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In-situ NMR spectroscopic investigations of the organic photochromism in spiropyran and spiroxazine norbornens and their homopolymers

螺吡喃和螺恶嗪降冰片烯及其均聚物有机光致变色的原位核磁共振波谱研究

基本信息

批准号：
323314751
负责人：
Professorin Dr. Christina Marie Thiele
金额：
--
依托单位：
Arbeitskreis Thiele
依托单位国家：
德国
项目类别：
Research Grants
财政年份：
2016
资助国家：
德国
起止时间：
2015-12-31 至 2020-12-31
项目状态：
已结题

来源：
https://gepris.dfg.de/gepris/projekt/323314751?language=en
关键词：
situ NMR spectroscopic investigations organic

项目摘要

Upon irradiation with ultraviolet light (UV) spiropyranes and -oxazines show a change in color mostly from colorless to purple. This change in color is caused by a reversible ring opening reaction from the closed spiro- to the open merocyanine-form. The changes induced in physical properties, like the dipole moment, are used for the design of stimuli responsive materials. For the development of such materials, parameters like the degree of conversion to the open form upon irradiation or reaction rates of the thermal ring closing reaction are important. Furthermore these properties are related to the conditions present (solvent, temperature, etc.). The open merocyanine is stabilized by polar solvents, e.g., and thus thermal back reaction is slowed down. A goal of the proposed project is the investigation of the organic photochromism of monomeric and polymeric spiropyran and -oxazine-norbornenes with in-situ NMR spectroscopy. The use and development of NMR-spectroscopic methods to investigate organic photochromism is a main objective of the proposed project. Spiropyrans show degradation reactions upon irradiation. A deeper and systematic understanding of the pathways of photodegradation of spiropyran and spiroxazine norbornens is also in the focus of our investigations, as these limit the applicability of such systems. Furthermore the interaction of spiropyrans and -oxazine with (metal) ions is within the scope of this project as such interactions can have an influence on the photochromic behavior of spiropyrans and -oxazines. A deeper knowledge of the scope of these interactions would allow for a targeted use of ions to influence transport properties in mesoporous films. The monomers and polymers are synthesized in the the group of Andrieu-Brunsen and shall be used for the development of photocontrollable ionic transport in mesoporus silica-films. Results obtained from our in-situ NMR investigations of such spiropyrans and -oxazines with respect to photodecomposition reactions can then be used to improve before mentioned hybrid materials.

在用紫外光（UV）照射时，螺吡喃和-恶嗪显示颜色变化，主要从无色到紫色。这种颜色的变化是由从封闭的螺环到开放的部花青形式的可逆开环反应引起的。物理性质的变化，如偶极矩，用于设计刺激响应材料。对于这种材料的开发，参数如辐射时转化为开放形式的程度或热环闭合反应的反应速率是重要的。此外，这些性质与存在的条件（溶剂、温度等）有关。开放的汞通过极性溶剂稳定，从而减缓了热逆反应。该项目的一个目标是研究单体和聚合物螺吡喃和-恶嗪-单烯的有机光致变色与原位核磁共振光谱。利用和发展核磁共振光谱方法来研究有机光致变色是该项目的主要目标。螺吡喃在辐照后显示降解反应。一个更深入和系统的理解的光降解的螺吡喃和spiroxazine的pathways也是我们的调查的重点，因为这些限制了这种系统的适用性。此外，螺吡喃和-恶嗪与（金属）离子的相互作用也在本项目的范围内，因为这种相互作用会对螺吡喃和-恶嗪的光致变色行为产生影响。更深入地了解这些相互作用的范围将允许有针对性地使用离子来影响介孔膜中的传输特性。单体和聚合物在Andrieu-Brunsen的组中合成，并且将用于开发中孔二氧化硅膜中的光可控离子传输。从我们的原位NMR调查这样的螺吡喃和-恶嗪相对于光分解反应得到的结果，然后可以用来改善前面提到的混合材料。

项目成果

期刊论文数量（6）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Photoswitchable Intramolecular Hydrogen Bonds in 5-Phenylazopyrimidines Revealed By In Situ Irradiation NMR Spectroscopy.

原位辐照核磁共振波谱揭示 5-苯基氮杂嘧啶中的光可切换分子内氢键

DOI：
10.1002/chem.201705146
发表时间：
2018
期刊：
Chemistry
影响因子：
0
作者：
E. Procházková;L. Čechová;J. Kind;Z. Janeba;C. M. Thiele;M. Dračínský
通讯作者：
M. Dračínský

In situ Switching of Site-Selectivity with Light in the Acetylation of Sugars with Azo-Peptide Catalysts.

DOI：
10.1021/acs.joc.9b01913
发表时间：
2019-11
期刊：
The Journal of organic chemistry
影响因子：
0
作者：
Dominik Niedek;Frederik R. Erb;C. Topp;Alexander Seitz;R. Wende;A. Eckhardt;J. Kind;D. Herold;C. Thiele;P. Schreiner
通讯作者：
Dominik Niedek;Frederik R. Erb;C. Topp;Alexander Seitz;R. Wende;A. Eckhardt;J. Kind;D. Herold;C. Thiele;P. Schreiner

Photochromic dithienylethenes characterized by in situ irradiation NMR-spectroscopy and electrochemically induced responsiveness on gold substrates

通过原位辐照核磁共振波谱和金基底上的电化学诱导响应表征光致变色二噻吩乙烯