One-Pot Synthesis of Poly(2-Naphthyl Methacrylate)
Hamel M, et al. Polymer Bulletin, 2021, 78(5), 2805-2812.
Researchers have recently been interested in the possibility of creating fluorescent excimeres from poly(2-naphthyl methacrylate) (P2-NMA) and stabilizing the triplet state upon light irradiation. The one-pot preparation of poly(2-naphthyl methacrylate) from methacryloyl chloride and 2-naphthol and the polymerization of the in situ prepared monomers are described.
Synthesis of poly(2‑naphthyl methacrylate)
· In the dark, a round-bottom fask was charged with 2-naphthol (2.0 g, 13.88 mmol), and THF (25 mL) under argon atmosphere.
· Benzoyl peroxide (168 mg, 0.05 equiv., 0.693 mmol) and triethylamine (1.9 mL, 1.2 equiv., 16.65 mmol) were added at -10 °C. The solution was degassed by the classical freeze-thaw technique and subsequently heated to 0 °C.
· Methacryloyl chloride (1.38 mL, 1.0 equiv., 97% purity, 13.88 mmol) was added dropwise, and the mixture was allowed to reach room temperature. After completion of the reaction followed by TLC, the mixture was heated at 80 °C during 48 h.
· When the polymerization was completed, ammonium salts were discarded by fltration and the yellow solution was then reduced to ¼ of its volume and slowly poured into 100 mL of methanol. The polymer was fltered, dried and purifed with a Soxhlet apparatus during 3 days. A white powder (1.384 g) was fnally obtained.
Synthesis of 2-Naphthyl Methacrylate Copolymers and Their Dispersion Application
Yoshinaga K, et al. Colloid and Polymer Science, 2012, 290, 1221-1226.
The copolymer poly(MMA-co-NMA) was successfully prepared via free radical polymerization using 2-naphthyl methacrylate (NMA) and methyl methacrylate (MMA). These copolymers can be used to effectively disperse fullerene C60. In addition, the MMA/NMA block copolymers poly(MMA-b-NMA) can also effectively disperse C60.
· Synthesis of Poly(MMA-co-NMA)
A mixture of 2.0 mL (17.8 mmol) MMA, 0.50 mL (4.5 mmol) 2-naphthyl methacrylate (NMA) and 20 mg AIBN, and 3 mL dry THF was put into a 25-mL flask after purging with N2, and the solution was stirred at 75 °C for 7 h. The product was precipitated with diethyl ether, and filtration and successive drying under reduced pressure gave Poly(MMA-co-NMA).
· Synthesis of poly(MMA-b-NMA)
A mixture of 30 mg (0.009 mmol) 2, 0.80 mL (7.5 mmol) MMA, and 1.2 mL benzene was put into a test tube and the mixture was degassed by freezing and thawing under vacuum, followed by purging with nitrogen. The polymerization was carried out by irradiation of a high pressure Hg lump. Precipitation with diethyl ether gave 0.53 g poly(MMA-b-NMA) with Mn014,000 and Mw/Mn01.35.
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