Unusual behavior in di-substituted piperidine and piperazine anthraquinones upon protonation - spectral, electrochemical, and quantum chemical studies

Anna Wcisło , Iwona Dąbkowska , Justyna Czupryniak , Tadeusz Ossowski , Dorota Zarzeczańska


The objective of the study is to determine the influence of a substituent on the spectroscopic and electrochemical properties of a series of novel 9,10‑anthraquinone piperidine and piperazine derivatives.We conducted UV–Vis spectroscopy, pH-spectroscopic titration, and cyclic voltammetry measurements with an interesting phenomenon observed in the case of di-substituted quinones. Compounds with substituents in position 1 and 8 exhibit a significant increase in the absorption intensity of the monoprotonated form. Spectroscopic studies in the conjunction with time-dependent density functional theory (TD-DFT) calculations were employed to explore the unusual behavior. The state-of-the-art quantum chemistry calculations including bulk solvent in the polarizable continuum model (PCM) enabled the study of prototropic tautomerization and its influence on the position of absorption bands. The results of cyclic voltammetry measurements allowed us to determine the deciding factor influencing the reduction – the number of substituents and the possibility of the hydrogen bond formation of the charged states.
Author Anna Wcisło (FCh/DACh/LSCh)
Anna Wcisło,,
- Laboratory of Supramolecular Chemistry
, Iwona Dąbkowska (FCh/DACh/LSCh)
Iwona Dąbkowska,,
- Laboratory of Supramolecular Chemistry
, Justyna Czupryniak (FCh/DACh/LSCh)
Justyna Czupryniak ,,
- Laboratory of Supramolecular Chemistry
, Tadeusz Ossowski (FCh/DACh/LSCh)
Tadeusz Ossowski,,
- Laboratory of Supramolecular Chemistry
, Dorota Zarzeczańska (FCh/DACh/LSCh)
Dorota Zarzeczańska,,
- Laboratory of Supramolecular Chemistry
Journal seriesJournal of Molecular Liquids, ISSN 0167-7322, (N/A 100 pkt)
Issue year2019
Publication size in sheets0.50
Keywords in EnglishSpectroscopy, electrochemistry, intramolecular charge transfer, protolytic forms, TD-DFT, theoretical UV-Vis spectra
ASJC Classification2505 Materials Chemistry; 1606 Physical and Theoretical Chemistry; 1607 Spectroscopy; 3104 Condensed Matter Physics; 3107 Atomic and Molecular Physics, and Optics; 2504 Electronic, Optical and Magnetic Materials
URL https://doi.org/10.1016/j.molliq.2019.01.115
Languageen angielski
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 28-01-2020, ArticleFromJournal
Publication indicators WoS Citations = 1.000; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 1.275; WoS Impact Factor: 2018 = 4.561 (2) - 2018=4.136 (5)
Citation count*1 (2020-07-04)
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