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

Mateusz Gierszewski

Abstract

Spectral and photophysical properties of 5-deazaalloxazine (5DAll), its methyl derivatives, 10-ethyl-5-deazaisoalloxazine (10Et-5DIzoAll) and alloxazine derivatives with four ring structure have been investigated using experimental and theoretical approach. UV/Vis absorption and emission spectroscopy have been used to describe the electronic structure of studied molecules. Values of the fluorescence quantum yield determined are relatively high, the fluorescence lifetimes are relatively long comparing to respective alloxazines. Both spectral and photophysical properties of 10Et-5DIzoAll and 5DAll derivatives are different as compared to the respective iso- and alloxazines. The electronic structures of molecules and the predicted energies of singlet → singlet, singlet → triplet and triplet → triplet transitions have been determined using the DFT and ab-inito methods. For 5DAll derivatives and for alloxazine derivatives with four ring structure the S0→S1 transition has been found having π,π* character. The triplet lifetime for 5DAll derivatives have been found in a microsecond time range. It has been found that 5DAll derivatives can be used as efficient photosensitizers of singlet oxygen. The applications of the synchronous fluorescence spectroscopy have been implemented, especially in studies of mixtures of flavin and 5-deazaflavin type of compounds.
Record ID
UAMceee876028934e74984b134903556a23
Diploma type
Doctor of Philosophy
Author
Title in Polish
Spektroskopia i fotofizyka pochodnych 5-deazaalloksazyny. Ujęcie eksperymentalne i teoretyczne
Title in English
Spectroscopy and photophysics of 5-deazaalloxazine derivatives. Experimental and theoretical approaches
Language
pol (pl) Polish
Certifying Unit
Wydział Chemii [nowa struktura organizacyjna] (SNŚ/WC)
Scientific discipline (2.0)
6.5 chemical sciences
Status
Finished
Year of creation
2015
Defense Date
15-06-2015
Title date
15-06-2015
Supervisor
URL
https://hdl.handle.net/10593/13251 Opening in a new tab
Keywords in English
Spectroscopy, Photophysics, Flawins, Tlen singletowy, 5-deazaalloxazines
Abstract in English
Spectral and photophysical properties of 5-deazaalloxazine (5DAll), its methyl derivatives, 10-ethyl-5-deazaisoalloxazine (10Et-5DIzoAll) and alloxazine derivatives with four ring structure have been investigated using experimental and theoretical approach. UV/Vis absorption and emission spectroscopy have been used to describe the electronic structure of studied molecules. Values of the fluorescence quantum yield determined are relatively high, the fluorescence lifetimes are relatively long comparing to respective alloxazines. Both spectral and photophysical properties of 10Et-5DIzoAll and 5DAll derivatives are different as compared to the respective iso- and alloxazines. The electronic structures of molecules and the predicted energies of singlet → singlet, singlet → triplet and triplet → triplet transitions have been determined using the DFT and ab-inito methods. For 5DAll derivatives and for alloxazine derivatives with four ring structure the S0→S1 transition has been found having π,π* character. The triplet lifetime for 5DAll derivatives have been found in a microsecond time range. It has been found that 5DAll derivatives can be used as efficient photosensitizers of singlet oxygen. The applications of the synchronous fluorescence spectroscopy have been implemented, especially in studies of mixtures of flavin and 5-deazaflavin type of compounds.
Thesis file
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Uniform Resource Identifier
https://researchportal.amu.edu.pl/info/phd/UAMceee876028934e74984b134903556a23/
URN
urn:amu-prod:UAMceee876028934e74984b134903556a23

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