Work

8-(Pyridin-2-yl)quinolin-7-ol and Beyond: Theoretical Design of Tautomeric Molecular Switches with Pyridine as a Proton Crane Unit

Year: 2024

Type: article

Abstract: Long-range proton transfer in several conjugated proton cranes, originating from 7-hydroxy quinoline as a proton transfer platform, has been investigated theoretically by means of DFT and TD-DFT methodology. Major emphasis was given to their applicability to provide clean switching upon irradiation. The border conditions require the existence of a single enol tautomer in the ground state, which under excitation through a series of consecutive exited and ground state intramolecular proton transfer steps is transferred to the keto tautomer. It was shown that the most suitable candidates are based on using iso-quinoline, pyrimidine and 4-nitropyridine as proton crane units. Their suitability is a function of aromaticity changes, the basicity of the nitrogen atom from the proton crane unit and the structural effects originating from their conjugation with 7-hydroxy quinoline.

Source: Chemistry

DOI: 10.3390/chemistry6060097

Authors: Lidia Zaharieva, Daniela Nedeltcheva-Antonova, Liudmil Antonov

Institutions: Bulgarian Academy of Sciences, Institute of Electronics, Institute of Organic Chemistry with Centre of Phytochemistry

Language: English

Topic: Photochromic and Fluorescence Chemistry

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $2,046

Funder: Bulgarian National Science Fund