A Novel Class of π-Electron Dendrimers for Thermally and Morphologically Stable Amorphous Molecular Materials
✍ Scribed by Katsuhiko Katsuma; Yasuhiko Shirota
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 133 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0935-9648
No coin nor oath required. For personal study only.
✦ Synopsis
9H, methoxy), 6.42±6.45 (6H, Ph), 6.68±6.72 (6H, Ph), 7.02±7.05 (3H, core ar.), 7.16±7.51 (15H, naph.), 7.74±7.80 (6H, naph.).
1,3,5-Tris(2¢-anthracyl-4²-methoxyphenylamino)benzene 4e: In the first stage, 0.79 g (6 mmol) of phloroglucinol, 5 g (25 mmol) of 2-aminoanthracene, and 100 mg of iodine were heated together with 25 mL p-xylene for 16 h and the hot mixture was added to 100 mL ethanol with stirring. An or-ange±brown solid was separated on cooling, which was filtered, washed with methanol, and dried. It was redissolved in 10 mL cyclohexanone and reprecipitated out of ether and further purified by column chromatography using ethylacetate/hexane (1:3) as eluent to obtain 3.8 g (yield: 97.2 % ) of 1,3,5tris(2¢-anthracylamino)benzene 3a (C 48 H 33 N 3 /651.81). IR (n, cm ±1 ): 3372 (N±H); 2910±3050 (C±H ar.); 1609, 1519, 1461 (C=C); 1281 (C±N).
In the second stage, 1.3 g (2 mmol) of 3a, 4.6 g (20 mmol) of 4-iodoanisole, 1.4 g (24 mmol) of potassium hydroxide, and 1.2 g of copper powder were heated together in 15 mL of petroleum ether (b.p.: 170±180 C) under argon atmosphere at 170 C for 24 h. The reaction mixture was extracted while hot with 10 mL THF and the product was reprecipitated out of methanol and purified by column chromatography using ethylacetate/hexane (1:4) as eluent to obtain 1.5 g (yield: 77.3 %) of 4e (C 69 H 51 N 3 O 3 /970.18). IR (n, cm ±1 ): 2960±3047 (C±H ar.);