Synthesis of photo-sensitive compounds containing cinnamate moieties for application on photo-alignment of liquid crystal 1 南台化材 Reporter : Chih-Hao Li(

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Synthesis of photo-sensitive compounds containing cinnamate moieties for application on photo-alignment of liquid crystal 1 南台化材 Reporter : Chih-Hao Li( 李志豪 ) Advisor : Ching-Dong Hsieh Date:

 Bisphenol A BPA  4,4’-Biphenol DOD  Cinnamoyl chloride  Triethylamine TEA  Ethyl acetate EAc 南台化材 2Experimental

3 Synthesis of BPA-Ci ＋ BPA(1.83g ， 8mmol) and TEA(2.43g ， 24mmol) were dissolved in EAc(25ml). Cinnamoyl chloride(4g ， 24mmol) was dissolved in EAc(15ml). Stirring was maintained for 24 h. Stirring was maintained for 24 h. Ice bath(0 ℃ ) The precipitate was filtered, washed with Na 2 CO 3 solution, and water. Finally, the solvent of the dried filtrate was evaporated under reduce pressure and dried under vacuum to give 45% of BPA-Ci.

南台化材 4 Synthesis of DOD-Ci ＋ dod(1.83g ， 8mmol) and TEA(2.43g ， 24mmol) were dissolved in EAc(25ml). Cinnamoyl chloride(4g ， 24mmol) was dissolved in EAc(15ml). Stirring was maintained for 24 h. Stirring was maintained for 24 h. Ice bath(0 ℃ ) The precipitate was filtered, washed with Na 2 CO 3 solution, and water. Finally, the solvent of the dried filtrate was evaporated under reduce pressure and dried under vacuum to give 60% of DOD-Ci.

1 H NMR spectra of the BPA-Ci Theoretical values=3:1:9:1 Actual values=3.01:0.98:9.05:1 a b d c b c cc d a b c d

1 H NMR spectra of the DOD-Ci Theoretical values=1:1:9 Actual values=0.98:1:9.01 a b c b c cc a b c a

7 (UV-vis) Fig. 1. The change of UV absorbance of compound solution with UV irradiation, (a)BPA-Ci, (b) DOD-Ci. (a)(b) DOD-Ci BPA-Ci 290nm

8 (UV-vis) Fig. 2. The change of UV absorbance of polymer solution with UV irradiation, (a)PCEMA, (b)PCEMA/DOD-Ci = 9/1. (a) (b) PCEMA 290nm

南台化材 9Conclusions 1. 1 H NMR showed that BPA-Ci and DOD-Ci was synthesized sucessfully and actual values of peak area was consistent of theoretical values. 2. The UV-vis spectra of cinnamate-containing monomer (BPA-Ci 、 DOD-Ci) and polymer PCEMA shows that C=C double bond disappears after UV irradiation for 30min. 3. The UV-vis spectra of PCEMA/DOD-Ci(9/1) blends shows that C=C double bond disappears after UV irradiation for 7min.

Future work 1.Observe the changes of UV absorbance of polymer solution with UV irradiation by UV-vis spectroscopy, (a)PCEMA/DOD-Ci = 7/3, 1/1, (b)PCEMA/BPA-Ci =9/1, 7/3, 1/1. 2. Observe the changes of UV absorbance of polymer films with UV irradiation by UV-vis spectroscopy, (a)PCEMA/DOD-Ci =9/1, 7/3, 1/1, (b)PCEMA/BPA-Ci =9/1, 7/3, 1/1.