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Journal articles on the topic 'Excited State Proton Transfer (ESPT)'

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Author: Grafiati

Published: 7 September 2023

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1

Wu, Chia-Hua, Lucas José Karas, Henrik Ottosson, and Judy I.-Chia Wu. "Excited-state proton transfer relieves antiaromaticity in molecules." Proceedings of the National Academy of Sciences 116, no. 41 (September 25, 2019): 20303–8. http://dx.doi.org/10.1073/pnas.1908516116.

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Baird’s rule explains why and when excited-state proton transfer (ESPT) reactions happen in organic compounds. Bifunctional compounds that are [4n + 2] π-aromatic in the ground state, become [4n + 2] π-antiaromatic in the first 1ππ* states, and proton transfer (either inter- or intramolecularly) helps relieve excited-state antiaromaticity. Computed nucleus-independent chemical shifts (NICS) for several ESPT examples (including excited-state intramolecular proton transfers (ESIPT), biprotonic transfers, dynamic catalyzed transfers, and proton relay transfers) document the important role of excited-state antiaromaticity. o-Salicylic acid undergoes ESPT only in the “antiaromatic” S1 (1ππ*) state, but not in the “aromatic” S2 (1ππ*) state. Stokes’ shifts of structurally related compounds [e.g., derivatives of 2-(2-hydroxyphenyl)benzoxazole and hydrogen-bonded complexes of 2-aminopyridine with protic substrates] vary depending on the antiaromaticity of the photoinduced tautomers. Remarkably, Baird’s rule predicts the effect of light on hydrogen bond strengths; hydrogen bonds that enhance (and reduce) excited-state antiaromaticity in compounds become weakened (and strengthened) upon photoexcitation.

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2

Jouvet, Christophe, Mitsuhiko Miyazaki, and Masaaki Fujii. "Revealing the role of excited state proton transfer (ESPT) in excited state hydrogen transfer (ESHT): systematic study in phenol–(NH3)n clusters." Chemical Science 12, no. 11 (2021): 3836–56. http://dx.doi.org/10.1039/d0sc06877b.

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A general model of excited state hydrogen transfer (ESHT) which unifies ESHT and the excited state proton transfer (ESPT) is presented from experimental and theoretical works on phenol–(NH₃)n. The hidden role of ESPT is revealed.

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3

Wei, Qiang, Jiyu Wang, Meiyu Zhao, Meixia Zhang, Yuzhi Song, and Peng Song. "A theoretical investigation on excited-state single or double proton transfer process for aloesaponarin I." Canadian Journal of Chemistry 96, no. 1 (January 2018): 83–88. http://dx.doi.org/10.1139/cjc-2017-0533.

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The excited-state proton transfer (ESPT) dynamical behavior of aloesaponarin I (ASI) was studied using density functional theory (DFT) and time-dependent DFT (TDDFT) methods. Our calculated vertical excitation energies based on TDDFT reproduced the experimental absorption and fluorescence spectra well [Nagaoka et al. J. Phys. Chem. B, 117, 4347 (2013)]. Two intramolecular hydrogen bonds were confirmed to be strengthened in the S1 state, which makes ESPT possible. Herein, the ESPT process is more likely to happen, along with one hydrogen bond (O1–H2⋯O3). Qualitative analyses about charge distribution further demonstrate that the ESPT process could occur because of the intramolecular charge transfer. Our constructed potential energy surfaces of both S0 and S1 states show that a single proton transfer reactive is more reasonable along with the intramolecular hydrogen bond (O1–H2⋯O3) rather than O4–H5⋯O6 in the S1 stated potential energy surface. Then, ASI-SPT* decays to the ground state with a 640 nm fluorescence; subsequently, the ASI-SPT form shows that reverse ground state single-proton transfer back to the ASI structure occurs. Particularly, dependent on relatively accurate potential energy barriers among these excited-state stable structures, we confirmed the excited-state single proton transfer process rather than using the controversial nodal plane model.

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4

Pina, João, Mohamed Alnady, Anika Eckert, Ullrich Scherf, and J. Sérgio Seixas de Melo. "Alternating donor–acceptor indigo-cyclopentadithiophene copolymers: competition between excited state conformational relaxation, energy transfer and excited state proton transfer." Materials Chemistry Frontiers 2, no. 2 (2018): 281–90. http://dx.doi.org/10.1039/c7qm00439g.

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5

Novitasari, Dian, Hironari Kamikubo, Yoichi Yamazaki, Mariko Yamaguchi, and Mikio Kataoka. "Excited-State Proton Transfer in Fluorescent Photoactive Yellow Protein Containing 7-Hydroxycoumarin." Advanced Materials Research 896 (February 2014): 85–88. http://dx.doi.org/10.4028/www.scientific.net/amr.896.85.

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Green fluorescent protein (GFP) has been used as an effective tool in various biological fields. The large Stokes shift resulting from an excited-state proton transfer (ESPT) is the basis for the application of GFP in such techniques as ratiometric GFP biosensors. The chromophore of GFP is known to be involved in a hydrogen-bonding network. Previous X-ray crystallographic and FTIR studies suggest that a proton wire along the hydrogen-bonding network plays a role in the ESPT. In order to examine the relationship between the ESPT and hydrogen-bonding network within proteins, we prepared an artificial fluorescent protein using a light-sensor protein, photoactive yellow protein (PYP). The native chromophore of p-coumaric acid (pCA) of PYP undergoes trans-cis isomerization after absorbing a photon, which triggers proton transfers within the hydrogen-bonding network comprised of pCA and proximal amino acid residues. Although PYP emits little fluorescence, we succeeded to reconstitute an artificial fluorescent PYP (PYP-coumarin) by substituting the pCA with its trans-lock analog 7-hydroxycoumarin. Spectroscopic studies with PYP-coumarin revealed that the chromophore takes an anionic form at neutral pH, but is protonated by lowering pH. Both the protonated and deprotonated forms of PYP-coumarin emit intense fluorescence, as compared with the native PYP. In addition, both the deprotonated and protonated forms show identical λmax values in their fluorescence spectra, indicating that ESPT occurs in the artificial fluorescent protein.

