Spiropyran as a reusable chemosensor for selective colorimetric detection of aromatic thiols

Literature Information

Publication Date 2014-02-19
DOI 10.1039/C3CP55478C
Impact Factor 3.676
Authors

Yasuhiro Shiraishi, Kohei Yamamoto, Shigehiro Sumiya, Takayuki Hirai


View Original

Abstract

Design of optical molecular probes for selective detection of aromatic thiols has attracted much attention. Although several types of probes have been proposed, all of them exhibit colorimetric or fluorometric response via irreversible reaction with aromatic thiols and cannot be reused. Here we report that a spiropyran dye is the first example of a reusable chemosensor for aromatic thiols. A colorless spiropyran dye (1) dissolved in aqueous media containing aromatic thiols is selectively isomerized to the colored merocyanine form in the dark. In contrast, visible light irradiation of the merocyanine form promotes successful reversion to the colorless spirocyclic form. Kinetic absorption analysis and ab initio calculations of the transition states revealed that this colorimetric response in the dark is ascribed to the decrease in activation energy for isomerization via the nucleophilic interaction between the aromatic thiol and the olefinic carbon of the dye.

Related Literature

Synthesis of chiral γ-aminophosphonates through the organocatalytic hydrophosphonylation of azadienes with phosphites

Ji Zhou, Guo-Fang Jiang, Yong-Gui Zhou

2018-01-29 Research Article

DOI: 10.1039/C7QO01158J

Correction: Ni(ii)-Catalyzed enantioselective Mukaiyama–Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters

Lei Xie, Hongli Ma, Jiaqi Li, Xuan Yu, Zhaohai Qin, Bin Fu

2017-07-20 Correction

DOI: 10.1039/C7QO90032E

A one-pot synthetic approach for the construction of a thiazolo[3,2-a]benzimidazole-linked quinazoline scaffold via palladium-catalyzed reactions

Ali Keivanloo, Atena Soozani, Mohammad Bakherad, Amir Hossein Amin

2018-01-09 Research Article

DOI: 10.1039/C7QO00751E

Visible light-induced selective aerobic oxidative transposition of vinyl halides using a tetrahalogenoferrate(iii) complex catalyst

Sanliang Li, Bo Zhu, Richmond Lee, Baokun Qiao, Zhiyong Jiang

2017-10-11 Research Article

DOI: 10.1039/C7QO00798A

Copper(ii) catalyzed domino synthesis of quinoline derivatives from arylamines and alkynes

Huimin Dai, Chun-Xiao Li, Chao Yu, Zihao Wang, Hong Yan, Changsheng Lu

2017-07-04 Research Article

DOI: 10.1039/C7QO00333A

Visible-light photoredox catalyzed hydroacylation of electron-deficient alkenes: carboxylic anhydride as an acyl radical source

Shupeng Dong, Guibing Wu, Xiaoqian Yuan, Chuncheng Zou, Jinxing Ye

2017-08-02 Research Article

DOI: 10.1039/C7QO00453B

Total synthesis of strictamine: a tutorial for novel and efficient synthesis

Shiju Zhang, Sha-Hua Huang

2017-10-17 Highlight

DOI: 10.1039/C7QO00837F

Copper-catalyzed radical 1,2-cyclization of indoles with arylsulfonyl hydrazides: access to 2-thiolated 3H-pyrrolo[1,2-a]indoles

Jiawei Zhu, Song Sun, Minfang Xia, Ning Gu, Jiang Cheng

2017-07-31 Research Article

DOI: 10.1039/C7QO00478H

The phosphorescence properties of a series of diarylethene-containing platinum complexes: the effect of ligand photoisomerization

Zhi-Xiang Zhang, Wei Wei, Fu-Quan Bai, Shamsa Bibi, Hong-Xing Zhang

2017-07-28 Research Article

DOI: 10.1039/C7QO00476A

Pd-Catalyzed thiophene directed regioselective functionalization of arenes: a direct approach to multiply-substituted benzyl amines

Jundie Hu, Guobao Li, Zhi-Bin Huang, Jingyu Zhang, Da-Qing Shi, Yingsheng Zhao

2017-04-28 Research Article

DOI: 10.1039/C7QO00236J

You might also like

Compound Q&A

What precautions should be taken when handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3)?

When handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3), safety go...

40716-16-34-Methyl-6-(trifluor...
Compound Q&A

What is 4-(3,5-Difluorophenyl)aniline (CAS: 405058-00-6)?

4-(3,5-Difluorophenyl)aniline is an aromatic organic compound with the CAS numbe...

405058-00-64-(3,5-Difluoropheny...
Compound Q&A

How is 5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid (CAS: 338982-07-3) typically synthesized?

5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid can ...

338982-07-35-{[4-(Trifluorometh...
Compound Q&A

What is the market or research trend for 4-Benzylaniline hydrochloride (CAS: 6317-57-3)?

The market for 4-Benzylaniline hydrochloride (CAS: 6317-57-3) is steadily growin...

6317-57-34-Benzylaniline hydr...
Compound Q&A

Is [3-(Diethylsulfamoyl)phenyl]boronic acid (CAS: 871329-58-7) safe?

[3-(Diethylsulfamoyl)phenyl]boronic acid is generally considered safe when handl...

871329-58-7[3-(Diethylsulfamoyl...
Compound Q&A

What are the main uses of 3-Bromo-2,5-dimethoxyaniline (CAS: 115929-62-9)?

3-Bromo-2,5-dimethoxyaniline is mainly used in the pharmaceutical and chemical i...

115929-62-93-Bromo-2,5-dimethox...
Compound Q&A

What regulatory guidelines apply to N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7)?

N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7) is subject to ...

915922-67-7N-Methyl-1-(5-methyl...
Compound Q&A

What industries use Carbamic acid, N-[(5S)-5,6-diamino-6-oxohexyl]-, 1,1-dimethylethyl ester (CAS: 24828-96-4)?

This compound is primarily used in the pharmaceutical industry for the synthesis...

24828-96-4Carbamic acid, N-[(5...
Compound Q&A

How should 2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) be stored?

2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) sho...

1298101-47-92-Methyl-2-propanyl ...
Compound Q&A

What industries use Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9)?

Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9) is utilized in the pharma...

367-33-9Ethyl 2-bromo-4,4,4-...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.