Spectroscopy and photophysics of trimethyl-substituted derivatives of 5-deazaalloxazine. Experimental and theoretical approaches

Dorota Prukała , Mateusz Gierszewski , Maciej Kubicki , Tomasz Pędziński , Ewa Sikorska , Marek Sikorski

Abstract

Photophysical and structural properties of 5-deazaalloxazine derivatives were studied, with methyl substituent at the position 8 or 9 of the benzene ring and at the N(1) and N(3) positions. Crystal structures of the compounds were determined by X-ray diffraction method. Electronic structure and S0 → Si, S0 → Ti and T1 → Ti transition energies and oscillator strengths were calculated for 1,3,8- and 1,3,9-trimethyl-5-deazaalloxazine, using the TD-DFT methods. The calculations suggest that for 5-deazaalloxazine derivatives the lowest-lying singlet excited states have pure π,π∗ nature. This is in contrast to the alloxazine derivatives, where two lowest-lying transitions are of π,π∗ and n,π∗ character, being isoenergetic in most cases. The theoretical data are compared to the experimental results, involving steady-state and time-resolved spectra. 1,3,8-Trimethyl-5-deazaalloxazine and 1,3,9-trimethyl-5-deazaalloxazine have longer fluorescence lifetimes and higher values of fluorescence quantum yield compared to the alloxazine derivatives in the same solvents, whereas the absorption maxima and emission maxima of studied compounds are blue-shifted as compared to trimethyl derivatives of alloxazine.
Author Dorota Prukała - University Adam Mickiewicz in Poznań
Dorota Prukała,,
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, Mateusz Gierszewski - University Adam Mickiewicz in Poznań
Mateusz Gierszewski,,
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, Maciej Kubicki - University Adam Mickiewicz in Poznań
Maciej Kubicki,,
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, Tomasz Pędziński - University Adam Mickiewicz in Poznań
Tomasz Pędziński,,
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, Ewa Sikorska (WT / KTiAI)
Ewa Sikorska,,
- Department of Technology and Instrumental Analysis
, Marek Sikorski - Adam Mickiewicz University (UAM)
Marek Sikorski,,
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Journal seriesJournal of Molecular Structure, ISSN 0022-2860, (A 20 pkt)
Issue year2015
No1079
Pages139-146
Publication size in sheets0.5
Keywords in EnglishAlloxazines, 5-Deazaalloxazines, DFT study, Photophysics, UV–Vis spectroscopy, X-ray crystallography
ASJC Classification1602 Analytical Chemistry; 1604 Inorganic Chemistry; 1605 Organic Chemistry; 1607 Spectroscopy
DOIDOI:10.1016/j.molstruc.2014.09.028
Languageen angielski
Score (nominal)20
Score sourcejournalList
ScoreMinisterial score = 20.0, 30-12-2019, ArticleFromJournal
Ministerial score (2013-2016) = 20.0, 30-12-2019, ArticleFromJournal
Publication indicators WoS Citations = 1; Scopus SNIP (Source Normalised Impact per Paper): 2015 = 0.821; WoS Impact Factor: 2015 = 1.78 (2) - 2015=1.683 (5)
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