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6

Basarić, Nikola, Nikola Cindro, Yunyan Hou, Ivana Žabčić, Kata Mlinarić-Majerski, and Peter Wan. "Competing photodehydration and excited-state intramolecular proton transfer (ESIPT) in adamantyl derivatives of 2-phenylphenols." Canadian Journal of Chemistry 89, no. 2 (February 2011): 221–34. http://dx.doi.org/10.1139/v10-102.

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2-Phenylphenol derivatives strategically substituted with a hydroxyadamantyl substituent were synthesized and their photochemical reactivity was investigated. Derivatives 9 and 10 undergo competitive excited-state intramolecular proton transfer (ESIPT) from the phenol to the carbon atom of the adjacent phenyl ring and formal ESPT from the phenol to the hydroxyl group coupled with dehydration. These two processes (both via S1) give rise to two classes of quinone methides (QMs) that revert to starting material or react with nucleophiles, respectively. ESIPT to carbon atoms was studied by performing photolyses in the presence of D2O, whereupon deuterium incorporation to the adjacent phenyl ring was observed ([Formula: see text] = 0.1–0.2). The competing formal ESPT and dehydration takes place with quantum yields that are an order of magnitude lower and was studied by isolation of photomethanolysis products. Derivative 8 did not undergo ESIPT to carbon atom. Owing to the presence of an intramolecular H bond, an efficient ESIPT from the phenol to the hydroxyl group coupled with dehydration gives a QM that efficiently undergoes electrocyclization (overall [Formula: see text] = 0.33), to give chroman 16. In addition, spiro[adamantane-2,9′-(4′-hydroxy)fluorene] (12) undergoes ESIPT, unlike the previously reported unreactive parent 2-hydroxyfluorene. The reactive singlet excited states of the prepared biphenyl and fluorene molecules were characterized by fluorescence spectroscopy, whereas laser flash photolysis (LFP) was performed to characterize the longer lived QM intermediates.

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7

Yang, Dapeng, Jinfeng Zhao, Guang Yang, Nahong Song, Rui Zheng, and Yusheng Wang. "Elaborating the excited-state proton transfer behaviors for novel 3H-MC and P2H-CH." Organic Chemistry Frontiers 4, no. 10 (2017): 1935–42. http://dx.doi.org/10.1039/c7qo00398f.

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8

Yang, Dapeng, and Ruiquan Qi. "Effects of intermolecular hydrogen bonding on the excited-state proton transfer properties of the cinnamonitrile–methanol complex." Canadian Journal of Chemistry 91, no. 3 (March 2013): 229–34. http://dx.doi.org/10.1139/cjc-2012-0368.

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The time-dependent density functional theory (TD-DFT) method was used to study the excited-state proton transfer (ESPT) properties of the hydrogen-bonded cinnamonitrile (3TPAN)–methanol (MeOH) complex (3TPAN–MeOH). The intermolecular hydrogen bonds N1···H11 in both the ground state S0 and the excited state S1 were demonstrated by the optimized geometric structures of the hydrogen-bonded 3TPAN–MeOH complex. While in the excited state S3, a new hydrogen bond H11···O1 was formed after the ESPT took place from the hydrogen-bonded MeOH molecule to the 3TPAN moiety. It was demonstrated that the electronic transitions of the S1 states for both the 3TPAN monomer (including the S3 state) and the hydrogen-bonded 3TPAN–MeOH complex should be of a localized-excited (LE) nature on the 3TPAN molecule, while the S3 state of the hydrogen-bonded 3TPAN–MeOH complex should be of charge transfer (CT) character from the hydrogen-bonded MeOH molecule (through O1···H11) to the 3TPAN moiety. The S3-state proton transfer and charge transfer due to the intermolecular hydrogen-bonding interaction should be the reasons for the remarkable redshift (0.91 eV) of the S3-state electronic energy for the hydrogen-bonded 3TPAN–MeOH complex compared with that of the 3TPAN monomer.

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9

Joshi, Hem C., and Liudmil Antonov. "Excited-State Intramolecular Proton Transfer: A Short Introductory Review." Molecules 26, no. 5 (March 9, 2021): 1475. http://dx.doi.org/10.3390/molecules26051475.

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In this short review, we attempt to unfold various aspects of excited-state intramolecular proton transfer (ESIPT) from the studies that are available up to date. Since Weller’s discovery of ESIPT in salicylic acid (SA) and its derivative methyl salicylate (MS), numerous studies have emerged on the topic and it has become an attractive field of research because of its manifold applications. Here, we discuss some critical aspects of ESIPT and tautomerization from the mechanistic viewpoint. We address excitation wavelength dependence, anti-Kasha ESIPT, fast and slow ESIPT, reversibility and irreversibility of ESIPT, hydrogen bonding and geometrical factors, excited-state double proton transfer (ESDPT), concerted and stepwise ESDPT.

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10

Zhao, Jinfeng, and Peng Li. "The investigation of ESPT for 2,8-diphenyl-3,7-dihydroxy-4H,6H-pyrano[3,2-g]-chromene-4,6-dione: single or double?" RSC Advances 5, no. 90 (2015): 73619–25. http://dx.doi.org/10.1039/c5ra14601a.

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The dynamic overall perspective of an excited-state proton transfer (ESPT) process for 2,8-diphenyl-3,7-dihydroxy-4H,6H-pyrano[3,2-g]-chromene-4,6-dione (D3HF) is investigated based on a time-dependent density functional theory (TDDFT) method.

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11

Guo, Yang Xue, Xiang Hong Kong, Wei Yang, and Jia Jin Zheng. "Study on All Optical Switching Effect of Excited State Proton Transfer Organic Molecule 3-Hydroxyflavone." Advanced Materials Research 482-484 (February 2012): 830–34. http://dx.doi.org/10.4028/www.scientific.net/amr.482-484.830.

