Excited state intramolecular proton transfer of 1,2-dihydroxyanthraquinone by femtosecond transient absorption spectroscopy

Lee, Sebok; Lee, Jaebeom; Pang, Yoonsoo

doi:10.1016/j.cap.2015.08.017

Cited by 41 publications

(48 citation statements)

References 42 publications

(23 reference statements)

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“…The τ D was measured as 2.63 ns from a separate time-correlated single photon counting (TCSPC) measurement (See Supplemenatry page 17) 43 . The energy transfer efficiency ( E ) of ZnTPP → fbTPP was also evaluated using E = 1 − τ DA /τ D , resulting in 97.6–96.3% for Zn( i + 2) - Zn( i + 6) .…”

Section: Resultsmentioning

confidence: 99%

Precisely tuneable energy transfer system using peptoid helix-based molecular scaffold

Kang

Yang

Lee

et al. 2017

Sci Rep

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The energy flow during natural photosynthesis is controlled by maintaining the spatial arrangement of pigments, employing helices as scaffolds. In this study, we have developed porphyrin-peptoid (pigment-helix) conjugates (PPCs) that can modulate the donor-acceptor energy transfer efficiency with exceptional precision by controlling the relative distance and orientation of the two pigments. Five donor-acceptor molecular dyads were constructed using zinc porphyrin and free base porphyrin (Zn(i + 2)–Zn(i + 6)), and highly efficient energy transfer was demonstrated with estimated efficiencies ranging from 92% to 96% measured by static fluorescence emission in CH2Cl2 and from 96.3% to 97.6% using femtosecond transient absorption measurements in toluene, depending on the relative spatial arrangement of the donor-acceptor pairs. Our results suggest that the remarkable precision and tunability exhibited by nature can be achieved by mimicking the design principles of natural photosynthetic proteins.

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Section: Resultsmentioning

confidence: 99%

Precisely tuneable energy transfer system using peptoid helix-based molecular scaffold

Kang

Yang

Lee

et al. 2017

Sci Rep

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“…The excess energy in the 405-nm excitation may facilitate the ESIPT by overcoming the energy barrier of the LE-PT tautomerization. Concentration and wavelength dependences in the emission spectra of alizarin can be the evidence for the existence of the energy barrier between the LE and PT tautomers [19,20,41].…”

Section: Steady-state Absorption and Emission Spectra Of Alizarinmentioning

confidence: 99%

“…It has been proposed that faster components of 300-400 fs time constant generally observed from the transient absorption signals of alizarin in the wavelengths (570-585 nm) where the strong ESA and SE signals cancel out, may represent the kinetics for the vibrational relaxation in the LE tautomer and the ESIPT to the PT tautomer [41,43]. We also observed these fast components universally in the transient absorption results of alizarin in ethanol, methanol, DMSO, and ethanolwater mixture (examples are shown in Figure 4(c) and (d)), but did not show any dependence on the solvent polarity.…”

Section: Excited State Intramolecular Proton Transfer Of Alizarin 41mentioning

confidence: 99%

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Ultrafast Intramolecular Proton Transfer Reaction of 1,2- Dihydroxyanthraquinone in the Excited State

Lee¹,

Jen²,

Jeon³

et al. 2018

Photochemistry and Photophysics - Fundamentals to Applications

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1,2-Dihydroxyanthraquinone (alizarin) shows an ultrafast intramolecular proton transfer in the excited states between the adjacent hydroxyl and carbonyl groups. Due to the ground and electronic structure of locally excited and proton-transferred tautomers, alizarin shows dual emission bands with strong Stokes shifts. The energy barriers between the locally excited (LE) and proton-transferred (PT) tautomers in the excited state are strongly dependent on the solvent polarity and thus alizarin shows complicated photophysical properties including solvent and excitation dependences. The excited-state intramolecular proton transfer (ESIPT) of alizarin was monitored in time-resolved stimulated Raman spectroscopic investigation, where the instantaneous structural changes of anthraquinone backbone in 70~80 fs were captured. Two major vibrational modes of alizarin, ν(C=C) and ν(C=O) represent the proton transfer reaction in the excited state, which then leads to the vibrational relaxation of the product and the restructuring of solvent molecules. Ultrafast changes in solvent vibrational modes of dimethyl sulfoxide (DMSO) were also investigated for the solvation dynamics including hydrogen bond breaking and reformation.

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Effects of solvents on excited‐state proton transfer behaviors and photophysical properties of 3NTF

Lin

Xie

Xiao

et al. 2023

J of Physical Organic Chem

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In this work, we systematically investigate the effects of solvent on the mechanism of excited‐state proton transfer and photophysical properties of 3NTF using density functional and time‐dependent density functional. The geometry of 3NTF (normal structure and isomer structure) was optimized. Based on the optimized geometry, the parameters related to hydrogen bond indicate that the hydrogen bond is strengthened in the S1 state. Further, reduced density gradient functions provide a more intuitive proof of the excited hydrogen bond strengthening mechanism. The analysis of frontier molecular orbitals shows that the charge density of the S0 and S1 states has changed significantly, which is the driving force for proton transfer in the excited state. The infrared vibrational spectra show that the hydrogen bond strength decreases with the increase of solvent polarity. The absorption and fluorescence spectra of the molecules are very sensitive to the solvent polarity. Through the analysis of the potential energy curves, it is concluded that the decrease of solvent polarity will promote the occurrence of the excited state proton transfer process.

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Excited state intramolecular proton transfer of 1,2-dihydroxyanthraquinone by femtosecond transient absorption spectroscopy

Cited by 41 publications

References 42 publications

Precisely tuneable energy transfer system using peptoid helix-based molecular scaffold

Precisely tuneable energy transfer system using peptoid helix-based molecular scaffold

Ultrafast Intramolecular Proton Transfer Reaction of 1,2- Dihydroxyanthraquinone in the Excited State

Effects of solvents on excited‐state proton transfer behaviors and photophysical properties of 3NTF

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