A 1-Hydroxy-1H-imidazole ESIPT Emitter Demonstrating anti-Kasha Fluorescence and Direct Excitation of a Tautomeric Form

التفاصيل البيبلوغرافية
العنوان: A 1-Hydroxy-1H-imidazole ESIPT Emitter Demonstrating anti-Kasha Fluorescence and Direct Excitation of a Tautomeric Form
المؤلفون: Elena B. Nikolaenkova, Natalia V. Pervukhina, Katerina A. Vinogradova, Mark B. Bushuev, Alexey S. Berezin, Victor F. Plyusnin, Dmitry Yu. Naumov, Nikita A. Shekhovtsov, Alexsei Ya. Tikhonov
المصدر: ChemPlusChem. 86(10)
سنة النشر: 2021
مصطلحات موضوعية: symbols.namesake, Chemistry, Hydrogen bond, Intramolecular force, Stokes shift, symbols, Molecule, General Chemistry, Internal conversion (chemistry), Photochemistry, Ground state, Tautomer, Fluorescence
الوصف: The ability of 1-hydroxy-1H-imidazoles to exist in the form of two prototropic tautomers, the N-hydroxy and the N-oxide forms, can be utilized in the design of new types of ESIPT-fluorophores (ESIPT=excited state intramolecular proton transfer). Here we report the first example of 1-hydroxy-1H-imidazole-based ESIPT-fluorophores, 1-hydroxy-5-methyl-2,4-di(pyridin-2-yl)-1H-imidazole (HL), featuring a short intramolecular hydrogen bond O-H⋅⋅⋅N (O⋅⋅⋅N 2.56 A) as a pre-requisite for ESIPT. The emission of HL originates from the anti-Kasha S2 →S0 fluorescence in the N-oxide form as a result of a large S2 -S1 energy gap slowing down the S2 →S1 internal conversion. Due to an energy barrier between the N-hydroxy and N-oxide forms in the ground state, the HL molecules can be trapped and photoexcited in the N-oxide form leading to the Stokes shift of ca. 60 nm which is the smallest among known ESIPT-fluorophores.
تدمد: 2192-6506
URL الوصول: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c7d5e8f95be43a77418495b5f5dc02a9
https://pubmed.ncbi.nlm.nih.gov/34648233
Rights: CLOSED
رقم الانضمام: edsair.doi.dedup.....c7d5e8f95be43a77418495b5f5dc02a9
قاعدة البيانات: OpenAIRE