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Abstract: We report the dependence of the all optical switching effect of 3-hydroxyflavone (3-HF) on the efficiency of excited state proton transfer (ESPT) using pump probe method. A cw probe laser beam of 632.8nm passing through the sample is switched off by a 35ps pulse pump laser beam of 355nm. We also measured the nonlinear refractive index of 3-HF in different solvents by using z-scan technique. The results show that the optical switching effect will be more obvious when the efficiency of excited state proton transfer is improved, while not proportional to the nonlinear refractive index of 3-HF.

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12

Adamoczky, Anita, Tibor Nagy, Péter Pál Fehér, Veronika Pardi-Tóth, Ákos Kuki, Lajos Nagy, Miklos Zsuga, and Sándor Kéki. "Isocyanonaphthol Derivatives: Excited-State Proton Transfer and Solvatochromic Properties." International Journal of Molecular Sciences 23, no. 13 (June 29, 2022): 7250. http://dx.doi.org/10.3390/ijms23137250.

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Fluorescent probes that exhibit solvatochromic or excited-state proton-transfer (ESPT) properties are essential tools for the study of complex biological or chemical systems. Herein, the synthesis and characterization of a novel fluorophore that reveals both features, 5-isocyanonaphthalene-1-ol (ICOL), are reported. Various solvatochromic methods, such as Lippert–Mataga and Bilot–Kawski, together with time-dependent density functional theory (TD-DFT) and time-resolved emission spectroscopy (TRES), were applied to gain insights into its excited-state behavior. To make comparisons, the octyloxy derivative of ICOL, 5-isocyano-1-(octyloxy)naphthalene (ICON), was also prepared. We found that internal charge transfer (ICT) takes place between the isocyano and –OH groups of ICOL, and we determined the values of the dipole moments for the ground and excited states of both ICOL and ICON. Furthermore, in the emission spectra of ICOL, a second band at higher wavelengths (green emission) in solvents of higher polarities (dual emission), in addition to the band present at lower wavelengths (blue emission), were observed. The extent of this dual emission increases in the order of 2-propanol < methanol < N,N-dimethylformamide (DMF) < dimethyl sulfoxide (DMSO). The presence of the dual fluorescence of ICOL in these solvents can be ascribed to ESPT. For ICOL, we also determined ground- and excited-state pKa values of 8.4 ± 0.3 and 0.9 ± 0.7, respectively, which indicates a considerable increase in acidity upon excitation. The TRES experiments showed that the excited-state lifetimes of the ICOL and ICON spanned from 10.1 ns to 5.0 ns and from 5.7 ns to 3.8 ns, respectively. In addition, we demonstrated that ICOL can be used as an effective indicator of not only the critical micelle concentration (cmc) of ionic (sodium lauryl sulfate (SLS)) and nonionic surfactants (Tween 80), but also other micellar parameters, such as partition coefficients, as well as to map the microenvironments in the cavities of biomacromolecules (e.g., BSA). It is also pointed out that fluorescence quenching by pyridine can effectively be utilized for the determination of the fractions of ICOL molecules that reside at the water–micelle interface and in the interior spaces of micelles.

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13

Yang, Dapeng, Min Jia, Xiaoyan Song, and Qiaoli Zhang. "Elaborating a new excited state intramolecular proton transfer (ESPT) mechanism for a new π-conjugated dye 2, 2′-((5-(2-(4-methoxyphenyl)ethenyl)-benzene-1,1-diyl)-bis-(nitrilomethylylidene)-diphenol)." Canadian Journal of Chemistry 96, no. 3 (March 2018): 351–57. http://dx.doi.org/10.1139/cjc-2017-0628.

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In this work, the excited state dynamical behavior of a novel π-conjugated dye 2,2′-((5-(2-(4-methoxyphenyl)ethenyl)-benzene-1,1-diyl)-bis-(nitrilomethylylidene)-diphenol) (C1) has been investigated. Two intramolecular hydrogen bonds of C1 are tested to pre-existing in the ground state via AIM and reduced density gradient. Using a time-dependent density functional theory (TDDFT) method, it has been substantiated that the intramolecular hydrogen bonds of C1 should be strengthened in the S1 state via analyzing fundamental bond length, bond angles, and corresponding infrared vibrational modes. The most obvious variation of these two hydrogen bonds is the O4–H5···N6 bond, which might play important roles in excited state behavior for the C1 system. Furthermore, based on electronic excitation, charge transfer could occur. Just due to this kind of charge re-distribution, two hydrogen bonds should be tighter in the first excited state, which is consistent with the variation of hydrogen bond lengths. Thus, the phenomenon of charge transfer is reasonable evidence for confirming the occurrence of the excited state proton transfer (ESPT) process in the S1 state. Our theoretically constructed potential energy surfaces of C1 show that excited state single proton transfer should occur along with the O4–H5···N6 hydrogen bond rather than the O1–H2···N3 bond. We not only clarify the ESIPT mechanism for C1 but put forward new affiliation and explain a previous experiment successfully.

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14

Donati, Greta, and Nadia Rega. "Direct or Indirect ESPT Mechanism in CFP psamFP488? A Theoretical-Computational Investigation." International Journal of Molecular Sciences 23, no. 24 (December 9, 2022): 15640. http://dx.doi.org/10.3390/ijms232415640.

