Spectroscopy and photophysics of dimethyl-substituted alloxazines

Sikorski, Marek; Prukała, Dorota; Insińska-Rak, Małgorzata; Khmelinskii, Igor; Worrall, David R.; Williams, Siân L.; Hernando, Jordi; Bourdelande, J. L.; Koput, Jacek; Sikorska, Ewa

doi:10.1016/j.jphotochem.2008.07.006

Cited by 23 publications

(22 citation statements)

References 61 publications

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“…The increase in fluorescence quantum yields can also be observed for alloxazines in protic solvents . The fluorescence lifetimes of the 5‐deazaalloxazines are longer if compared to their “aza” analogs . Note that the N(1), N(3)‐substituted 1,3Me‐5‐DAll has shorter fluorescence lifetimes than its unsubstituted analog 5‐DAll.…”

Section: Resultsmentioning

confidence: 81%

“…This simultaneously causes a reduction in the S 1 to T 1 radiationless intersystem crossing (ISC) rates . The increase in fluorescence quantum yields can also be observed for alloxazines in protic solvents . The fluorescence lifetimes of the 5‐deazaalloxazines are longer if compared to their “aza” analogs .…”

Section: Resultsmentioning

confidence: 82%

“…Based on our earlier calculations that used time‐dependent density functional theory (TD‐DFT), all the tested derivatives of alloxazine have two pairs of closely located n , π * and π , π * transitions in the lowest energy part of the spectrum . Contrary to that, the transitions in the lowest energy part of the absorption spectrum of 5‐DAll and 1,3Me‐5‐DAll have pure π , π * character, as we predict and present in the Discussion section.…”

Section: Introductionmentioning

confidence: 99%

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Photophysics, Excited‐state Double‐Proton Transfer and Hydrogen‐bonding Properties of 5‐Deazaalloxazines

Prukała

Khmelinskii

Koput

et al. 2014

Photochem & Photobiology

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The photophysical properties of 5-deazaalloxazine and 1,3-dimethyl-5-deazaalloxazine were studied in different solvents. These compounds have higher values of fluorescence quantum yields and longer fluorescence lifetimes, compared to those obtained for their alloxazine analogs. Electronic structure and S0 -Si transitions were investigated using the ab initio methods [MP2, CIS(D), EOM-CCSD] with the correlation-consistent basis sets. Also the time-dependent density functional theory (TD-DFT) has been employed. The lowest singlet excited states of 5-deazaalloxazine and 1,3-dimethyl-5-deazaalloxazine are predicted to have the π, π* character, whereas similar alloxazines have two close-lying π, π* and n, π* transitions. Experimental steady-state and time-resolved spectral studies indicate formation of an isoalloxazinic excited state via excited-state double-proton transfer (ESDPT) catalyzed by an acetic acid molecule that forms a hydrogen bond complex with the 5-deazaalloxazine molecule. Solvatochromism of both 5-deazaalloxazine and its 1,3-dimethyl substituted derivative was analyzed using the Kamlet-Taft scale and four-parameter Catalán solvent scale. The most significant result of our studies is that the both scales show a strong influence of solvent acidity (hydrogen bond donating ability) on the emission properties of these compounds, indicating the importance of intermolecular solute-solvent hydrogen-bonding interactions in their excited state.

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Section: Resultsmentioning

confidence: 81%

Section: Resultsmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

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Photophysics, Excited‐state Double‐Proton Transfer and Hydrogen‐bonding Properties of 5‐Deazaalloxazines

Prukała

Khmelinskii

Koput

et al. 2014

Photochem & Photobiology

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“…Furthermore, some molecules are highly sensitive to the change in the microenvironments, based on which Sytnik et al reported how the ESIPT chromophores can be used in the study of protein conformations and binding site polarity . Indeed, a lot of spectroscopic techniques were applied to study the ESIPT process in recent years, while the studies about ESIPT still have numerous challenges. That is to say, although lots of endeavors have been dedicated, the intrinsic complicated properties of physics and chemistry are still confused, for example, nuclear rearrangement, formation or cleavage of hydrogen bond wires, variations of excited state hydrogen bond, and so on.…”

Section: Introductionmentioning

confidence: 99%

Solvent controlling excited state proton transfer reaction in quinoline/isoquinoline‐pyrazole isomer QP‐I: A theoretical study

Yang

Zhao

et al. 2017

J of Physical Organic Chem

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In this present work, we theoretically study the excited state intramolecular proton transfer (ESIPT) mechanism about a quinoline/isoquinoline‐pyrazole isomer QP‐I system. Compared with previous experimental results, our calculated results reappear previous data, which further confirm the theoretical level we used is reasonable. We mainly adopt 2 kinds of solvents (nonpolar cyclohexane and polar acetonitrile) to explore solvents effects on this system. Through reduced density gradient (RDG) function, the intramolecular hydrogen bond N1─H2···N3 has been confirmed existing in both S0 and S1 states, although the distance between H2 and N3 is not short. In addition, the strengthening N1─H2···N3 in the S1 state provides possibility for ESIPT. Explorations about charge redistribution reveal the trend of ESIPT, and frontier orbital gap reflects the reactivity in polar and nonpolar solvents. The constructing potential energy curves reveal that potential energy barriers could be controlled and regulated by solvent polarity.

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“…-Flavins play an important role in living organisms [1], and they are involved in several important photobiological and photochemical processes, such as phototropism, phototaxis, and photodynamic action [2] [3]. Since 1966, the photochemistry and photophysics of alloxazine derivatives have been studied, due to the discovery of the proton-transfer reactions in lumichrome and related compounds [4] [5].…”

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confidence: 99%

Synthesis of Flavin–Calix[4]arene Conjugate Derivatives

Sayın

Akkuş

Cibulka

et al. 2011

Helvetica Chimica Acta

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The synthesis of two new flavin substituted calix [4]arene derivatives, 9 and 10, is described. The first flavin substituted calix[4]arene derivative 9 was synthesized by the reaction of 3-methylalloxazine (5) with 25,27-bis(3-bromopropoxy)-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene (4) in high yield (92%). The other derivative 10 was prepared from 3-methylalloxazine-1-acetic acid (7) and 25,27-bis(3-cyanopropoxy)calix[4]arene (3). All new compounds were characterized by a combination of FT-IR and 1 H-NMR spectroscopy, and elemental-analysis techniques.

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Spectroscopy and photophysics of dimethyl-substituted alloxazines

Cited by 23 publications

References 61 publications

Photophysics, Excited‐state Double‐Proton Transfer and Hydrogen‐bonding Properties of 5‐Deazaalloxazines

Photophysics, Excited‐state Double‐Proton Transfer and Hydrogen‐bonding Properties of 5‐Deazaalloxazines

Solvent controlling excited state proton transfer reaction in quinoline/isoquinoline‐pyrazole isomer QP‐I: A theoretical study

Synthesis of Flavin–Calix[4]arene Conjugate Derivatives

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