Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms

Literature Information

Publication Date
DOI 10.1039/A902379H
Impact Factor 3.676
Authors


View Original

Abstract

Photochromic 1′,3′,3′-trimethyl-6,8-dinitro-spiro- [2H-1-benzopyran-2,2-indoline], (6,8-dinitro BIPS) has been studied in different solvents using 1H-NMR techniques, UV/visible spectroscopy, X-ray diffraction and electrospray ionisation mass spectroscopy (ESI-MS). Molar decadic absorption coefficients for 6,8-dinitro BIPS were found to range between 35000–45000 d mol-1 cm-1. 1H–1H NOESY and 1H-NMR experiments have established that in solution the merocyanine form of 6,8-dinitro BIPS is in rapid exchange between the trans-trans-cis (TTC) and trans-trans-trans (TTT) isomers. The 3B proton on the central bridging double bond of spiro-pyran merocyanines is labile in organic solvents. The closed form of 6,8-dinitro BIPS enantiomerises about the spiro C(2) carbon at a rate of 18 s-1 at 300 K. The activation energy for this process was estimated to be 46 kJ mol-1 using dynamic NMR.

Related Literature

Ex situ gas generation for lab scale organic synthesis

Joachim Demaerel, Cedrick Veryser, Wim M. De Borggraeve

2020-02-28 Review Article

DOI: 10.1039/C9RE00497A

Towards a sustainable electrochemical activation for recycling CO2: synthesis of bis-O-alkylcarbamates from aliphatic and benzyl diamines

Gianpiero Forte, Isabella Chiarotto, Frank Richter, Vinh Trieu, Marta Feroci

2017-08-29 Communication

DOI: 10.1039/C7RE00101K

Continuous nitration of alcohols in a Freon flow

Mikhail N. Zharkov, Svetlana S. Arabadzhi, Ilya V. Kuchurov, Sergei G. Zlotin

2019-04-12 Paper

DOI: 10.1039/C9RE00035F

Lignin valorization process control under feedstock uncertainty through a dynamic stochastic programming approach

Hanxi Bao, Zhiqiang Zhou, Georgios Kotsalis, Guanghui Lan, Zhaohui Tong

2019-07-17 Communication

DOI: 10.1039/C9RE00176J

Contents list

Front/Back Matter

DOI: 10.1039/D0RE90007A

Microfluidic synthesis of α-ketoesters via oxidative coupling of acetophenones with alcohols under metal-free conditions

Shiyu Guo, Zhongxue Dai, Jiawei Hua, Zhao Yang, Zheng Fang

2017-08-10 Paper

DOI: 10.1039/C7RE00107J

Contents list

Front/Back Matter

DOI: 10.1039/C7RE90021J

Scaling up of 3D printed and Ni/Al2O3 coated reactors for CO2 methanation

Lidia Protasova, Vesna Middelkoop, Nachiketa Ray, Michel Jouve, Alain Bengaouer

2019-06-10 Paper

DOI: 10.1039/C9RE00092E

Inside back cover

Cover

DOI: 10.1039/C9RE90034A

Design and 3D printing of a stainless steel reactor for continuous difluoromethylations using fluoroform

Tania Ciaglia, Eyke Slama, Matej Zadravec, Stefan Pfanner

2017-11-09 Paper

DOI: 10.1039/C7RE00176B

You might also like

Compound Q&A

What is 3-Fluoro-2-methylbenzylamine (CAS: 771573-36-5)?

3-Fluoro-2-methylbenzylamine is an organic compound with the CAS number 771573-3...

771573-36-53-Fluoro-2-methylben...
Compound Q&A

Is Tert-butyl 2-(oxetan-3-ylidene)acetate (CAS: 1207175-03-8) safe?

Tert-butyl 2-(oxetan-3-ylidene)acetate is considered safe for its intended uses ...

1207175-03-8Tert-butyl 2-(oxetan...
Compound Q&A

What precautions should be taken when handling 4-Acetyl-2-fluorobenzonitrile (CAS: 214760-18-6)?

Proper personal protective equipment (PPE) such as gloves, goggles, and a lab co...

214760-18-64-Acetyl-2-fluoroben...
Compound Q&A

How is 2-Ethyl-4-methyl-1,3-thiazole (CAS: 15679-12-6) typically synthesized?

2-Ethyl-4-methyl-1,3-thiazole is commonly synthesized via the reaction of thiour...

15679-12-62-Ethyl-4-methyl-1,3...
Compound Q&A

How should 5',5''-([2,2'-Bithiophene]-5,5'-diyl)bis(([1,1':3',1''-terphenyl]-4,4''-dicarboxylic acid)) (CAS: 1227780-71-3) be stored?

This compound should be stored in a cool, dry place away from direct sunlight an...

1227780-71-35',5''''-([2,2'-Bith...
Compound Q&A

What regulatory guidelines apply to L-Lysine Acetate Salt (CAS: 52315-92-1)?

L-Lysine Acetate Salt (CAS: 52315-92-1) is subject to various regulatory guideli...

52315-92-1L-LYSINE ACETATE SAL...
Compound Q&A

Is 6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) safe?

6-Fluoro-3-hydroxy-2-pyrazinecarboxamide (CAS: 259793-96-9) is generally conside...

259793-96-96-Fluoro-3-hydroxy-2...
Compound Q&A

What are the physical and chemical properties of 1,1'-Sulfonylbis(1H-imidazole) (CAS: 7189-69-7)?

1,1'-Sulfonylbis(1H-imidazole) is a crystalline solid with a molecular weight of...

7189-69-71,1'-Sulfonylbis(1H-...
Compound Q&A

What industries use 4-methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5)?

4-Methyl-7-nitro-1H-indole-3-carbonitrile (CAS: 289483-82-5) is primarily used i...

289483-82-54-methyl-7-nitro-1H-...
Compound Q&A

How should waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) be handled?

Waste containing 5-Bromo-3-indolyl-beta-galactoside (CAS: 97753-82-7) should be ...

97753-82-75-Bromo-3-indolyl-be...

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.