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Fluorescent Proteins are widely studied for their multiple applications in technological and biotechnological fields. Despite this, they continue to represent a challenge in terms of a complete understanding of all the non-equilibrium photo-induced processes that rule their properties. In this context, a theoretical-computational approach can support experimental results in unveiling and understanding the processes taking place after electronic excitation. A non-standard cyan fluorescent protein, psamFP488, is characterized by an absorption maximum that is blue-shifted in comparison to other cyan fluorescent proteins. This protein is characterized by an extended Stokes shift and an ultrafast (170 fs) excited state proton transfer. In this work, a theoretical-computational study, including excited state ab initio dynamics, is performed to help understanding the reaction mechanism and propose new hypotheses on the role of the residues surrounding the chromophore. Our results suggest that the proton transfer could be indirect toward the acceptor (Glu167) and involves other residues surrounding the chromophore, despite the ultrafast kinetics.

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15

Sahu, Saugata, Minati Das, Aditya Kumar Bharti, and G. Krishnamoorthy. "Proton transfer triggered proton transfer: a self-assisted twin excited state intramolecular proton transfer." Physical Chemistry Chemical Physics 20, no. 42 (2018): 27131–39. http://dx.doi.org/10.1039/c8cp03835j.

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16

Kerdpol, Khanittha, Rathawat Daengngern, Chanchai Sattayanon, Supawadee Namuangruk, Thanyada Rungrotmongkol, Peter Wolschann, Nawee Kungwan, and Supot Hannongbua. "Effect of Water Microsolvation on the Excited-State Proton Transfer of 3-Hydroxyflavone Enclosed in γ-Cyclodextrin." Molecules 26, no. 4 (February 5, 2021): 843. http://dx.doi.org/10.3390/molecules26040843.

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The effect of microsolvation on excited-state proton transfer (ESPT) reaction of 3-hydroxyflavone (3HF) and its inclusion complex with γ-cyclodextrin (γ-CD) was studied using computational approaches. From molecular dynamics simulations, two possible inclusion complexes formed by the chromone ring (C-ring, Form I) and the phenyl ring (P-ring, Form II) of 3HF insertion to γ-CD were observed. Form II is likely more stable because of lower fluctuation of 3HF inside the hydrophobic cavity and lower water accessibility to the encapsulated 3HF. Next, the conformation analysis of these models in the ground (S0) and the first excited (S1) states was carried out by density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations, respectively, to reveal the photophysical properties of 3HF influenced by the γ-CD. The results show that the intermolecular hydrogen bonding (interHB) between 3HF and γ-CD, and intramolecular hydrogen bonding (intraHB) within 3HF are strengthened in the S1 state confirmed by the shorter interHB and intraHB distances and the red-shift of O–H vibrational modes involving in the ESPT process. The simulated absorption and emission spectra are in good agreement with the experimental data. Significantly, in the S1 state, the keto form of 3HF is stabilized by γ-CD, explaining the increased quantum yield of keto emission of 3HF when complexing with γ-CD in the experiment. In the other word, ESPT of 3HF is more favorable in the γ-CD hydrophobic cavity than in aqueous solution.

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17

Tang, Longteng, Liangdong Zhu, Miles Taylor, Yanli Wang, S. Remington, and Chong Fang. "Excited State Structural Evolution of a GFP Single-Site Mutant Tracked by Tunable Femtosecond-Stimulated Raman Spectroscopy." Molecules 23, no. 9 (September 1, 2018): 2226. http://dx.doi.org/10.3390/molecules23092226.

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Tracking vibrational motions during a photochemical or photophysical process has gained momentum, due to its sensitivity to the progression of reaction and change of environment. In this work, we implemented an advanced ultrafast vibrational technique, femtosecond-stimulated Raman spectroscopy (FSRS), to monitor the excited state structural evolution of an engineered green fluorescent protein (GFP) single-site mutant S205V. This mutation alters the original excited state proton transfer (ESPT) chain. By strategically tuning the Raman pump to different wavelengths (i.e., 801, 539, and 504 nm) to achieve pre-resonance with transient excited state electronic bands, the characteristic Raman modes of the excited protonated (A*) chromophore species and intermediate deprotonated (I*) species can be selectively monitored. The inhomogeneous distribution/population of A* species go through ESPT with a similar ~300 ps time constant, confirming that bridging a water molecule to protein residue T203 in the ESPT chain is the rate-limiting step. Some A* species undergo vibrational cooling through high-frequency motions on the ~190 ps time scale. At early times, a portion of the largely protonated A* species could also undergo vibrational cooling or return to the ground state with a ~80 ps time constant. On the photoproduct side, a ~1330 cm−1 delocalized motion is observed, with dispersive line shapes in both the Stokes and anti-Stokes FSRS with a pre-resonance Raman pump, which indicates strong vibronic coupling, as the mode could facilitate the I* species to reach a relatively stable state (e.g., the main fluorescent state) after conversion from A*. Our findings disentangle the contributions of various vibrational motions active during the ESPT reaction, and offer new structural dynamics insights into the fluorescence mechanisms of engineered GFPs and other analogous autofluorescent proteins.

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18

Hu, Shanshan, Kun Liu, Yuanzuo Li, Qianqian Ding, Wei Peng, and Maodu Chen. "Investigation of excited-state intramolecular proton transfer coupled charge transfer reaction of paeonol." Canadian Journal of Chemistry 92, no. 4 (April 2014): 274–78. http://dx.doi.org/10.1139/cjc-2013-0286.

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An excited-state intramolecular proton transfer (ESIPT) coupled charge transfer reaction of paeonol was investigated both experimentally and theoretically. The ESIPT reaction of paeonol was predicted based on the large Stokes shift, which is observed in steady-state absorption and fluorescence spectra in an ethanol solution. The steady-state spectra in some solutions, such as methanol, ethanol, propanol, dichloromethane, and n-hexane, illustrate that the ESIPT reaction of paeonol has no dependence on the solvent properties. Therefore, the excited-state intermolecular proton transfer cannot be generated in protic solvents. Using the density functional theory and time-dependent density functional theory methods, we make a subsequent theoretical calculation that indicates that the ESIPT reaction of paeonol occurs through the intramolecular hydrogen bond O−H···O=C. The excited-state potential energy curve of paeonol indicates that the ESIPT reaction is a barrierless process, and the fluorescence emission of paeonol at 493 nm in the ethanol solution was assigned to the keto isomer fluorescence. Additionally, we also found an intramolecular charge transfer in the excited state by analysing the frontier molecular orbitals of paeonol.

