| 학회 | 한국고분자학회 |
| 학술대회 | 2005년 봄 (04/14 ~ 04/15, 전경련회관) |
| 권호 | 30권 1호, p.679 |
| 발표분야 | 분자전자 부문위원회 |
| 제목 | Design, Synthesis, and Properties of Nonlinear Optical Chromophores Containing Dialkoxy-Substituted Phenylenevinylene for Electro-Optics |
| 초록 | We have synthesized and characterized novel nonlinear optical chromophores containing dialkoxy-substituted phenylenevinylene for electro-optics. A Williamson etherification of methylhydroquinone with 2-ethylhexylbromide gave 1,4-bis-(2-ethyl-hexyloxy)-2-methyl-benzene, 1, in 66 % yield. Subsequent bromination using N-bromosuccinimide (NBS) and 2,2’-azobis(2-methylpropionitrile) (AIBN) in refluxing carbon tetrachloride produced 1-bromo-4-bromomethyl-2,5-bis-(2-ethyl-hexyloxy)-benzene, 2, in 51 % yield. Phosphonate 3 was obtained from 2 by a Michalis-Arbuzov reaction. The Wittig-Horner coupling of 3 with 4-diethylamino-benzaldehyde gave compound 4 in 84% yield. The terminal bromide of the compound 4 was transformed to aldehyde by treatment with n-butillithium and DMF according to the Bouveault method. The resulting compound 5 was reacted with 2-(3-cano-4, 5, 5-trimethyl-5H-furan-2-ylidene)-malononitrile to give a NLO chromophore, 2-(3-cyano-4-{2-[4-[2-(4-diethylamino-phenyl)-vinyl]-2,5-bis-(2-ethyl-hexyloxy)-phenyl]-vinyl}-5,5-dimethyl-5H-furan-2-ylidene)-malononitrile (St-TCF) in 56 % yield. The chemical structure and purity of the NLO chromophore were verified by 1H-NMR, 13C-NMR, DEPT spectra, and Mass spectrum. TGA showed that there was no weight loss of St-TCF upto 210 oC. St-TCF exhibited an absorption maximum at 636 nm in the chloroform solution from the UV/Vis absorption spectroscopy. We prepared films by spin-coating a solution of St-TCF and amorphous polycarbonate (APC, Aldrich Co.) in cyclopentanone. We obtained optical quality films doped with different NLO dye concentration (20-60 wt %). The films were poled using a contact poling method at a poling temperature under dc electric field 100 V/μm. The poling temperature was selected according to the glass transition temperature from the DSC measurement. The electro-optic coefficient, r33, was obtained by a simple reflection technique using a laser light of 1.55 μm. The films showed the electro-optic coefficient of 40-60 pm/V. 참고문헌 1.M. Lee, H.E. Katz, C. Erben, D.M. Gill, P. Gopalan, J.D. Heber, and D.J. McgGee, Science, 298, 1401 (2002). 2. Y. Shi, C. Zhang, H. Zhang, J.H. Bechtel, L.R. Dalton, B.H. Robinson, and W.H. Steier, Science 288, 119 (2002). 3. L.R. Dalton, J. Phys.: Condens. Matter 15, R897 (2003). 4. H. Ma and A.K.-Y. Jen, Adv. Mater. 13, 1201 (2001). 5. Y.V. Pereverzev, O.V. Prezhdo, and L.R. Dalton, Chem. Phys. Lett. 373, 207 (2003). 6. C.C. Tang and H.T. Man, Appl. Phys. Lett., 56, 1734 (1990). |
| 저자 | 김동욱, 윤은영, 이재왕, 윤성철, 임종선, 이창진 |
| 소속 | 한국화학(연) |
| 키워드 | Nonlinear Optical chromophores; Dialkoxy-substituted phenylenevinylene; Electro-optics |
