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Enantiospecific photochromic reaction of thiophenophan-1-enes

噻吩并-1-烯的对映特异性光致变色反应

基本信息

批准号：
16550126
负责人：
TAKESHITA Michinori
金额：
$ 2.37万
依托单位：
Saga University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2004
资助国家：
日本
起止时间：
2004 至 2005
项目状态：
已结题

项目摘要

Dithia-(dithienylethena)phane derivatives, composed of dithienylethene moieties and benzene bridges, were synthesized by a coupling reaction of the corresponding bis(chloromethyl)benzene with bis(mercaptomethyl)dithienylethene under high-dilution conditions. The products exhibit photochromic properties upon irradiation with ultraviolet and visible light. The photocyclization and cycloreversion quantum yields were determined, and a relationship between the photocyclization quantum yield and distance between the reactive carbon atoms of the phane derivatives established. The ortho isomer has a high efficiency in photocyclization due to its fixation in the photo-active anti conformation and short distance between the two reactive carbon atoms. The thermal stability of these photochromic compounds has been studied and the ortho isomer found to show thermal irreversibility.Photochromic [2.2]metacyclophan-1-ene in a PMMA (polymethylmethacryate) film reversibly changed the refractive index, which was estimated by ellipsometric analysis. For example, the refractive indexes of the open form and the photostationary state at 352 nm in PMMA films (10.6%) were 1.4934 and 1.4996 at 901.82nm, respectively, and the variation (Δn) was 0.0062. The calculated refractive indexes of the open and closed forms were 1.744 and 1.859, respectively. The refractive index of the PMMA film containing a photochromic dye changed photoreversibly due the photochromic reaction between the open and closed forms of [2.2]metacyclophan-1-ene.

以二(氯甲基)苯和二(硫代甲基)二硫乙烯为原料，在高稀释条件下，通过偶联反应合成了由二硫乙烯基团和苯桥组成的二硫杂环己烷衍生物。产品在紫外光和可见光照射下表现出光致变色性能。测定了光环化反应和环化反应的量子产率，建立了光环化反应量子产率与环烷类化合物活性碳原子间距之间的关系。邻位异构体由于固定在光活性的反构象中，两个活性碳原子之间的距离较短，具有较高的光环化效率。研究了这些光致变色化合物的热稳定性，发现邻位异构体表现出热不可逆性。在PMMA(聚甲基丙烯酸甲酯)薄膜中光致变色[2.2]偏环芳烃-1-烯可逆地改变了折射率，通过椭偏分析估算了折射率。例如，PMMA薄膜(10.6%)在901.82 nm处的光稳定态和开放态的折射率分别为1.4934和1.4996，变化量(Δn)为0.0062。开式和闭式的折射率分别为1.744和1.859。含有光致变色染料的PMMA薄膜的折射率发生了可逆的变化，这是由于[2.2]偏环芳烃-1-烯的开环和闭合的光致变色反应。

项目成果

期刊论文数量（26）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Reversible Optical Rotation Change According to the Enantiospecific Photochromic Reaction of [2. 2]Metacyclophan-lene

根据[2]的对映特异性光致变色反应可逆旋光变化。

DOI：
发表时间：
2004
期刊：
Chemistry Letters
影响因子：
1.6
作者：
M.K.Hossain;M.Takeshita;T.Yamato;M.Takeshita 他
通讯作者：
M.Takeshita 他

Photoreversible refractive index change of [2. 2]metacyclophan-l-ene in PMMA film

光可逆折射率变化[2．

DOI：
发表时间：
2006
期刊：
Optical Materials (印刷中)
影响因子：
0
作者：
Y.Yamaguchi;T.Tanaka;S.Kobayashi;T.Wakamiya;Y.Matsubara;Z.Yoshida.;M.Takeshita 他
通讯作者：
M.Takeshita 他

日本国特許

日本专利