Description
1, 6-dibromopyrene is a kind of pyrene chemical. It is majorly used
as organic intermediate, OLED (organic light-emitting diodes)
materials and photoelectric material. It, together with its 1, 8-
isomer, can be produced by the double bromination of pyrene with
bromine. It can be applied to the synthesis of bipyridine and
terpyridine based ruthenium metallosynthons.
Chemical Properties
white powder
Uses
1,6-Dibromopyrene is an important intermediate for the synthesis of perylene diimide (PDI) derivative host structures. Perylene diimide derivatives are one of several important classes of discotic liquid crystal molecules.
Synthesis
Specifically, pyrene (12.2g, 60 mmol) and 300 ml carbon tetrachloride are placed into a three-necked flask with a dropping funnel. Under room temperature, stirring, and nitrogen protection, bromine (11.5ml, 0.23mol) is dissolved in 50ml carbon tetrachloride, and then the solution is added to the reactor (the molar ratio of pyrene to bromine is 1:3.83). The mixed reaction solution is stirred at room temperature for 59 hours, then filtered, and the crude product is washed three times with 100ml methanol. The crude product is recrystallized with a mixed solvent of 260ml carbon tetrachloride and tetrahydrofuran to obtain 19.77g of pure 1,6-dibromopyrene, with a yield of 90.9% and a purity of 99.8%.
References
Goze, Christine, et al. "Synthesis of bipyridine and terpyridine based ruthenium metallosynthons for grafting of multiple pyrene auxiliaries."Tetrahedron letters 44.48 (2003): 8713-8716.
Kaplunov, Mikhail G., et al. "Novel 1, 8-bis(diarylamino)pyrenes as OLED materials." Mendeleev Communications 26.5(2016):437-439.
Gong, Xiaojie, et al. "Two Symmetrically Bis‐substituted Pyrene Derivatives: Synthesis, Photoluminescence, and Electroluminescence." Chinese Journal of Chemistry 33.8 (2015): 967-973.
