Staudinger/Aza-Wittig 반응에 의한 삼발이 핵을 갖는 Frechet-type 덴드리머의 합성

한승철; 이재욱; 진성호; Seung Choul Han; Jae Wook Lee; Sung-Ho Jin

Polymer(Korea), Vol.38, No.3, 386-390, May, 2014

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Staudinger/Aza-Wittig 반응에 의한 삼발이 핵을 갖는 Frechet-type 덴드리머의 합성

Synthesis of Frechet-type Dendrimers with Tripodal Core via Staudinger/Aza-Wittig Reactions

한승철, 이재욱 ^†, 진성호^{1, †}

동아대학교 화학과
¹부산대학교 화학교육과

Seung Choul Han, Jae Wook Lee^†, and Sung-Ho Jin^{1, †}

Department of Chemistry, Dong-A University, Busan 604-714, Korea
¹Department of Chemistry Education, Pusan National University, Busan 609-735, Korea

E-mail:,

초록

덴드리머의 중심에 삼발이 핵을 갖는 덴드리머의 합성을 위한 효율적인 연결 방법이 개발되었다. 합성전략은 알데히드 덴드론과 아자이드기를 갖는 삼발이 핵 사이의 반응을 톨루엔 용매와 triphenylphosphine 존재하에서 진행하는 새로운 클릭화학(Staudinger/aza-Wittig 반응)을 이용하였다. 덴드리머의 삼발이 핵으로 작용할 수 있는 단위체인 1,3,5-tris-(3-azido-propoxy)-benzene을 합성하였고, 이 화합물의 아자이드기는 덴드리머의 형성에 이용되었다. 1,3,5-Tris-(3-azido-propoxy)-benzene을 이용하여 알데히드 덴드론과 Staudinger/aza-Wittig 반응을 통해 덴드리머를 합성하 였으며, 모든 덴드리머는 높은 수득률로 얻어졌다.

Efficient stitching methods for the synthesis of tripodal Frechet-type dendrimers containing secondary amine as a connector were elaborated. The synthetic strategy involved Staudinger/aza-Wittig reactions (new click reaction) between tripodal tris(azides) and aldehyde-dendrons in toluene in the presence of triphenylphosphine and followed by the reduction of imine intermediates. The tripodal core (1,3,5-tris-(3-azido-propoxy)-benzene) was chosen to serve as the azide functionalities for dendrimer growth. 1,3,5-Tris-(3-azido-propoxy)-benzene was stitched with the aldehyde-functionalized Frechet-type dendrons via Staudinger/aza-Wittig reactions leading to the formation of the corresponding Frechet-type dendrimers in high yields.

Keywords:Staudinger/aza-Wittig reaction;aldehyde;azide;dendrimer;tripodal.

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[4] Newkome GR, Moorefield CN, Vogtle F, Dendrimers and Dendrons: Concepts, Synthesis, Applications, Wiley-VCH, Weinheim (2001)

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