Photoinduced Charge Migration in the Picosecond Regime for Thianthrene-Linked Acridinium Ions

Heteropolyacene with Thianthrenium Ring Systems ProvingπElectron Delocalization over S Atoms

“…The reaction mixture was then stirred at room temperature for 48 h. Pouring the resulting mixture into diethyl ether followed by collecting the white precipitate by filtration gave the desired product, methyl(1-methylthio-4-methylphenyl)(phenyl)sulfonium triflate, in 90% yield which was stored at 08C in the dark. 1 …”

“…The solution was refluxed for 2 h. Neutralization of the resulting mixture with HCl at 08C followed by extraction of the product with CHCl 3 , dehydration, rotary evaporation, and drying under vacuum afforded 1-methylthio-4-methylphenyl phenyl sulfide as an yellow liquid in 86% yield. 1 An aqueous solution of hydrogen peroxide (3.7 mL) and acetic acid (0.3 mL) was slowly added to a solution of 1-methylthio-4-methylphenyl phenyl sulfide (3.0 mmol, 0.78 g) in CH 2 Cl 2 (18 mL) and maintained at room temperature. The resulting mixture was stirred at room temperature for 10 h. After the reaction, extraction of the product with CHCl 3 followed by dehydration, rotary evaporation, and drying under vacuum afforded a crude product of 1a which contained a small amount of 1-methylsulfonyl-4-methylphenyl phenyl sulfide as a side product.…”

“…Purification was accomplished by column chromatography to give a pure product of 1a in 70% yield. 1 A solution of 1a (0.50 mmol, 0.13 g) in CH 2 Cl 2 (4 mL) with constant stirring in the dark was added very slowly to triflic acid (20 mL) maintained at room temperature. The resulting solution was stirred for 18 h in the dark.…”

“…After the reaction, pouring the resulting mixture into diethyl ether followed by collecting the white precipitate by filtration in the dark gave 2a in 78% yield as a gray powder. 1 …”

“…Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http:// www.tandfonline.com/page/terms-and-conditions INTRODUCTION The thianthrene ring system deserves much attention as a redox active center [1] and a spin coupler [2] due to the stability of the cation radical. [3] The unique reactivity of this cation radical is represented by its addition to a variety of alkenes providing monothianthrenium adducts.…”