2-phenylsulfanylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In FIG. 4, the synthesis scheme for PAG 16 is carried out as follows: A brominated acetylthiophene derivative, 1-(5-bromothiophen-2-yl)ethanone (14) is reacted with 4-(phenylthio)benzaldehyde (1) in the presence of methanol and potassium hydroxide at room temperature to form a precursor compound, (E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one (15). The precursor compound (15) is exposed to microwave heating at 125° C. in the presence of diphenyliodonium hexafluoro phosphate (V) (6) to form a photoacid generator, (E)-(4-(3-(5-bromothiophen-2-yl)-3-oxoprop-1-enyl)phenyl)diphenylsulfonium hexafluorophosphate(V), identified herein as PAG 16. The reactions are carried out by conventional heating (Δ) and microwave heating (MW) and the Quantum yield per molecule of PAG 16 is 71% for conventional heating (Δ) and 83% for microwave heating (MW). In FIG. 4, the synthesis scheme for PAG 16

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In FIG. 4, the synthesis scheme for PAG 16 is carried out as follows: A brominated acetylthiophene derivative, 1-(5-bromothiophen-2-yl)ethanone (14) is reacted with 4-(phenylthio)benzaldehyde (1) in the presence of methanol and potassium hydroxide at room temperature to form a precursor compound, (E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one (15). The precursor compound (15) is exposed to microwave heating at 125° C. in the presence of diphenyliodonium hexafluoro phosphate (V) (6) to form a photoacid generator, (E)-(4-(3-(5-bromothiophen-2-yl)-3-oxoprop-1-enyl)phenyl)diphenylsulfonium hexafluorophosphate(V), identified herein as PAG 16. The reactions are carried out by conventional heating (Δ) and microwave heating (MW) and the Quantum yield per molecule of PAG 16 is 71% for conventional heating (Δ) and 83% for microwave heating (MW). In FIG. 4, the synthesis scheme for PAG 16

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl triphenylphosphonium iodide (1.57 g, 3.88 mmol) was dissolved in 25 mL ether in a 50 mL round-bottomed flask under dry nitrogen. To the mixture was added in one portion at 0° C. potassium tert-butoxide (0.47 g, 4.19 mmol) and it was stirred for 10 min at room temperature. 2-(phenylsulfanyl)benzenecarbaldehyde (2.77 mmol) was added in one portion at 0° C. and the reaction mixture was stirred until complete disappearance of the reactants (17 hr) at room temperature (followed by TLC). The mixture was added, to 50 mL of saturated sodium bicarbonate solution, followed by extraction with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using petroleum ether 60-80 as eluent. Yield: 0.53 g, 91%, colorless oil. 1H NMR (200 MHz, CDCl3): δ 5.33 (dd, J1=10.9, J2=1.2, 1H), 5.74 (dd, J1=17.4, J2=1.2, 1H), 7.16-7.65 (m, 10H) ppm. the reaction mixture was stirred until complete disappearance of the reactants (17 hr) at room temperature (followed by TLC) followed by extraction with 3×50 mL portions of ether The extracts were dried with magnesium sulfate evaporated The crude product was further purified by chromatography on silica gel

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-fluoro-benzaldehyde (2.00 g, 16.1 mmol), potassium carbonate (2.45 g, 17.7 mmol) and thiophenol (17.1 mmol) were dissolved in 10.0 mL DMF in a 50 mL round-bottomed flask under dry nitrogen, topped with a reflux condenser. The reaction mixture was heated to 80° C. for 24 hrs. After cooling, the mixture was added to 50 mL of saturated potassium carbonate solution and extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using 9:1 petroleum ether 60-80 and dichloromethane as eluent to give a yellow oil (2.46 g, 71%). 1H NMR (200 MHz, CDCl3): δ 7.07 (dd, J1=7.8, J2=1.2, 1H), 7.27-7.45 (m, 7H), 7.87 (dd, J1=7.3, J2=2.0, 1H), 10.37 (s, 1H) ppm. topped with a reflux condenser After cooling extracted with 3×50 mL portions of ether The extracts were dried with magnesium sulfate evaporated The crude product was further purified by chromatography on silica gel using 9:1 petroleum ether 60-80 and dichloromethane as eluent

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-fluorobenzaldehyde (0.443 mL) in 1,3-dimethyl-2-imidazolidinone (6.4 mL) was added potassium carbonate (0.659 g). Then benzenethiol (0.326 mL) was added, and the resulting mixture was stirred at 120° C. for 2.5 hours. The reaction mixture was cooled to room temperature and then partitioned between diethyl ether (60 mL) and water (15 mL). The organic layer was washed successively with water (15 mL×2) and brine (15 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.826 g). The reaction mixture was cooled to room temperature partitioned between diethyl ether (60 mL) and water (15 mL) The organic layer was washed successively with water (15 mL×2) and brine (15 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In FIG. 4, the synthesis scheme for PAG 16 is carried out as follows: A brominated acetylthiophene derivative, 1-(5-bromothiophen-2-yl)ethanone (14) is reacted with 4-(phenylthio)benzaldehyde (1) in the presence of methanol and potassium hydroxide at room temperature to form a precursor compound, (E)-1-(5-bromothiophen-2-yl)-3-(4-(phenylthio)phenyl)prop-2-en-1-one (15). The precursor compound (15) is exposed to microwave heating at 125° C. in the presence of diphenyliodonium hexafluoro phosphate (V) (6) to form a photoacid generator, (E)-(4-(3-(5-bromothiophen-2-yl)-3-oxoprop-1-enyl)phenyl)diphenylsulfonium hexafluorophosphate(V), identified herein as PAG 16. The reactions are carried out by conventional heating (Δ) and microwave heating (MW) and the Quantum yield per molecule of PAG 16 is 71% for conventional heating (Δ) and 83% for microwave heating (MW). In FIG. 4, the synthesis scheme for PAG 16