Excited State Intramolecular Proton Transfer Dynamics of 1-Hydroxy-2-acetonaphthone

Kim, Jin–Yong; Heo, Wooseok; Joo, Taiha

doi:10.1021/jp5088306

Cited by 41 publications

(37 citation statements)

References 63 publications

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“…Research Articles of t 1 = 0.2 ps and t 2 = 1.7 ps,and alonger decay component of t 3 = 18.1 ps.T he fast relaxation decays of t 1 = 0.2 ps is attributed to the lattice relaxation. [32] Fort he detection at 850 nm, the dynamic is composed by ar ise component of t rise = 1.6 ps and as ingle-exponential decay with the lifetime of t = 216.8 ps,t he latter can be assigned to the lifetime of TB*. It can be clearly seen that the fast relaxation decay of t 2 = 1.7 ps of TA*m atches well with the rise component of t rise = 1.6 ps of TB*, revealing that the second proton transfer occurs in this time range.I na ddition, the longer decay component of TB* (216.8 ps) is much longer than that of TA* (18.1 ps), indicating that the transition from TB* to TA* (reverse proton transfer) cannot happen.…”

Section: Chemiementioning

confidence: 99%

Cascaded Excited‐State Intramolecular Proton Transfer Towards Near‐Infrared Organic Lasers Beyond 850 nm

Zhuo

Lai

et al. 2021

Angew Chem Int Ed

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Near-infrared (NIR) organic solid-state lasers play an essential role in applications ranging from laser communication to infrared night vision, but progress in this area is restricted by the lack of effective excited-state gain processes. Herein, we originally proposed and demonstrated the cascaded occurrence of excited-state intramolecular proton transfer for constructing the completely new energy-level systems.Cascading by the first ultrafast proton transfer of < 430 fs and the subsequent irreversible second proton transfer of ca. 1.6 ps,the stepwise proton transfer process favors the true six-level photophysical cycle,w hichs upports efficient population inversion and thus NIR single-mode lasing at 854 nm. This work realizes longest wavelength beyond 850 nm of organic single-crystal lasing to date and originally exploits the cascaded excited-state molecular proton transfer energy-level systems for organic solid-state lasers.

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Section: Chemiementioning

confidence: 99%

Cascaded Excited‐State Intramolecular Proton Transfer Towards Near‐Infrared Organic Lasers Beyond 850 nm

Zhuo

Lai

et al. 2021

Angew Chem Int Ed

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“…‡ ‡ Our data by ultra-fast spectroscopy indicate that W 322 H + is less stabilized in the WT than in the Y373F mutant; see Section 4.1.2. 0.6 Å in the excited state of 1-hydroxy-2-acetonaphtone 90 or at most a few picoseconds over approx.…”

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confidence: 99%

Ultrafast Oxidation of a Tyrosine by Proton-Coupled Electron Transfer Promotes Light Activation of an Animal-like Cryptochrome

et al. 2019

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The animal-like cryptochrome of Chlamydomonas reinhardtii (CraCRY) is a recently discovered photoreceptor that controls the transcriptional profile and sexual life cycle of this alga by both blue and red light. CraCRY has the uncommon feature of efficient formation and longevity of the semi-reduced neutral form of its FAD cofactor upon blue light illumination. Tyrosine Y 373 plays hereby a crucial role by elongating as fourth member the electron transfer (ET) chain that comprises the tryptophan triad otherwise found in most other cryptochromes and DNA photolyases. Here, we report the full mechanism of light-induced FADH • formation in CraCRY using transient absorption spectroscopy from hundreds of femtoseconds to seconds. Electron transfer starts from ultrafast reduction of excited FAD to FAD •by the proximal tryptophan (0.4 ps) and is followed by delocalized migration of the produced WH •+ radical along the tryptophan triad (3.7 and 55 ps). Oxidation of Y 373 by coupled ET to WH •+ and deprotonation then proceeds in ~800 ps, without any significant kinetic isotope effect, nor a pH effect between pH 6.5 and 9.0. The FAD •-/Y 373 • pair is formed with high quantum yield (~60%); its intrinsic decay by recombination is slow (~50 ms), favoring reduction of Y 373 • by extrinsic agents and protonation of FAD •to form the long-lived, red-light absorbing FADH • species. Possible mechanisms of tyrosine oxidation by ultrafast proton-coupled ET in CraCRY, a process about 40 times faster than the archetypal tyrosine-Z oxidation in photosystem II, are discussed in detail.

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“…Excitation of I result in ESIPT from the pre‐formed six membered intramolecularly hydrogen bonded 2‐hydroxy benzaldehyde fragment, resulting a largely Stokes shifted fluorescence from the protonated keto ( Ia ) form at 420 nm in 1,4‐dioxane and acetonitrile. Although, the magnitude of Stokes shift is comparatively less than the standard ESIPT systems, Δν ss value even as low as 6000 cm −1 is reported for several ESIPT systems . Further, the excited I* form can also undergo carboxylic proton dissociation to generate mono‐anionic III* in moderate proton accepting solvent like methanol.…”

Section: Resultsmentioning

confidence: 96%

Excited State Decay Dynamics in 3‐Formyl‐4‐hydroxy Benzoic Acid: Understanding the Global Picture of an ESIPT‐Driven Multiple‐Emissive Species

et al. 2019

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Relaxation dynamics of excited state intramolecular proton transfer (ESIPT) probe 3‐formyl‐4‐hydroxy benzoic acid (FHBA) was studied by steady state, nanosecond time‐resolved fluorescence (TRF) and femtosecond transient absorption (TA) experiments in combination with adequate level of quantum chemical calculations. Global analysis of the transient data with target model reveals that enol conformers of both the neutral FHBA (I) and proton dissociated mono‐anionic species (III) undergo ESIPT in picosecond time scale (τESIPT ≈1.2 ps) towards the formation of corresponding vibrationally hot keto structure. Rapid intramolecular vibrational cooling (τ≈20 ps) follows singlet deactivation of the corresponding conformers with fluorescence lifetime (τfluo) of ∼5.1 and 2.0 ns, respectively as confirmed from stimulated emission (SE) and/or time resolved fluorescence experiments. Selective excitation of the di‐anionic structure (II) at 400 nm follows relatively simple excited state non‐ESIPT decay dynamics having fluorescence emission at 500 nm with τfluo ≈ 1.2 ns. Complete optimization of individual structures and construction of ESIPT profile was done by HF(CIS) as well as (TD)DFT calculation using 6–311++G(d,p) basis set and found to be consistent with the experimental observations.

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Excited State Intramolecular Proton Transfer Dynamics of 1-Hydroxy-2-acetonaphthone

Cited by 41 publications

References 63 publications

Cascaded Excited‐State Intramolecular Proton Transfer Towards Near‐Infrared Organic Lasers Beyond 850 nm

Cascaded Excited‐State Intramolecular Proton Transfer Towards Near‐Infrared Organic Lasers Beyond 850 nm

Ultrafast Oxidation of a Tyrosine by Proton-Coupled Electron Transfer Promotes Light Activation of an Animal-like Cryptochrome

Excited State Decay Dynamics in 3‐Formyl‐4‐hydroxy Benzoic Acid: Understanding the Global Picture of an ESIPT‐Driven Multiple‐Emissive Species

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