دورية أكاديمية
ESIPT-based benzazole-pyromellitic diimide derivatives. A thermal, electrochemical, and photochemical investigation.
| العنوان: | ESIPT-based benzazole-pyromellitic diimide derivatives. A thermal, electrochemical, and photochemical investigation. |
|---|---|
| المؤلفون: | Frizon TEA; Department of Energy and Sustainability, Federal University of Santa Catarina, Araranguá, SC, Brazil. Electronic address: tiago.frizon@ufsc.br., Salla CAM; Physics Department, Federal University of Santa Catarina, Florianópolis, SC, Brazil., Grillo F; Department of Materials and Metallurgy, Federal Institute of Espírito Santo, Vitória, ES, Brazil., Rodembusch FS; Institute of Chemistry, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil., Câmara VS; Institute of Chemistry, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil., Silva HC Jr; Institute of Chemistry, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil., Zapp E; Department of Exact Sciences and Education, Federal University of Santa Catarina, Blumenau, SC, Brazil., Junca E; University of the Extreme South of Santa Catarina (UNESC), Criciúma, SC, Brazil., Galetto FZ; Department of Chemistry, Federal University of Santa Catarina, Florianópolis, SC, Brazil., de Costa AM; Department of Energy and Sustainability, Federal University of Santa Catarina, Araranguá, SC, Brazil., Pedroso GJ; Department of Energy and Sustainability, Federal University of Santa Catarina, Araranguá, SC, Brazil., Chepluki AA; Department of Energy and Sustainability, Federal University of Santa Catarina, Araranguá, SC, Brazil., Saba S; Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil., Rafique J; Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil; Institute of Chemistry, Federal University of Mato Grosso do Sul, Campo Grande, MS, Brazil. |
| المصدر: | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2023 Mar 05; Vol. 288, pp. 122050. Date of Electronic Publication: 2022 Nov 04. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Elsevier Country of Publication: England NLM ID: 9602533 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-3557 (Electronic) Linking ISSN: 13861425 NLM ISO Abbreviation: Spectrochim Acta A Mol Biomol Spectrosc Subsets: PubMed not MEDLINE; MEDLINE |
| أسماء مطبوعة: | Publication: Original Publication: [Kidlington, Oxford, U.K. ; Tarrytown, NY] : Pergamon, c1994- |
| مستخلص: | This study describes the synthesis of new pyromellitic diimide (PMDI) derivatives obtained in good yields from the reaction between pyromellitic dianhydride and aminobenzazoles reactive to proton-transfer in the excited state (ESIPT). In this investigation, a non-ESIPT PMDI was also prepared for comparison. These compounds presented absorption maxima in the ultraviolet region attributed to the allowed 1 π-π* electronic transitions. Redshifted absorptions were observed for the ESIPT compounds (3b-3c) due to their π-extended conjugation if compared to the non-ESIPT dye (3a). The compounds presented fluorescence emissions between 300 and 600 nm, dependent on the solvent polarity and their chemical structures. While compound 3a presents a single emission, a dual fluorescence could be observed for compounds 3b-3c. As expected for ESIPT compounds, the emission at higher energies could be related to the excited enol conformer (E*), and the emission with a large Stokes shift was attributed to the keto tautomer (K*). All compounds presented fluorescence emission in the solid state, whereas the ESIPT derivatives presented redshifted emissions with a large Stokes shift, as expected. Cyclic voltammetry was employed to investigate the electrochemical properties of these compounds. The HOMO and LUMO energy levels were estimated at -5.40 to -5.00 eV and -2.84 to -2.62 eV, and good thermal stability (T Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. (Copyright © 2022 Elsevier B.V. All rights reserved.) |
| فهرسة مساهمة: | Keywords: Benzazoles; ESIPT; Fluorescence; PMDI; Proton-transfer |
| تواريخ الأحداث: | Date Created: 20221210 Date Completed: 20230109 Latest Revision: 20230111 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1016/j.saa.2022.122050 |
| PMID: | 36495682 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1873-3557 |
|---|---|
| DOI: | 10.1016/j.saa.2022.122050 |