Titanium(IV) Chloride (ca. 19% in Toluene, ca. 1.0mol/L)

• Benzophenone [B0083]
• Titanium(IV) Chloride (ca. 19% in Toluene, ca. 1.0 mol/L) [T3238]
• Zinc (Powder) [Z0015]
• Tetrahydrofuran (= THF)

A suspension of　benzophenone (500 mg, 2.7 mmol) and zinc (540 mg, 8.2 mmol) in dried THF (30 mL) was stirred under nitrogen at 0 ℃. TiCl₄ (ca. 19% in toluene, ca. 1.0 mol/L) (5.5 mL, 5.5 mmol) was dropwised for 10 min. The ice bath was removed and the mixture was stirred at 70 ℃ for 30 min. The reaction was quenched with aqueous solution of potassium carbonate and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude product was washed with hexane to give tetraphenylethylene (1) as a white solid (314 mg, y. 69%).

The reaction mixture was monitored by TLC (hexane:dichloromethane = 4:1, Rf = 0.48).

Tetraphenylethylene (1)

¹H NMR (270 MHz, CDCl₃); δ 7.12-7.08 (m, 4H), 7.04-7.01 (m, 16H).

• Dissipative aggregation-induced emission behaviour of an amino-functionalized tetraphenylethene using a pH oscillator
• E. Liang, F. Su, Y. Liang, G. Wang, W. Xu, S. Li, C. Yang, J. Tang, N. Zhou, Chem. Commun. 2020, 56, 15169.