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19

Nelson, Kacie J., Paige J. Brown, Holly E. Rudel, and Kana Takematsu. "Divergent excited state proton transfer reactions of bifunctional photoacids 1-ammonium-2-naphthol and 3-ammonium-2-naphthol in water and methanol." Physical Chemistry Chemical Physics 21, no. 44 (2019): 24383–92. http://dx.doi.org/10.1039/c9cp05269k.

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20

Liu, Lei, and Bingqing Sun. "pH-related fluorescence quenching mechanism of pterin derivatives and the effects of 6-site substituents." Canadian Journal of Chemistry 96, no. 4 (April 2018): 404–10. http://dx.doi.org/10.1139/cjc-2017-0644.

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2-Amino-4-hydroxypteridine (pterin) and its derivatives serve as photooxidants and exhibit strong fluorescence. When they interact with hydrogen acceptors such as acetate and phosphate, their fluorescences are significantly quenched in acidic conditions (pH 4.9–5.5) but are retained in basic conditions (pH 10.0–10.5). This pH-related fluorescence quenching mechanism of pterin and its derivatives are fully investigated by using density functional theory (DFT) and time-dependent density functional theory (TD-DFT). Pterin and its derivatives are demonstrated to show favorable excited-state proton transfer (ESPT) abilities in acidic conditions that induce the experimentally observed fluorescence quenching. In contrast, the ESPT processes are found to be retarded due to the lack of strong hydrogen-bonding interactions in basic environments, which sustain their fluorescence. Interestingly, these ESPT processes are found to show different site specificities depending on the 6-site substituents. The introduction of electron-donating substituent activates the N1 site, making it the preferred ESPT site. By contrast, the introduction of an electron-withdrawing substituent activates the N5 site, making it the favorable ESPT site. The substitutions of different functional groups are found to affect the locations of acidic centers during the excitation and relaxation processes. This further affects the hydrogen-bonding patterns and ultimately brings site specificity to the ESPT process.

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21

Quina, Frank H., Paulo F. Moreira, Carolina Vautier-Giongo, Daniel Rettori, Rita F. Rodrigues, Adilson A. Freitas, Palmira F. Silva, and António L. Maçanita. "Photochemistry of anthocyanins and their biological role in plant tissues." Pure and Applied Chemistry 81, no. 9 (August 19, 2009): 1687–94. http://dx.doi.org/10.1351/pac-con-08-09-28.

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Anthocyanins, the major red, purple, and blue pigments of plants, absorb visible as well as UV radiation and are effective antioxidants and scavengers of active oxygen species. In plant leaves, one of the functional roles proposed for anthocyanins is protection of the photosynthetic apparatus from the effects of excess incident visible or UV-B radiation and photooxidative stress. In essence, a photoprotective role requires that the excited singlet states of both complexed and uncomplexed anthocyanins deactivate back to the ground state so quickly that intersystem crossing, photoreaction, and diffusion-controlled quenching processes cannot compete. Studies of the photochemical properties of synthetic analogs of anthocyanins and of several naturally occurring anthocyanins show that this is indeed the case, uncomplexed anthocyanins decaying back to the ground state via fast (subnanosecond) excited-state proton transfer (ESPT) and anthocyanin-copigment complexes by fast (subpicosecond) charge-transfer-mediated internal conversion.

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22

Bailey-Darland, Sullivan, Taylor D. Krueger, and Chong Fang. "Ultrafast Spectroscopies of Nitrophenols and Nitrophenolates in Solution: From Electronic Dynamics and Vibrational Structures to Photochemical and Environmental Implications." Molecules 28, no. 2 (January 6, 2023): 601. http://dx.doi.org/10.3390/molecules28020601.

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Nitrophenols are a group of small organic molecules with significant environmental implications from the atmosphere to waterways. In this work, we investigate a series of nitrophenols and nitrophenolates, with the contrasting ortho-, meta-, and para-substituted nitro group to the phenolic hydroxy or phenolate oxygen site (2/3/4NP or NP−), implementing a suite of steady-state and time-resolved spectroscopic techniques that include UV/Visible spectroscopy, femtosecond transient absorption (fs-TA) spectroscopy with probe-dependent and global analysis, and femtosecond stimulated Raman spectroscopy (FSRS), aided by quantum calculations. The excitation-dependent (400 and 267 nm) electronic dynamics in water and methanol, for six protonated or deprotonated nitrophenol molecules (three regioisomers in each set), enable a systematic investigation of the excited-state dynamics of these functional “nanomachines” that can undergo nitro-group twisting (as a rotor), excited-state intramolecular or intermolecular proton transfer (donor–acceptor, ESIPT, or ESPT), solvation, and cooling (chromophore) events on molecular timescales. In particular, the meta-substituted compound 3NP or 3NP− exhibits the strongest charge-transfer character with FSRS signatures (e.g., C–N peak frequency), and thus, does not favor nitroaromatic twist in the excited state, while the ortho-substituted compound 2NP can undergo ESIPT in water and likely generate nitrous acid (HONO) after 267 nm excitation. The delineated mechanistic insights into the nitro-substituent-location-, protonation-, solvent-, and excitation-wavelength-dependent effects on nitrophenols, in conjunction with the ultraviolet-light-induced degradation of 2NP in water, substantiates an appealing discovery loop to characterize and engineer functional molecules for environmental applications.

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23

Basari?, Nikola, and Peter Wan. "Excited state proton transfer (ESPT) from phenol to nitrogen and carbon in (2-hydroxyphenyl)pyridines." Photochemical & Photobiological Sciences 5, no. 7 (2006): 656. http://dx.doi.org/10.1039/b600826g.

