The Journal of Organic Chemistry· 2026Q2
Synthesis, Photophysical Properties, and Ab Initio Calculations of 2-(2-Hydroxy/methoxyphenyl)pyrimidines Substituted by Sterically Hindered Electron-Donating Groups
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- 2026year
Short summary
Methoxy-substituted pyrimidines with bulky electron-donating groups exhibit tunable fluorescence, with NPh2 derivatives showing the highest quantum yields, driven by steric effects and twisted geometries that balance charge transfer and proton transfer pathways.
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Key points
- Synthesized 2-(2-hydroxyphenyl)pyrimidine derivatives with DMAC, PXZ, PTZ, and NPh2 electron-donating groups and their methoxy precursors.
- Hydroxy derivatives were nonemissive due to efficient nonradiative deactivation via excited-state intramolecular proton transfer (ESIPT).
- Methoxy analogues displayed fluorescence and positive solvatochromism, indicative of intramolecular charge transfer (ICT).
- NPh2 substituted derivatives exhibited the highest fluorescence quantum yields.
- Theoretical calculations showed steric effects and twisted geometries control the balance between ICT, ESIPT, and radiative pathways.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract A series of 2-(2-hydroxyphenyl)pyrimidines bearing sterically hindered electron-donating groups (DMAC, PXZ, PTZ, and NPh2), together with their methoxy precursors, were synthesized and investigated by photophysical studies and ab initio calculations. While the hydroxy derivatives were essentially nonemissive due to efficient nonradiative deactivation associated with excited-state intramolecular proton transfer (ESIPT) processes, the methoxy analogues displayed clear fluorescence and positive solvatochromism, consistent with an intramolecular charge transfer (ICT) character. The emission properties strongly depended on the donor nature and substitution pattern, with NPh2 derivatives showing the highest fluorescence quantum yields. Theoretical calculations revealed that steric effects and twisted donor–acceptor geometries govern the balance between ICT, ESIPT, and radiative pathways. These results provide valuable insights for the design of pyrimidine-based color-tunable fluorophores.
The authors' abstract, as published at the source. The Journal of Organic Chemistry, 2026 · DOI ↗
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Field: Physical and Theoretical Chemistry
Physical and Theoretical ChemistryChemistry