52212-90-5

Usage

InChI:InChI=1/C16H14O5S/c1-20-15-11-5-3-4-6-12(11)16(21-2)14-9-10(22(17,18)19)7-8-13(14)15/h3-9H,1-2H3,(H,17,18,19)/p-1

Upstream product

• 137308-86-2 Diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate 
• 121172-98-3 p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulphonate 

Relevant academic research and scientific papers

Photoinduced Intramolecular Electron Transfer Mechanism for Photochemical Dissociation of Para-Substituted Benzyl 9,10-Dimethoxyanthracene-2-sulfonates

The photochemical behavior of para-substituted benzyl 9,10-dimethoxyanthracene-2-sulfonates with varying electron-withdrawing ability of substituents has been investigated by both steady-state and laser flash photolysis techniques. p-Nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate is photochemically dissociated to give 9,10-dimethoxyanthracene-2-sulfonic acid, 9,10-dimethoxy-2-(p-nitrobenzyl)anthracene, and p,p'-dinitrobibenzyl which were assigned on the basis of mass spectroscopic data and 1H NMR spectroscopy.Quantum yields for the photodissociation of p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate and for the formation of 9,10-dimethoxyanthracene-2-sulfonic acid with excitation at 436 nm in degassed acetonitrile solution are 0.12 +/- 0.03 and 0.10 +/- 0.03, respectively.Photodissociation of p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate is considered to proceed via an intramolecular electron transfer from the excited singlet state of 9,10-dimethoxyanthracene moiety to p-nitrobenzyl moiety followed by the heterolytic bond cleavage at oxygen-carbon bond of the sulfonyl ester from the fact that the transient absorptions at 310 and 425 nm due to 9,10-dimethoxyanthracene-2-sulfonate radical cation and around 340 nm due to the p-nitrobenzyl radical anion are detected in laser spectroscopy.The rate constant for dissociation of p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulfonate was determined to be (1.1 +/- 0.5) * 105 s-1 by kinetic analyses.Possible mechanisms for the photodissociation are discussed and it is concluded that the three factors which control the rate of photodissociation are intramolecular electron transfer, feasibility of oxygen-carbon bond scission, and stability of benzyl-type radical formed by the photodissociation.

Intra-ion-pair Electron Transfer Mechanism for Photolysis of Diphenyliodonium Salt Sensitized by 9,10-Dimethoxyanthracene-2-sulfonate Counteranion

Diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate is photochemically dissociated to give 9,10-dimethoxyanthracene-2-sulfonic acid.The dissociation is considered to proceed via an intra-ion-pair electron transfer from 9,10-dimethoxyanthracene moiety to iodonium moiety.The counteranion acts as both spectral sensitizer for diphenyliodonium ion and precursor for photo-acid generator.

Photochemical Dissociation of p-Nitrobenzyl 9,10-Dimethoxyanthracene-2-sulphonate via Intramolecular Electron Transfer

While o-nitrobenzyl aromatic sulphonates are known to photodissociate via an intramolecular rearrangement, photodissociation of p-nitrobenzyl aromatic sulphonates has not been reported.In this study, we report that p-nitrobenzyl 9,10-dimethoxyanthracene-2-sulphonate is photochemically dissociated to give 9,10-dimethoxyanthracene-2-sulphonic acid, 9,10-dimethoxy-2-(p-nitrobenzyl)-anthracene, and p,p'-dinitrobibenzyl.The dissociation is considered to proceed via an intramolecular electron transfer from the 9,10-dimethoxyanthracene moiety to the p-nitrobenzyl moiety.The quantum yield of the photodissociation in acetonitrile is 0.11 and the spectral response extends to 450 nm.The quantum yield is much higher than those of o-nitrobenzyl esters.