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24

Tseng, Huan-Wei, Jiun-Yi Shen, Ting-Yi Kuo, Ting-Syun Tu, Yi-An Chen, Alexander P. Demchenko, and Pi-Tai Chou. "Excited-state intramolecular proton-transfer reaction demonstrating anti-Kasha behavior." Chemical Science 7, no. 1 (2016): 655–65. http://dx.doi.org/10.1039/c5sc01945a.

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When excited with high energy quanta, specially designed 3-hydroxychromone derivatives demonstrate dramatic enhancement of the excited-state intramolecular proton transfer (ESIPT) reaction in obvious violation of Kasha's rule.

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LI, YUANZUO, SHASHA LIU, LILI ZHAO, MAODU CHEN, FENGCAI MA, and YONG DING. "EXCITED-STATE INTRAMOLECULAR ELECTRON TRANSFER COUPLED WITH EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER IN PHOTOINDUCED ENOL TO KETO TAUTOMERIZATION." Journal of Theoretical and Computational Chemistry 08, supp01 (January 2009): 1073–86. http://dx.doi.org/10.1142/s0219633609005246.

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In this paper, the two-dimensional (2D) site and the three-dimensional (3D) cube representations [Sun MT, J Chem Phys124: 054903, 2006] have been further developed to study the charge transfer during excited-state relaxation. With these newly developed representations, we theoretically investigate the excited-state intramolecular electron transfer (ESIET) in enol excited-state geometry relaxation, and ESIET coupled with excited-state intramolecular proton transfer (ESIPT) in phototautomerization (in enol to keto transformation). The energy levels of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of HBODC in enol and keto absorption and fluorescence are compared to understand photoinduced ESIET and ESIPT process. The excited regions of molecule (where arrangement of electron density takes place during excited-state relaxation) are located with 2D site representation. 3D cube representations visualize the character of charge transfer (CT) in those regions. Results of the research indicate that the ability of charge transfer during enol excited-state geometry relaxation is much stronger than that in phototautomerization.

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Liu, Xiumin, Heyao Yuan, Yuxi Wang, Yaping Tao, Yi Wang, and Yingmin Hou. "Theoretical Investigation of Excited-State Intramolecular Double-Proton Transfer Mechanism of Substituent Modified 1, 3-Bis (2-Pyridylimino)-4,7-Dihydroxyisoindole in Dichloromethane Solution." Journal of Computational Biophysics and Chemistry 20, no. 07 (October 13, 2021): 707–18. http://dx.doi.org/10.1142/s2737416521500423.

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In this paper, density functional theory (DFT) and time-dependent DFT (TDDFT) methods were used to investigate substituent effects and excited-state intramolecular double-proton transfer (ESIDPT) in 1, 3-bis (2-pyridylimino)-4, 7-dihydroxyisoindole (BPI–OH) and its derivatives. The results of a systematic study of the substituent effects of electron-withdrawing groups (F, Cl and Br) on the adjacent sites of the benzene ring were used to regulate the photophysical properties of the molecules and the dynamics of the proton-transfer process. Geometric structure comparisons and infrared (IR) spectroscopic analysis confirmed that strengthening of the intramolecular hydrogen bond in the first excited state (S1) facilitated proton transfer. Functional analysis of the reduced density gradient confirmed these conclusions. Double-proton transfer in BPI–OH is considered to occur in two steps, i.e., BPI–OH (N) [Formula: see text] BPI–OH (T1) [Formula: see text] BPI–OH (T2), in the ground state (S0) and the S1 state. The potential-energy curves (PECs) for two-step proton transfer were scanned for both the S0 and S1 states to clarify the mechanisms and pathways of proton transfer. The stepwise path in which two protons are consecutively transferred has a low energy barrier and is more rational and favorable. This study shows that the presence or absence of coordinating groups, and the type of coordinating group, affect the hydrogen-bond strength. A coordinating group enhances hydrogen-bond formation, i.e., it promotes excited-state intramolecular proton transfer (ESIPT).

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Padalkar, Vikas S., and Shu Seki. "Excited-state intramolecular proton-transfer (ESIPT)-inspired solid state emitters." Chemical Society Reviews 45, no. 1 (2016): 169–202. http://dx.doi.org/10.1039/c5cs00543d.

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Dommett, Michael, and Rachel Crespo-Otero. "Excited state proton transfer in 2′-hydroxychalcone derivatives." Physical Chemistry Chemical Physics 19, no. 3 (2017): 2409–16. http://dx.doi.org/10.1039/c6cp07541j.

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ESIPT-active solid-state emitters based on 2-hydroxychalcone are almost non-emissive in solution but emit in the deep red/NIR region when crystalline. A comprehensive theoretical investigation of the gas-phase excited state relaxation pathways in five 2-hydroxychalcone systems is presented, using a combination of static and non-adiabatic simulations.

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29

Consuelo Jiménez, M., Miguel A. Miranda, and Rosa Tormos. "Photocyclization of 2-cinnamylphenols via excited state proton transfer (ESPT) involving the lowest-lying styrenic singlet." Tetrahedron 53, no. 43 (October 1997): 14729–36. http://dx.doi.org/10.1016/s0040-4020(97)00942-3.

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30

Puente-Muñoz, Virginia, Jose M. Paredes, Sandra Resa, Ana M. Ortuño, Eva M. Talavera, Delia Miguel, Juan M. Cuerva, and Luis Crovetto. "Efficient acetate sensor in biological media based on a selective Excited State Proton Transfer (ESPT) reaction." Sensors and Actuators B: Chemical 250 (October 2017): 623–28. http://dx.doi.org/10.1016/j.snb.2017.04.191.

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Liu, Zong-Ying, Jiun-Wei Hu, Teng-Hsing Huang, Kew-Yu Chen, and Pi-Tai Chou. "Excited-state intramolecular proton transfer in the kinetic-control regime." Physical Chemistry Chemical Physics 22, no. 39 (2020): 22271–78. http://dx.doi.org/10.1039/d0cp03408h.

