Reaction #1248806

Reaction equation

Phenyl ethyl norbornene

dichloromethane

toluene

PENB

1-hexene

→

Hexyl Norbornene Phenethyl Norbornene

Solvents

—

THF poly(styrene)

mesitylene

Conditions

Workup

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturethe resulting mixture was maintained at 120° C. for 1 hour
3. 3
   TemperatureAfter cooling to room temperature
4. 4
   Otherthe copolymer was precipitated
5. 5
   workup.ADDITIONby adding methanol
6. 6
   FiltrationThe solid copolymer was collected by filtration
7. 7
   Otherdried at 80° C. in a vacuum oven
8. 8
   workup.DISSOLUTIONThe solid polymer was dissolved in an appropriate amount of mesitylene
9. 9
   Otherto give 10 wt % solid copolymer solution
10. 10
    OtherAfter drying
11. 11
    Other8.0 g was obtained (80%)
12. 12
    Otherto result in a 10 wt % copolymer solution

Procedure

HxNB (2.78 g, 0.0156 mol), Phenyl ethyl norbornene (PENB, CAS 29415-09-6) (7.22 g, 0.036 mol), 1-hexene (2.18 g, 0.026 mol) and toluene (57.0 g) were combined in a 250 mL serum bottle and heated to 120° C. in an oil bath. To this solution were added Pd1446 (3.0E-3 g, 2.1E-6 mol) and DANFABA (6.7E-3 g, 8.4E-6 mol) in concentrated solutions of dichloromethane. After addition, the resulting mixture was maintained at 120° C. for 1 hour. After cooling to room temperature, the copolymer was precipitated by adding methanol drop wise into the reaction mixture. The solid copolymer was collected by filtration and dried at 80° C. in a vacuum oven. The solid polymer was dissolved in an appropriate amount of mesitylene to give 10 wt % solid copolymer solution After drying, 8.0 g was obtained (80%). The molecular weight of the polymer was determined by GPC methods in THF poly(styrene) standard) Mw=127,332; Mn=39,206. The composition of the polymer was determined by 1H-NMR: HxNB/PENB=22/78. The composition of the copolymer was determined by 1H-NMR to be 54/46 HxNB/diPhNB. The refractive indices of this polymer were measured by prism coupling method and determined to be 1.5601 in TE mode and 1.5585 in TM mode at a wavelength of 633 nm. The dried copolymer was dissolved in sufficient mesitylene to result in a 10 wt % copolymer solution.

Source