内消旋共轭尿嘧啶卟啉衍生物的阻转异构体及其组装结构。

Atropisomers of meso-conjugated uracyl porphyrin derivatives and their assembling structures.

作者信息

Arai Satoshi, Niwa Daisuke, Nishide Hiroyuki, Takeoka Shinji

机构信息

Department of Applied Chemistry, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan.

出版信息

Org Lett. 2007 Jan 4;9(1):17-20. doi: 10.1021/ol062394q.

DOI:10.1021/ol062394q

PMID:17192074

Abstract

[reaction: see text] We have synthesized a 5,15 meso-substituted methyluracyl porphyrin derivative bearing 6-methyluracyl units directly at the meso positions. The atropisomerization was regulated by steric replusion between the methyl substituents. When the atropisomers were mixed with alkylated melamine as a complementary hydrogen-bonding unit, the hydrogen-bonded assemblies were analyzed by diffusion-ordered spectroscopy (DOSY) in solution, which clarified that the alphabeta isomer formed a face-to-face dimer, whereas the alphabeta isomer took a zigzag structure.

摘要

[反应：见正文] 我们合成了一种5,15-中位取代的甲基尿嘧啶卟啉衍生物，其在中位直接带有6-甲基尿嘧啶单元。阻转异构化通过甲基取代基之间的空间排斥作用来调控。当将这些阻转异构体与作为互补氢键单元的烷基化三聚氰胺混合时，通过溶液中的扩散排序光谱法（DOSY）对氢键组装体进行了分析，结果表明αβ异构体形成了面对面的二聚体，而αβ异构体则呈锯齿形结构。