A new class of N–H excited-state intramolecular proton transfer (ESIPT) molecules bearing localized zwitterionic tautomers

Literature Information

Publication Date 2016-08-11
DOI 10.1039/C6CP05236C
Impact Factor 3.676
Authors

Anton J. Stasyuk, Yi-Ting Chen, Chi-Lin Chen, Pei-Jhen Wu, Pi-Tai Chou


View Original

Abstract

A series of new amino (NH)-type intramolecular hydrogen-bonding (H-bonding) compounds have been strategically designed and synthesized. These molecules comprise a 2-(imidazo[1,2-a]pyridin-2-yl)aniline moiety, in which one of the amino hydrogens was replaced with substituents of different electronic properties. This, together with the versatile capability for modifying the parent moiety, makes feasible comprehensive spectroscopy and dynamics studies of excited-state intramolecular proton transfer (ESIPT) as a function of N–H acidity. Different from other (NH)-type ESIPT systems where the ESIPT rate and exergonicity increase with an increase in the N–H acidity and hence the H-bonding strength, the results reveal an irregular relationship among ESIPT dynamics, thermodynamics and H-bond strength. This discrepancy may be rationalized by the localized zwitterionic nature of 2-(imidazo[1,2-a]pyridin-2-yl)aniline in the proton-transfer tautomer form, which is different from the π-delocalized tautomer form in other (NH)-type ESIPT systems.

Related Literature

Development of strong and high-barrier food packaging films from cyclic-anhydride modified bacterial cellulose

Zhuolun Jiang, Ka Man Cheung, To Ngai

2023-10-23 Paper

DOI: 10.1039/D3SU00219E

Optimization of Pavlova gyrans biomass production and the fatty acid profile using a two-step approach

Filipe Maciel, Hugo Pereira, Joana Silva

2023-09-25 Paper

DOI: 10.1039/D3FB00110E

In situ crosslinked Schiff base biohydrogels containing Carica papaya peel extract: application in the packaging of fresh berries

Ganeswar Dalei, Swagat Kumar Das, Susri Sangita Mohapatra

2023-09-13 Paper

DOI: 10.1039/D3FB00096F

Introducing RSC Applied Interfaces

2024-01-08 Editorial

DOI: 10.1039/D3LF90001K

Developing 3D computational models to capture the spatial, temporal and thermal behavior as laser beams propagate through photo-thermally responsive gels

Victor V. Yashin, Fariha Mahmood, Kalaichelvi Saravanamuttu, Anna C. Balazs

2023-11-16 Paper

DOI: 10.1039/D3LF00156C

Sustainability-driven photocatalysis: oxygen-doped g-C3N4 for organic contaminant degradation

Soumya Ranjan Mishra, Vishal Gadore, Md. Ahmaruzzaman

2023-12-04 Tutorial Review

DOI: 10.1039/D3SU00384A

Eco-design of the remembrance poppy: a life cycle assessment study

Andrea Paulillo, Martina Pucciarelli, Phil Prior, Paola Lettieri

2023-11-28 Paper

DOI: 10.1039/D3SU00279A

A comprehensive review on isochoric freezing: a recent technology for preservation of food and non-food items

Dhanya R., Abhirami Panoth, N. Venkatachalapathy

2023-10-12 Review Article

DOI: 10.1039/D3FB00146F

A metamaterial based sensor for moisture and density of cereal flours

Aswathi P. V., Anju Sebastian, Lulu Varghese, Joseph V. P., Jolly Andrews

2023-11-07 Paper

DOI: 10.1039/D3FB00126A

Storage stability assessment of guava fruit (Psidium guajava L.) cv. ‘Gola’ in response to different packaging materials

Ali Asad Yousaf, Kashif Sarfraz Abbasi, Muhammad Suhail Ibrahim, Asma Sohail, Mamoona Faiz, Mehwish Khadim

2023-11-28 Paper

DOI: 10.1039/D3FB00113J

You might also like

Compound Q&A

Is 2-(2-chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) safe?

2-(2-Chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) is generally consi...

7765-11-92-(2-chloroacetamido...
Compound Q&A

Is 2-(Benzyloxy)-5-bromobenzoic acid (CAS: 62176-31-2) safe?

2-(Benzyloxy)-5-bromobenzoic acid can be handled safely if appropriate precautio...

62176-31-22-(Benzyloxy)-5-brom...
Compound Q&A

What is (4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride (CAS: 1159825-48-5)?

(4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride is a chemical compound ...

1159825-48-5(4-Methyl-1,2,5-oxad...
Compound Q&A

What is 2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54-7)?

2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54...

917985-54-72-(5-Hexylthiophen-2...
Compound Q&A

Are there alternatives to 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS: 102771-26-6) in synthesis?

While 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS:...

102771-26-64-(8-Methyl-9H-1,3-d...
Compound Q&A

What is the market or research trend for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine-6-carboxylate (CAS: 851376-80-2)?

The market for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine...

851376-80-2tert-butyl 3-hydroxy...
Compound Q&A

How should waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) be handled?

Waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) should ...

6844-58-23,5-Diamino-1H-pyraz...
Compound Q&A

How is (6-Fluoro-3-pyridinyl)boronic acid (CAS: 351019-18-6) typically synthesized?

(6-Fluoro-3-pyridinyl)boronic acid can be synthesized through the reaction of 6-...

351019-18-6(6-Fluoro-3-pyridiny...
Compound Q&A

What industries use Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9)?

Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9) finds applications in vario...

10065-79-9Dibenzyl carbonimido...
Compound Q&A

What is the market or research trend for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4)?

The market for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4) is g...

74228-83-4(beta,beta,2,3,4,5,6...

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 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.