A theoretical study of the photoinduced intramolecular proton transfer in 2-(2′-hydroxyphenyl)-imidazoline

A group of novel 2-aryl imidazole derivatives were synthesized and characterized by NMR spectra, X-ray, mass and CHN analysis. An excited state intramolecular proton transfer (ESIPT) process in hydroxy imidazoles (dmip and dmtip) have been studied using emission spectroscopy and it was detected that the two distinct ground state rotamers of I and II are responsible for the normal and the tautomer emission respectively. In hydrocarbon solvent, the tautomer emission predominates over the normal emission for both dmip and dmtip. This reveal that rotamer II is responsible for the tautomer emission and it is stabler than rotamer I which causes the normal emission. In alcoholic solvent like ethanol, a dramatic enhancement of normal emission is observed which was due to increased solvation, the more polar rotamer I become stabler than rotamer II. In dioxane-water mixtures it is observed that the addition of water inhibits the ESIPT process due to the formation of the intermolecular hydrogen bonding involving water. DFT calculations on energy, dipole moment, charge distribution of the rotamers in the ground and excited states of the imidazole derivatives were performed and discussed. PES calculation indicates that the energy barrier for the interconversion of two rotamers is too high in the excited state than the ground state.

show abstract

Synthesis, Structure, Luminescent and Intramolecular Proton Transfer in Some Imidazole Derivatives

Jayabharathi

Thanikachalam

Srinivasan

et al. 2010

J Fluoresc

View full text Add to dashboard Cite

show abstract

Application of reaction path concept in intramolecular proton transfer

Jaworski

1998

Computers & Chemistry

View full text Add to dashboard Cite

Nodal-plane model for excited-state intramolecular proton transfer of o-hydroxybenzaldehyde: substituent effect

Nagaoka

Nakamura

Nagashima

2002

Journal of Photochemistry and Photobiology A: Chemistry

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

A theoretical study of the photoinduced intramolecular proton transfer in 2-(2′-hydroxyphenyl)-imidazoline

Cited by 5 publications

References 29 publications

Synthesis, Structure, Luminescent and Intramolecular Proton Transfer in Some Imidazole Derivatives

Synthesis, Structure, Luminescent and Intramolecular Proton Transfer in Some Imidazole Derivatives

Application of reaction path concept in intramolecular proton transfer

Nodal-plane model for excited-state intramolecular proton transfer of o-hydroxybenzaldehyde: substituent effect

Contact Info

Product

Resources

About