Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Synthesis and X-ray Structure Analysis of (Z)-1-(4-Bromophenyl)-1-phenyl-2-(4-tert-butylphenyl)ethene

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

  • Kim, Chul-Bae (School of Chemical Engineering and Materials Science, Chung-Ang University) ;
  • Cho, Hyun-Jong (School of Chemical Engineering and Materials Science, Chung-Ang University) ;
  • Lee, Sung-Kyung (School of Chemical Engineering and Materials Science, Chung-Ang University) ;
  • Park, Kwangyong (School of Chemical Engineering and Materials Science, Chung-Ang University)
  • 김철배 (중앙대학교 화학신소재공학부) ;
  • 조현종 (중앙대학교 화학신소재공학부) ;
  • 이성경 (중앙대학교 화학신소재공학부) ;
  • 박광용 (중앙대학교 화학신소재공학부)
  • Received : 2009.04.01
  • Accepted : 2009.04.27
  • Published : 2009.06.10
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Abstract

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 $56.5(4)^{\circ}$ and $74.1(4)^{\circ}$, respectively.

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 $56.5(4)^{\circ}$이며 브로모페닐 고리와 페닐 고리 간의 dihedral angle은 $74.1(4)^{\circ}$였다.

Keywords

Acknowledgement

Supported by : 중앙대학교

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