(Z)-1-(4-브로모페닐)-1-페닐-2-(4-tert-부틸페닐)에텐의 합성 및 X-선 구조분석

김철배; 조현종; 이성경; 박광용; Chul-Bae Kim; Hyun-Jong Cho; Sung-Kyung Lee; Kwangyong Park

Journal of the Korean Industrial and Engineering Chemistry, Vol.20, No.3, 335-338, June, 2009

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(Z)-1-(4-브로모페닐)-1-페닐-2-(4-tert-부틸페닐)에텐의 합성 및 X-선 구조분석

Synthesis and X-ray Structure Analysis of (Z)-1-(4-Bromophenyl)-1-phenyl-2-(4-tert-butylphenyl)ethene

김철배, 조현종, 이성경, 박광용 ^†

중앙대학교 화학신소재공학부

Chul-Bae Kim, Hyun-Jong Cho, Sung-Kyung Lee, and Kwangyong Park^†

School of Chemical Engineering and Materials Science, Chung-Ang University, Seoul 156-756, Korea

E-mail:

초록

유기발광다이오드의 청색 발광 물질로 많은 관심을 받고 있는 디스티릴아릴렌 화합물들의 합성 과정에서 핵심적인 중간체인 브로모트리페닐에틸렌 화합물들은 브로모벤조페논과 벤질포스포네이트의 반응을 통하여 얻어진다. 이 반응은 분리하기 어려운 (Z)-와 (E)-기하이성질체가 60 : 40의 비율로 생성한다. 본 연구에서는 2-프로탄올을 이용한 재결정법을 통하여 (Z)-이성질체를 간단하게 분리하였다. X-ray를 이용하여 (Z)-이성질체의 결정 구조를 살펴본 결과, tert-부틸페닐 고리와 브로모페닐 고리 간의 dihedral angle은 56.5(4)°이며 브로모페닐 고리와 페닐 고리 간의 dihedral angle은 74.1(4)°였다.

As important intermediates for blue emitting materials of organic light-emitting diodes, bromotriphenylethylene derivatives for distrylarylenes are prepared by reactions of bromobenzophenone with benzylphosphonates. The reaction produces a 60 : 40 mixture of (Z)- and (E)-geometric isomers that are difficult to be resolved. The (Z)-isomer is successfully isolated by a selective recrystallization process using 2-propanol as a solvent. The X-ray structure analysis of (Z)-isomer shows that dihedral angles between tert-butylphenyl ring and bromophenyl ring and between bromophenyl ring and phenyl ring are 56.5(4)° and 74.1(4)°, respectively.

Keywords:single crystal;X-ray structure analysis;triphenylethene;Horner-Wadsworth-Emmons

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Kim CB, Cho CH, Chai KY, Park K, Acta. Cryst., E64, o457 (2008)

[Related Articles]

[1] Li YX, Tao XT, Wang FJ, He T, Zhang LL, Jiang MH, Chem. Phys. Lett., 470, 264 (2009)

[2] Shih PI, Shua CF, Appl. Phys. Lett., 88, 251110 (2006)

[3] Su HJ, Wu FI, Tseng YH, Shu CF, Adv. Funct. Mater., 15(7), 1209 (2005)

[4] Hosokawa C, Higashi H, Nakamura H, Kusumoto T, Appl. Phys. Lett., 67, 3853 (1995)

[5] Wen SW, Lee MT, Chen CH, IEEE J. Display Tech., 1, 90 (2005)

[6] Hung LS, Chen CH, Mater. Sci. Eng. R-Rev. J., 39, 143 (2002)

[7] Williams RT, Hodge P, Yeates S, React. Funct. Polym., 67, 1061 (2007)

[8] Williams RT, Hodge P, Yeates S, Polym. Adv. Technol., 19, 569 (2008)

[9] Sakanoue T, Yahiro M, Adachi C, Burroughes JH, Oku Y, Shimoji N, Takahashi T, Toshimitsu A, Appl. Phys. Lett., 92, 053505 (2008)

[10] Sakanoue T, Yahiro M, Adachi C, Uchiuzou H, Takahashi T, Toshimitsu A, Appl. Phys. Lett., 90, 171118 (2007)

[11] Wadsworth WW, Emmons WD, J. Am. Chem. Soc., 83, 1733 (1961)

[12] Chen Y, Lai SP, J. Polym. Sci. A: Polym. Chem., 39(15), 2571 (2001)

[13] Cho C, Park K, Bull. Korean. Chem. Soc., 28, 1159 (2007)

[14] Schmidt C, Chishti NH, Breining T, Synthesis, 391 (1982)

[15] Bruker. SMART and SAINT. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.

[16] Farrugia LJ, J. Appl. Cryst., 30, 565 (1997)

[17] Gao L, Peng H, He HW, Acta. Cryst., E62, o5032 (2008)

[18] Ogawa K, Sabo T, Yoshimura S, Takeuchi Y, Toriumio K, J. Am. Chem. Soc., 114, 1041 (1992)

[19] Kim CB, Cho CH, Chai KY, Park K, Acta. Cryst., E64, o457 (2008)