of 1,8-diphenylanthracene

Abstract

Two additional polyphenylated anthracenes, the 1,8,10-triphenyl derivative 5 and the 1,8,9,10-tetraphenyl derivative 6, have been prepared by reaction of the diphenylquinone 2 with phenyllithium followed by reduction and dehydration. Mononitration of 1,8-diphenylanthracene (Id) yielded the 10-nitro derivative 13. Derivatives 12 of 1,8-diphenylanthracene with a substituent at C-9, a location allowing interaction of the substituent with the orbitals of the two phenyl rings, were obtained by the methylation or acetylation of the anthrone 11. Studies of the oxidation and reduction of the various hydrocarbons 1, 5, 6, and 20 by polarography and cyclic voltammetry provided a measure of the relative ease of adding or removing one or more electrons from these hydrocarbons. In general, the cation radicals and dianions formed were relatively unstable, but the anion radicals had substantial lifetimes even in partially aqueous solutions.

(2,1‐a)‐Indenofluorene Derivatives: Syntheses, X‐ray Structures, Optical and Electrochemical Properties

“…Indeed, when the phenyl rings are pstacked the oxidation potential of the anthracenyl core is lower (1.30 V/SCE) than when phenyl rings are not pstacked (1.34 V/SCE). [68] A second oxidation process (isoelectronic to the first) and a third oxidation process are observed for ( 6 ] 0.1 m) presents two successive redox waves with maxima at À2.48 and À3.00 V, respectively, the first being twice in intensity compared to the second (see CV and DPV in Supporting Information).…”

“…(1,2-b) [67] A C H T U N G T R E N N U N G (2,1-a) [27] A C H T U N G T R E N N U N G tives where the phenyl rings can either be in a close face-toface arrangement or not. [68] Thus, the oxidation potential of the anthracenyl core seemed to be influenced by the different electronic effects caused by the different arrangements of the phenyl rings. Indeed, when the phenyl rings are pstacked the oxidation potential of the anthracenyl core is lower (1.30 V/SCE) than when phenyl rings are not pstacked (1.34 V/SCE).…”

Fluorophore Release from a Polymethinic Photoremovable Protecting Group Through a Nonlinear Optical Process

“…Scheme shows the method used for the preparation of AntOIR ( 8 ). Compound 2 was synthesized employing a previously reported . Iodination of 1 was carried out by diazotization of 2‐aminoanthracene through treatment with NaNO 2 /HCl.…”

“…Compound 2 was synthesized employing ap reviously reported. [6] Iodination of 1 was carried out by diazotization of 2-aminoanthracene through treatment with NaNO 2 /HCl. The correspondingd iazonium salt was reacted with KI to afford compound 2.S ubsequent treatment of compound 2 with ethynyltrimethylsilane under typical Sonogashira crosscoupling conditions produced compound 3.T hen, the deprotection reaction of 3 to obtain 4 was carried out with K 2 CO 3 in aM eOH/Et 2 O5 0:50 v/v solvent mixture.…”

Cofacial tris-porphyrins with anthracenic spacer

“…1-ethynyl-8-ethylsilylethynyl-anthracene (4) is prepared from the commercially available 1,8-dichloroanthraquinone in three steps. The starting product is first reduced by zinc powder to obtain the resulting 1,8-dichloroanthracene [13]. The latter product is then reacted with triethylsilylacethylene magnesium bromide in THF in the presence of PPH 3 and Ni(acac) 2 under reflux for three days [14].…”