• 10.1142/s0218863505002761
  • Journal of Nonlinear Optical Physics & Materials
  • Volume 14
  • September 2005
  • pp 319-329

SYNTHESIS AND CHARACTERIZATION OF EFFICIENT TWO-PHOTON ABSORPTION CHROMOPHORES WITH INCREASED DIMENSIONALITY

Sub grignard for n-BuLi for nmr clean product

Details


Spirobifluorene: Synthesized spirobifluorene following the reported procedure (page 324-325) using  2-iodobiphenyl as starting material. It was difficult to isolate nmr-clean product and the yield was low, although they reported very high yield. Instead of n-BuLi, I used Grignard reagent made by reacting 2-iodobiphenyl with Mg-turnings in THF (reflux was needed) then reacted with 9-fluorenone to give 9-(2-biphenyl)-9-fluorenol. Acidic treatment gave easily isolated clean product of spirobifluorene with a good yield. Although I didn’t try but I believe 2 equivalent of t-BuLi would also work better than n-BuLi as t-BuLi can avoid dehydrohalogenation reaction to form by products.



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