反应详情

0.30 g (0.925 mmol) of 2,3,6,7,10,11-hexa-hydroxytriphenylene (3) was dissolved with 3 ml of DMF (dimethylformamide) in a 30 ml round-bottomed flask, and under stirring at room temperature, 0.27 g (6.75 mmol) of sodium hydride (60% in oil) was added little by little thereto. After the addition, the system was stirred for 10 minutes at room temperature and heated to ca. 80° C. on an oil bath, and 2.56 g (6.84 mmol) of 6-(perfluoroethyl)hexyl p-toluenesulfonate (2) dissolved in 2 ml of DMF was gradually added dropwise thereto. After the dropwise addition, the system was stirred for 5 hours under heating at the same temperature. After the reaction, the system was cooled to room temperature and stirred while adding chloroform and water thereto. The chloroform layer was condensed and purified by silica gel column chromatography with a chloroform eluent. After distilling off the chloroform, the resultant crystal was further purified by silica gel column chromatography with a toluene eluent and recrystallized from an acetone-methanol mixture solvent to obtain 0.52 g (yield=36.6%) of 2,3,6,7,10,1-hexakis[6-(perfluoro)hexyloxy]-triphenylene (1-5). The compound exhibited the following phase transition series.

1. additionAfter the addition
2. stirringthe system was stirred for 10 minutes at room temperature
3. temperatureheated to ca. 80° C. on an oil bath
4. additionwas gradually added dropwise
5. additionAfter the dropwise addition
6. stirringthe system was stirred for 5 hours
7. temperatureunder heating at the same temperature
8. customAfter the reaction
9. temperaturethe system was cooled to room temperature
10. stirringstirred
11. customcondensed
12. custompurified by silica gel column chromatography with a chloroform eluent
13. distillationAfter distilling off the chloroform
14. customthe resultant crystal was further purified by silica gel column chromatography with a toluene eluent
15. customrecrystallized from an acetone-methanol mixture solvent