Efficient Synthesis of Long-wavelength Absorbing Cyanochlorophyll a Derivatives via Stereoselective Horner-Wadsworth-Emmons Reaction

被引：4

作者：

Wu, Huiqiang ^{[1
]}

Wang, Xiangmin ^{[1
]}

Liu, Yang ^{[2
,3
]}

Zhao, Yu ^{[1
]}

Wang, Xinyue ^{[1
]}

Lee, Woo Kyoung ^{[2
,3
]}

Shim, Young Key ^{[2
,3
]}

Yoon, Il ^{[2
,3
]}

Xu, Xinming ^{[1
]}

Li, Jiazhu ^{[1
]}

机构：

[1] Yantai Univ, Coll Chem & Chem Engn, Yantai 264005, Peoples R China

[2] Inje Univ, Ctr Nano Mfg, Gimhae 50834, Gyeongnam, South Korea

[3] Inje Univ, Dept Nanosci & Engn, Gimhae 50834, Gyeongnam, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2020年 / 41卷 / 05期

基金：

中国国家自然科学基金; 新加坡国家研究基金会;

关键词：

Chlorophyll a; Chlorin; Cyanochlorin; Allomerization; Horner-Wadsworth-Emmons reaction; METHYL PYROPHEOPHORBIDE-A; CHLOROPHYLL DERIVATIVES; OPTICAL-PROPERTIES; ELECTRONIC-ABSORPTION; IN-VITRO; ALLOMERIZATION; CHLORINS; PYRIDYL; CONDENSATION;

D O I：

10.1002/bkcs.11998

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this article, we report the stereoselective Horner-Wadsworth-Emmons reaction of reactive carbonyl-substituted chlorophyll a derivatives with diethyl cyanomethylphosphonate. We found that the formyl or keto group at the chlorin periphery can react stereoselectively with phosphonate carbanions to produce a series of cyanomethylene-substituted chlorins with predominantly E geometry. Considering that no consistent records are available in the literature on the results of the allomerization of methyl pyropheophorbide a, we propose a reliable process for the transformation of this chlorophyll derivative. Our methodology represents a simple and efficient way for the preparation of novel, differently functionalized long-wavelength absorbing chlorins, those can be applied for photodynamic therapy, solar cells, and other relevant purposes.

引用

页码：504 / 512

页数：9

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