2026-10-12T03:53:07Z https://api.figshare.com/v2/oai

oai:figshare.com:article/33830037 2026-09-16T07:17:24Z category_1 category_4 category_146 category_915 category_873 category_45 category_46 category_133 portal_63 item_type_3 month_year_09_2026

Synthesis, Photophysical Properties, and Ab Initio Calculations of 2‑(2-Hydroxy/methoxyphenyl)pyrimidines Substituted by Sterically Hindered Electron-Donating Groups Clément Diguet (11772337) Angela Dellai (15412873) Adèle D. Laurent (1268595) Julien Massue (1819732) Françoise Robin-le Guen (24962031) Sébastien Gauthier (2345560) Sylvain Achelle (1763437) Biophysics Biochemistry Space Science Physical Sciences not elsewhere classified Chemical Sciences not elsewhere classified Sociology Immunology Plant Biology sterically hindered electron intramolecular charge transfer essentially nonemissive due ab initio </ 2 ‑( 2 2 -( 2 theoretical calculations revealed 2 </ sub tunable fluorophores substitution pattern steric effects radiative pathways pyrimidines substituted positive solvatochromism photophysical studies photophysical properties methoxy precursors donor nature donating groups derivatives showing based color 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 <i>ab initio</i> 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. 2026-09-16T00:00:00Z Dataset Dataset 10.1021/acs.joc.6c01185.s002 https://figshare.com/articles/dataset/Synthesis_Photophysical_Properties_and_Ab_Initio_Calculations_of_2_2-Hydroxy_methoxyphenyl_pyrimidines_Substituted_by_Sterically_Hindered_Electron-Donating_Groups/33830037 CC BY-NC 4.0