• 10.1021/j100014a003
  • The Journal of Physical Chemistry
  • Volume 99
  • April 1995
  • pp 4886-4893

Fluorescence Studies of Poly(p-phenyleneethynylene)s: The Effect of Anthracene Substitution

Reproducible Synthesis

Details


Swager et al reported the synthesis and fluorescence studies of poly(p-phenyleneethynylene)s. The experimental section, they made 4 different alkoxybenzenes using p-hydroquinone. I used this paper as a reference to synthesis a series of molecules: 1-((2-ethylhexyl)oxy)-4-ethynylbenzene, 1,4-bis((2-ethylhexyl)oxy)-2,5-diethynylbenzene, and 1,4-bis(dodecyloxy)-2,5-diethynylbenzene. The first step of this multiple synthetic route was the reflux p-hydroquinone with alkylbromide for 5 days. This step took more than a week including synthesis, purification, and crystallization. However, the final yield, ~75-80%, was reproducible for each reaction. The next step was the iodination. It was a very good choice, because iodine is a very good leaving group for the next step - Sonogashira coupling reaction. Sonogashira coupling reaction were carried out using either Pd(0)(PPh3)4 or Pd(II)(PPh3)2Cl2. Deprotection process carried out using either 20% KOH or K2CO3. Both bases efficiently deprotect, and able to isolate the pure product in a moderate yield. Since we used these monomers to make polymers, we ensured that they were very pure by recrystallization those several times.



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