Photophysical properties of alloxazine derivatives with extended aromaticity – Potential redox-sensitive fluorescent probe

Golczak, Anna; Insińska-Rak, Małgorzata; Davoudpour, Amirali; Saeed, Daban Hama; Ménová, Petra; Mojr, Viktor; Cibulka, Radek; Khmelinskii, I. V.; Mrówczyńska, Lucyna; Sikorski, Marek

doi:10.1016/j.saa.2022.120985

Cited by 5 publications

(3 citation statements)

References 42 publications

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“…Thus, the bathochromic shift of the absorption bands, which is desirable for visible light photoredox catalysis, allowed to move maximum of up to 473 nm (for 2bm ). This value is not as high as the shift to about 543 nm caused by the extension of the alloxazine benzene ring to anthracene or pyrene . Nevertheless, it is sufficient for the application of 2c in visible light photocatalysis.…”

Section: Resultsmentioning

confidence: 92%

“…The redox-related properties of flavins can be influenced by conformational effects, metal ion coordination, donor atom−π interactions, hydrogen bonding, , and π-stacking interactions. , In terms of covalent bonding, the spectral and electronic properties of flavins have been found to be affected by direct substitution of the flavin π-conjugated system . Thus, the desired properties of flavin catalysts are achieved mostly by introducing a simple functional group(s) into position 7 or 8 of the flavin skeleton ,, or by forming flavinium salts. ,, Alternatively, the extension of the flavin π-conjugated system through the replacement of the simple benzene ring in the flavin skeleton with naphthalene, anthracene, or phenanthrene has also been reported . However, to our surprise, no prior study has sought to tune the properties of flavins by installing aryl substituents in position 7 or 8 via direct C–C bonding.…”

Section: Introductionmentioning

confidence: 99%

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Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling

et al. 2022

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Palladium-catalyzed Suzuki reactions of brominated flavin derivatives (5-deazaflavins, alloxazines, and isoalloxazines) with boronic acids or boronic acid esters that occur readily under mild conditions were shown to be an effective tool for the synthesis of a broad range of 7/8-arylflavins. In general, the introduction of an aryl/heteroaryl group by means of a direct C−C bond has been shown to be a promising approach to tuning the photophysical properties of flavin derivatives. The aryl substituents caused a bathochromic shift in the absorption spectra of up to 52 nm and prolonged the fluorescence lifetime by up to 1 order of magnitude. Moreover, arylation of flavin derivatives decreased their ability to generate singlet oxygen.

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Section: Resultsmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling

et al. 2022

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“…A previous study showed the variability of optical, electrochemical, and morphological properties of alloxazine derivatives. This property was applied by Golczak et al in a fluorescence microscopy study of human red blood cells. Presently, flavins are used for the photocatalysis of various oxidative reactionsthe preparation of sulfoxides or some cycloeliminations …”

Section: Introductionmentioning

confidence: 99%

Nature-Inspired Photocatalytic Hydrogen Production with a Flavin Photosensitizer

Ivanová,

Truksa,

Whang

et al. 2024

ACS Omega

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Green hydrogen, by definition, must be produced with renewable energy sources without using fossil fuels. To transform the energy system, we need a fully sustainable production of green and renewable energy as well as the introduction of such "solar fuels" to tackle the chemical storage aspect of renewable energies. Conventional electrolysis of water splitting into oxygen and hydrogen gases is a clean and nonfossil method, but the use of massive noble-metal electrodes makes it expensive. Direct photocatalytic hydrogen evolution in water is an ideal approach, but an industrial scale is not available yet. In this paper, we intend to introduce flavins as metal-free organic photosensitizers for photoinduced reduction processes. Specifically, a flavin photosensitizer was employed for the photocatalytic evolution of hydrogen gas in aqueous media. The ratio of photosensitizer to cocatalyst concentration has been found to affect the efficiency of the hydrogen evolution reaction. Since flavins are nature-inspired molecules (like vitamin B2) with easily tunable properties through structure modification, this family of compounds opens the door for new possibilities in sustainable green hydrogen production.

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Improving Photophysical Properties of Deazaflavin Derivatives by Acrylaldehyde Bridging: A Theoretical Investigation

Guo,

Liu,

Liu

et al. 2024

ChemPhotoChem

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The electronic structure and photophysical properties of several acrylaldehyde‐bridged deazaflavin derivatives (cFLs) were investigated theoretically. The impact of acrylaldehyde bridging on photophysical properties of deazaflavin (cFL) is strongly site‐dependent. Specifically, the change of adiabatic energy of electronic transitions(ΔEad) and vibronic coupling promote fluorescent emission to be comparable to internal conversion of cFL and cFL4 (both C5‐C6 and C9‐N10 bridged, but C9‐N10 bridged by propene), turning them eligible as fluorescent sensors. As El‐Sayed’s rule is satisfied in cFL1(C5‐C6 bridged), cFL2(C9‐N10 bridged) and cFL3(both C5‐C6 and C9‐N10 bridged), intersystem crossing from first singlet excited state to triplet excited states (Tn) become dominant and the evolution of excited cFLs from T1 appears vital. The rate constants of photophysical processes indicate these cFLs are of dominantly high steady state T1 concentration and are potential triplet sensitizers. We expect the findings would pave the way for rational design of novel cFLs with extraordinary photophysical properties.

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Photophysical properties of alloxazine derivatives with extended aromaticity – Potential redox-sensitive fluorescent probe

Cited by 5 publications

References 42 publications

Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling

Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling

Nature-Inspired Photocatalytic Hydrogen Production with a Flavin Photosensitizer

Improving Photophysical Properties of Deazaflavin Derivatives by Acrylaldehyde Bridging: A Theoretical Investigation

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