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A new series of ESIPT molecules has been investigated. We found that these compounds undergo kinetic-control ESIPT and the reaction barriers along proton transfer coordinate can be finetuned by different substitution on amino group.

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32

Gajst, Oren, Georgi Gary Rozenman, and Dan Huppert. "Anomalous Rate of H+ and D+ Excited-State Proton Transfer (ESPT) in H2O/D2O Mixtures: Irreversible ESPT in 1-Naphthol-4-sulfonate." Journal of Physical Chemistry A 122, no. 1 (December 19, 2017): 209–16. http://dx.doi.org/10.1021/acs.jpca.7b10684.

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33

Yuan, Huijuan, Xugeng Guo, and Jinglai Zhang. "Ab initio insights into the mechanism of excited-state intramolecular proton transfer triggered by the second excited singlet state of a fluorescent dye: an anti-Kasha behavior." Materials Chemistry Frontiers 3, no. 6 (2019): 1225–30. http://dx.doi.org/10.1039/c9qm00179d.

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An excited-state intramolecular proton transfer (ESIPT) reaction triggered by the second excited singlet S₂ state is found by ab initio calculations to be an ultrafast process for a novel fluorophore.

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34

Wang, Yu-Hsuan, and Peter Wan. "Excited state intramolecular proton transfer (ESIPT) in dihydroxyphenyl anthracenes." Photochemical & Photobiological Sciences 10, no. 12 (2011): 1934. http://dx.doi.org/10.1039/c1pp05187c.

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35

Fan, Ka Wa, Hoi Ling Luk, and David Lee Phillips. "Anti-Kasha Behavior of 3-Hydroxyflavone and Its Derivatives." International Journal of Molecular Sciences 22, no. 20 (October 14, 2021): 11103. http://dx.doi.org/10.3390/ijms222011103.

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Excited state intramolecular proton transfer (ESIPT) in 3-hydroxyflavone (3HF) has been known for its dependence on excitation wavelength. Such a behavior violates Kasha’s rule, which states that the emission and photochemistry of a compound would only take place from its lowest excited state. The photochemistry of 3HF was studied using femtosecond transient absorption spectroscopy at a shorter wavelength excitation (266 nm), and these new experimental findings were interpreted with the aid of computational studies. These new results were compared with those from previous studies that were obtained with a longer wavelength excitation and show that there exists a pathway of proton transfer that bypasses the normal first excited state from the higher excited state to the tautomer from first excited state. The experimental data correlate with the electron density difference calculations such that the proton transfer process is faster on the longer excitation wavelength than compared to the shorter excitation wavelength.

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36

Wang, Ye, Hui Li, and Ying Shi. "Evidence for hydrogen-bonded ammonia wire influencing the ESMPT process of the 7-hydroxy-4-methylcoumarin·(NH3)3 cluster." New Journal of Chemistry 39, no. 9 (2015): 7026–32. http://dx.doi.org/10.1039/c5nj01079a.

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The different types of excited-state hydrogen-bonded dynamics mechanisms orderly provide two driving forces for the excited-state multiple proton transfer (ESMPT) reaction of the 7H4MC·(NH₃)₃ cluster.

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Göbel, Dominik, Daniel Duvinage, Tim Stauch, and Boris J. Nachtsheim. "Nitrile-substituted 2-(oxazolinyl)-phenols: minimalistic excited-state intramolecular proton transfer (ESIPT)-based fluorophores." Journal of Materials Chemistry C 8, no. 27 (2020): 9213–25. http://dx.doi.org/10.1039/d0tc00776e.

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38

Bursulaya, B. D., S. I. Druzhinin, and B. M. Uzhinov. "Fast dynamic excited state proton transfer (ESPT) reaction of weak oxoaromatic bases. Aminocoumarins with fixed amino group." Journal of Photochemistry and Photobiology A: Chemistry 92, no. 3 (December 1995): 163–72. http://dx.doi.org/10.1016/1010-6030(95)04130-x.

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39

Huang, Fuhua, Beibei An, Yumiao Jiang, Shuopan Dun, Jinglai Zhang, and Xugeng Guo. "Theoretical investigation of excited-state proton transfer (ESPT) for 2,5-bis(2-benzothiazolyl)hydroquinone: single or double?" Molecular Physics 118, no. 14 (December 22, 2019): e1705413. http://dx.doi.org/10.1080/00268976.2019.1705413.

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40

Solaris, Janak, Taylor D. Krueger, Cheng Chen, and Chong Fang. "Photogrammetry of Ultrafast Excited-State Intramolecular Proton Transfer Pathways in the Fungal Pigment Draconin Red." Molecules 28, no. 8 (April 16, 2023): 3506. http://dx.doi.org/10.3390/molecules28083506.

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Proton transfer processes of organic molecules are key to charge transport and photoprotection in biological systems. Among them, excited-state intramolecular proton transfer (ESIPT) reactions are characterized by quick and efficient charge transfer within a molecule, resulting in ultrafast proton motions. The ESIPT-facilitated interconversion between two tautomers (PS and PA) comprising the tree fungal pigment Draconin Red in solution was investigated using a combination of targeted femtosecond transient absorption (fs-TA) and excited-state femtosecond stimulated Raman spectroscopy (ES-FSRS) measurements. Transient intensity (population and polarizability) and frequency (structural and cooling) dynamics of –COH rocking and –C=C, –C=O stretching modes following directed stimulation of each tautomer elucidate the excitation-dependent relaxation pathways, particularly the bidirectional ESIPT progression out of the Franck–Condon region to the lower-lying excited state, of the intrinsically heterogeneous chromophore in dichloromethane solvent. A characteristic overall excited-state PS-to-PA transition on the picosecond timescale leads to a unique “W”-shaped excited-state Raman intensity pattern due to dynamic resonance enhancement with the Raman pump–probe pulse pair. The ability to utilize quantum mechanics calculations in conjunction with steady-state electronic absorption and emission spectra to induce disparate excited-state populations in an inhomogeneous mixture of similar tautomers has broad implications for the modeling of potential energy surfaces and delineation of reaction mechanisms in naturally occurring chromophores. Such fundamental insights afforded by in-depth analysis of ultrafast spectroscopic datasets are also beneficial for future development of sustainable materials and optoelectronics.

