• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

互变异构光开关:阴离子辅助的偶氮/嗪到腙的光致变色

Tautomeric photoswitches: anion-assisted azo/azine-to-hydrazone photochromism.

作者信息

Filo Juraj, Tisovský Pavol, Csicsai Klaudia, Donovalová Jana, Gáplovský Martin, Gáplovský Anton, Cigáň Marek

机构信息

Institute of Chemistry, Faculty of Natural Sciences, Comenius University Ilkovičova 6 SK-842 15 Bratislava Slovakia

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University Odbojárov 10 SK-832 32 Bratislava Slovakia.

出版信息

RSC Adv. 2019 May 21;9(28):15910-15916. doi: 10.1039/c9ra02906k. eCollection 2019 May 20.

DOI:10.1039/c9ra02906k
PMID:35521389
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9064339/
Abstract

The photoswitching properties of two easily synthesized isatin 4-nitrophenylhydrazones were investigated. Although the parent isatin 4-nitrophenylhydrazones exhibit low addressability which hampers their photochromic applications, the addition of strongly basic anions to phenylhydrazone solutions creates a new Vis-Vis photochromic system with the unusual azo/azine-to-hydrazone photo-tautomerization process as the photoswitching mechanism. To the best of our knowledge, this is the first report related to the anion-assisted azo/azine-to-hydrazone photo-tautomerism.

摘要

研究了两种易于合成的异吲哚酮4-硝基苯腙的光开关特性。尽管母体异吲哚酮4-硝基苯腙表现出较低的可寻址性,这阻碍了它们的光致变色应用,但向苯腙溶液中添加强碱性阴离子会产生一种新的可见-可见(Vis-Vis)光致变色体系,其光开关机制为不寻常的偶氮/嗪到腙的光互变异构过程。据我们所知,这是第一篇与阴离子辅助的偶氮/嗪到腙的光互变异构相关的报道。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/9c5d4fc3d136/c9ra02906k-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/2a1b29a85c8d/c9ra02906k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/e971890bf349/c9ra02906k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/6d665579508d/c9ra02906k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/1cdb78c4fddd/c9ra02906k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/d74304df98db/c9ra02906k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/029ebde92704/c9ra02906k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/2572832308aa/c9ra02906k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/f8b2b6d2b11a/c9ra02906k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/9c9ff9da1408/c9ra02906k-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/21930c8af7a3/c9ra02906k-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/9c5d4fc3d136/c9ra02906k-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/2a1b29a85c8d/c9ra02906k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/e971890bf349/c9ra02906k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/6d665579508d/c9ra02906k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/1cdb78c4fddd/c9ra02906k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/d74304df98db/c9ra02906k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/029ebde92704/c9ra02906k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/2572832308aa/c9ra02906k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/f8b2b6d2b11a/c9ra02906k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/9c9ff9da1408/c9ra02906k-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/21930c8af7a3/c9ra02906k-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6a55/9064339/9c5d4fc3d136/c9ra02906k-f7.jpg

相似文献

1
Tautomeric photoswitches: anion-assisted azo/azine-to-hydrazone photochromism.互变异构光开关:阴离子辅助的偶氮/嗪到腙的光致变色
RSC Adv. 2019 May 21;9(28):15910-15916. doi: 10.1039/c9ra02906k. eCollection 2019 May 20.
2
Isatin phenylhydrazones: anion enhanced photochromic behaviour.异吲哚酮苯腙:阴离子增强的光致变色行为。
Photochem Photobiol Sci. 2015 Nov;14(11):2064-73. doi: 10.1039/c5pp00275c.
3
Computational study on the prototropic tautomerism between simple oxo-, thio-, carbon-, aza-hydrazones, and their respective azines.简单的氧代、硫代、碳代、氮代腙及其相应的嗪之间质子转移互变异构的计算研究。
J Mol Model. 2022 Nov 18;28(12):393. doi: 10.1007/s00894-022-05387-2.
4
Azine-Hydrazone Tautomerism of Guanylhydrazones: Evidence for the Preference Toward the Azine Tautomer.胍腙的嗪-腙互变异构:倾向于嗪互变异构体的证据。
J Org Chem. 2016 Sep 2;81(17):7574-7583. doi: 10.1021/acs.joc.6b01258. Epub 2016 Aug 24.
5
Photoswitching hydrazones based on benzoylpyridine.基于苯甲酰吡啶的光致变色腙。
Phys Chem Chem Phys. 2019 Nov 28;21(44):24749-24757. doi: 10.1039/c9cp05049c. Epub 2019 Nov 4.
6
Spectroscopic and quantum chemical investigations of substituent effects on the azo-hydrazone tautomerism and acid-base properties of arylazo pyridone dyes.光谱和量子化学研究取代基对芳基偶氮吡啶酮染料的偶氮-腙互变异构和酸碱性质的影响。
Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 5;123:37-45. doi: 10.1016/j.saa.2013.12.064. Epub 2013 Dec 17.
7
Synthesis, structure and study of azo-hydrazone tautomeric equilibrium of 1,3-dimethyl-5-(arylazo)-6-amino-uracil derivatives.1,3-二甲基-5-(芳基偶氮)-6-氨基尿嘧啶衍生物的偶氮-腙互变异构平衡的合成、结构与研究
Spectrochim Acta A Mol Biomol Spectrosc. 2015 Apr 5;140:185-97. doi: 10.1016/j.saa.2014.12.027. Epub 2014 Dec 29.
8
Planarization-Induced Activation Wavelength Red-Shift and Thermal Half-Life Acceleration in Hydrazone Photoswitches.腙类光开关的平面化诱导激活波长红移和热半衰期加速。
ChemistryOpen. 2020 Feb 3;9(2):191-194. doi: 10.1002/open.201900340. eCollection 2020 Feb.
9
Computational exploration of the effect of molecular medium on the tautomerization of azo prodrug of 5-aminosalicylic acid.计算探索分子介质对 5-氨基水杨酸偶氮前药互变异构的影响。
J Mol Graph Model. 2019 Jan;86:160-169. doi: 10.1016/j.jmgm.2018.10.015. Epub 2018 Oct 19.
10
Path-Independent All-Visible Orthogonal Photoswitching for Applications in Multi-Photochromic Polymers and Molecular Computing.用于多光致变色聚合物和分子计算的与路径无关的全可见正交光开关
Angew Chem Int Ed Engl. 2024 Oct 24;63(44):e202409214. doi: 10.1002/anie.202409214. Epub 2024 Sep 17.

