Transformation of two-dimensional structures of noncyclic isobutenyl diamide compounds by tandem Claisen rearrangement

被引：14
|
作者：
Omori, Kazuhiro [1 ,2 ,3 ]
Kikkawa, Yoshihiro [1 ]
Tokuhisa, Hideo [1 ]
Kanesato, Masatoshi [1 ]
Hiratani, Kazuhisa [3 ]
机构：
[1] Natl Inst Adv Ind Sci & Technol, Photon Res Inst, Tsukuba, Ibaraki 3058562, Japan
[2] Ind Technol Ctr Tochigi Prefecture, Dept Mat Technol, Utsunomiya, Tochigi 3213224, Japan
[3] Utsunomiya Univ, Dept Appl Chem, Utsunomiya, Tochigi 3218585, Japan
来源：
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS | 2010年 / 356卷 / 1-3期
关键词：
Tandem Claisen rearrangement; Scanning tunneling microscopy; Two-dimensional structure; Self-assembly; Solid/liquid interface; Highly oriented pyrolytic graphite; SELF-ASSEMBLED MONOLAYERS; SOLID/LIQUID INTERFACE; DERIVATIVES; GRAPHITE; HOPG; AMIDECROWNOPHANES; COORDINATION; MACROCYCLES; CONVENIENT; COMPLEXES;
D O I：
10.1016/j.colsurfa.2009.12.038
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Two-dimensional structure of an isobutenyl diamide compound containing ether moieties was investigated by scanning tunneling microscopy at solid/liquid interface. The naphthalene units of the compound aligned in a wavy arrangement. The compound was modified by tandem Claisen rearrangement (TCR), which resulted in the transformation of the ether functions into hydroxyl group and in the formation of a C-C bond. Due to the alteration of the molecular structure, the two-dimensional structure changed from wavy to straight arrangements. In other words, drastic transformation of self-assembled structures could be achieved by the "simple" one-pot thermal reaction of TCR. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码：58 / 62
页数：5
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