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Reszka, Milena, Illia E. Serdiuk, Karol Kozakiewicz, Andrzej Nowacki, Henryk Myszka, Piotr Bojarski, and Beata Liberek. "Influence of a 4′-substituent on the efficiency of flavonol-based fluorescent indicators of β-glycosidase activity." Organic & Biomolecular Chemistry 18, no. 38 (2020): 7635–48. http://dx.doi.org/10.1039/d0ob01505a.

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42

Zhu, Hanming, Pan Ma, You Qian, Jiaoyun Xia, Fuchun Gong, Lusen Chen, and Lujie Xu. "Spectral Properties Echoing the Tautomerism of Milrinone and Its Application to Fe3+ Ion Sensing and Protein Staining." Biosensors 12, no. 10 (September 20, 2022): 777. http://dx.doi.org/10.3390/bios12100777.

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Knowledge on the spectral properties of the tautomers of milrinone (MLR) in solvents and solid-state, as well as under light conditions is of critical importance from both theoretical and practical points of view. Herein, we investigated the spectral properties of MLR in different conditions using UV-Vis and fluorescence spectroscopies. The experimental results demonstrated that MLR can undergo the tautomerization reaction induced by solvent polarity, light and pH, eliciting four tautomeric structures (enol, keto, anion, and cation forms). The interesting multi-functional groups in MLR enable it to coordinate with metal ions or to recognize gust molecules by H-bonding. In the use of MLR as an excited-state intermolecular proton transfer (inter-ESPT) fluorescent probe, a highly sensitive and selective analysis of Fe3+ was developed, which offered a sensitive detection of Fe3+ with the detection limit of 3.5 nM. More importantly, MLR exhibited the ability of anchoring proteins and led to the recognition-driven turn-on inter-ESPT process, highlighting the potential for the probe to image proteins in electrophoresis gels. The spectral experimental results revealed the possible degradation mechanism, so that we can better understand the side effects of oral preparations. The use of the available drug as an inter-ESPT fluorescent probe is simple and accurate, providing a good method for Fe3+ ion sensing and protein staining.

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Sreedevi, K. C. Gowri, Ajesh P. Thomas, K. H. Aparna, Renuka Pradhan, M. L. P. Reddy, U. Lourderaj, and A. Srinivasan. "Photoenolization via excited state double proton transfer induces “turn on” fluorescence in diformyl diaryl dipyrromethane." Chem. Commun. 50, no. 63 (2014): 8667–69. http://dx.doi.org/10.1039/c4cc03668a.

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44

Göbel, Dominik, Pascal Rusch, Daniel Duvinage, Nadja C. Bigall, and Boris J. Nachtsheim. "Emission color-tunable oxazol(in)yl-substituted excited-state intramolecular proton transfer (ESIPT)-based luminophores." Chemical Communications 56, no. 98 (2020): 15430–33. http://dx.doi.org/10.1039/d0cc05780k.

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45

Budzák, Šimon, and Denis Jacquemin. "Excited state intramolecular proton transfer in julolidine derivatives: an ab initio study." Physical Chemistry Chemical Physics 20, no. 38 (2018): 25031–38. http://dx.doi.org/10.1039/c8cp04356f.

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We have studied, using ab initio tools, a series of fluorescent julolidine derivatives, undergoing Excited State Intramolecular Proton Transfer (ESIPT) and some unexpected substitution effects have been found.

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46

Han, Jianhui, Xiaochun Liu, Chaofan Sun, You Li, Hang Yin, and Ying Shi. "Ingenious modification of molecular structure effectively regulates excited-state intramolecular proton and charge transfer: a theoretical study based on 3-hydroxyflavone." RSC Advances 8, no. 52 (2018): 29589–97. http://dx.doi.org/10.1039/c8ra05812a.

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Harnessing ingenious modification of molecular structure to regulate excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) characteristics holds great promise in fluorescence sensing and imaging.

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47

Jiang, Guanyu, Feiyan Li, Jianzhong Fan, Yuzhi Song, Chuan-Kui Wang, and Lili Lin. "Theoretical perspective for luminescent mechanism of thermally activated delayed fluorescence emitter with excited-state intramolecular proton transfer." Journal of Materials Chemistry C 8, no. 1 (2020): 98–108. http://dx.doi.org/10.1039/c9tc05299b.

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Matsumoto, Hisato, Yoshinobu Nishimura, and Tatsuo Arai. "Excited-state intermolecular proton transfer dependent on the substitution pattern of anthracene–diurea compounds involved in fluorescent ON1–OFF–ON2 response by the addition of acetate ions." Organic & Biomolecular Chemistry 15, no. 31 (2017): 6575–83. http://dx.doi.org/10.1039/c7ob01376k.

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Qin, Xiaoling, Guoqiang Zhou, Pan Ma, Jiaoyun Xia, Fuchun Gong, Lusen Chen, and Lujie Xu. "A polystyrene-based ESIPT fluorescent polymeric probe for highly sensitive detection of chromium(vi) ions and protein staining." RSC Advances 13, no. 36 (2023): 25350–59. http://dx.doi.org/10.1039/d3ra02698a.

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Zou, Wu, Qinge Wang, Fuchun Gong, Yinjie Kuang, Jiaoyun Xia, and Zhong Cao. "Polymer nanoparticles integrated with ESIPT modules for sensing cysteine based on modulation of their tautomeric emission." Analytical Methods 11, no. 29 (2019): 3714–20. http://dx.doi.org/10.1039/c9ay00888h.

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