引用本文的文献

1
Azobenzene protonation as a tool for temperature sensing.偶氮苯质子化作为温度传感工具。
Beilstein J Org Chem. 2025 Jul 28;21:1528-1534. doi: 10.3762/bjoc.21.115. eCollection 2025.
2
Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative.一种腙衍生物的分子结构探索、密度泛函理论计算及抗氧化活性
Antioxidants (Basel). 2022 Oct 28;11(11):2138. doi: 10.3390/antiox11112138.
3
Effect of a =X-NH-Fragment, (X = C, N), on / Isomerization and ON/OFF Functionality of Isatin Arylhydrazones, ((Arylamino)Methylene)Indolin-2-Ones and Their Anions.

本文引用的文献

1
Shape-Persistent Actuators from Hydrazone Photoswitches.基于腙光开关的形状记忆致动器
J Am Chem Soc. 2019 Jan 23;141(3):1196-1200. doi: 10.1021/jacs.8b11558. Epub 2019 Jan 9.
2
Driving a Liquid Crystal Phase Transition Using a Photochromic Hydrazone.利用光致变色腙驱动液晶相变
J Am Chem Soc. 2018 Oct 24;140(42):13623-13627. doi: 10.1021/jacs.8b09622. Epub 2018 Oct 9.
3
Solution and Solid-State Emission Toggling of a Photochromic Hydrazone.一种光致变色腙的溶液态和固态发射切换
-NH-片段(X = C,N)对吲哚满二酮、(芳氨基)亚甲基)异吲哚啉-2-酮及其阴离子的异构化和 ON/OFF 功能的影响。
Molecules. 2020 Jul 6;25(13):3082. doi: 10.3390/molecules25133082.
J Am Chem Soc. 2018 Oct 3;140(39):12323-12327. doi: 10.1021/jacs.8b07108. Epub 2018 Sep 25.
4
Building Strain with Large Macrocycles and Using It To Tune the Thermal Half-Lives of Hydrazone Photochromes.构建含大尺寸大环的应变并利用其调控腙类光致变色化合物的热半衰期
J Am Chem Soc. 2018 Sep 19;140(37):11829-11835. doi: 10.1021/jacs.8b07612. Epub 2018 Sep 5.
5
New molecular switch architectures.新型分子开关结构。
Proc Natl Acad Sci U S A. 2018 Sep 18;115(38):9414-9422. doi: 10.1073/pnas.1714499115. Epub 2018 Jul 16.
6
Indigoid Photoswitches: Visible Light Responsive Molecular Tools.靛蓝类光开关:可见光响应分子工具
Acc Chem Res. 2018 May 15;51(5):1153-1163. doi: 10.1021/acs.accounts.7b00638. Epub 2018 Apr 25.
7
Molecular machines with bio-inspired mechanisms.具有生物启发机制的分子机器。
Proc Natl Acad Sci U S A. 2018 Sep 18;115(38):9397-9404. doi: 10.1073/pnas.1712788115. Epub 2018 Feb 26.
8
Tuning the Thermal Isomerization of Phenylazoindole Photoswitches from Days to Nanoseconds.调谐苯偶氮吲哚光开关的热互变异构反应:从天到纳秒。
J Am Chem Soc. 2018 Feb 28;140(8):2940-2946. doi: 10.1021/jacs.7b12871. Epub 2018 Feb 16.
9
Stereodivergent synthesis with a programmable molecular machine.具有可编程分子机器的立体发散性合成。
Nature. 2017 Sep 20;549(7672):374-378. doi: 10.1038/nature23677.
10
Hydrazone switches and things in between.腙开关及两者之间的物质。
Chem Commun (Camb). 2017 Jun 20;53(50):6674-6684. doi: 10.1039/c7cc02879b.