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Journal articles on the topic 'Imine switch'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Cordier, Astrid, Pierre-Alain Breuil, Typhène Michel, et al. "Titanium-based phenoxy-imine catalyst for selective ethylene trimerization: effect of temperature on the activity, selectivity and properties of polymeric side products." Catalysis Science & Technology 10, no. 6 (2020): 1602–8. http://dx.doi.org/10.1039/c9cy02056j.

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2

Huber, John D., and James L. Leighton. "Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch." Journal of the American Chemical Society 129, no. 47 (2007): 14552–53. http://dx.doi.org/10.1021/ja076035h.

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3

Berbasova, Tetyana, Elizabeth M. Santos, Meisam Nosrati, Chrysoula Vasileiou, James H. Geiger, and Babak Borhan. "Light-Activated Reversible Imine Isomerization: Towards a Photochromic Protein Switch." ChemBioChem 17, no. 5 (2016): 407–14. http://dx.doi.org/10.1002/cbic.201500613.

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4

Pollok, Corina H., Tim Riesebeck, and Christian Merten. "Photoisomerization of a Chiral Imine Molecular Switch Followed by Matrix-Isolation VCD Spectroscopy." Angewandte Chemie International Edition 56, no. 7 (2017): 1925–28. http://dx.doi.org/10.1002/anie.201610918.

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5

Bei-bei, Liu, Lu Wei, Du Gan-hong, et al. "DESIGN OF AN OPTICALLY ACTIVE POLYSTYRENE BEARING IMINE PENDANTS AND ITS ACID/BASE-TRIGGERED CHIROPTICAL SWITCH PROPERTY." Acta Polymerica Sinica 013, no. 4 (2013): 436–42. http://dx.doi.org/10.3724/sp.j.1105.2013.13007.

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6

Ananikov, Valentin P., Robert Szilagyi, Keiji Morokuma, and Djamaladdin G. Musaev. "Can Steric Effects Induce the Mechanism Switch in the Rhodium-Catalyzed Imine Boration Reaction? A Density Functional and ONIOM Study." Organometallics 24, no. 8 (2005): 1938–46. http://dx.doi.org/10.1021/om049156o.

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7

Volpe, Chiara, Sara Meninno, Angelo Roselli, Michele Mancinelli, Andrea Mazzanti, and Alessandra Lattanzi. "Nitrone/Imine Selectivity Switch in Base‐Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study." Advanced Synthesis & Catalysis 362, no. 23 (2020): 5457–66. http://dx.doi.org/10.1002/adsc.202000855.

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8

Li, Yingguang, Sensen Shang, Lianyue Wang, Ying Lv, Jingyang Niu, and Shuang Gao. "Selectivity-tunable amine aerobic oxidation catalysed by metal-free N,O-doped carbons." Chemical Communications 55, no. 81 (2019): 12251–54. http://dx.doi.org/10.1039/c9cc06793k.

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9

Gong, Qianqian, Yazhen Li, and Fengyi Liu. "Trajectory surface-hopping dynamics of light-driven imine switches." Chemical Physics Letters 751 (July 2020): 137506. http://dx.doi.org/10.1016/j.cplett.2020.137506.

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10

Mahapatra, Ajit Kumar, Syed Samim Ali, Kalipada Maiti, et al. "Aminomethylpyrene-based imino-phenols as primary fluorescence switch-on sensors for Al3+ in solution and in Vero cells and their complexes as secondary recognition ensembles toward pyrophosphate." RSC Advances 5, no. 99 (2015): 81203–11. http://dx.doi.org/10.1039/c5ra16641a.

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11

van Mourik, Tanja, and Herbert Früchtl. "Towards a symmetric reversible single-molecule switch: Amino-imino-cyclo-n-enes." Chemical Physics Impact 3 (December 2021): 100035. http://dx.doi.org/10.1016/j.chphi.2021.100035.

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12

Atay, Ergun, Iva B. Blagoeva, Francis L. Chubb, John T. Edward, Ivan G. Pojarlieff, and Maria M. Toteva. "Assisted hydrolysis of cis-2-(3-phenylthioureido)cyclo pentane-carbonitrile in alkaline solution. Solvent dependent switch from hydrolysis to rearrangement of the iminothiooxopyrimidine intermediate." Canadian Journal of Chemistry 78, no. 1 (2000): 84–94. http://dx.doi.org/10.1139/v99-216.

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The cis and trans isomers of 2-(3-phenylthioureido)cyclopentanecarbonitrile, 1, and the respective carboxamides, 3, and acids, 4, have been prepared. Acid cyclization of both nitriles, faster with the cis isomer, gave the more stable cis-2-thiooxo-cyclopenta[d]pyrimidin-4-one, 7. In base cis-1 formed the cis 4-imino-2-thiooxopyrimidine 2 which in aqueous alkali broke down via 3 to the acid 4; while in the presence of 66% acetonitrile 2 rearranged to the 4-phenyliminopyrimidine 5 to give as final product the thioureido acid 6 carrying no phenyl group. The 1H NMR data for imino and phenylimino derivatives 2 and 5 showed strong bias for conformation A with 1-N pseudoaxial in the cyclopentane ring. Spectra of the E andZ isomers of the iminopyrimidine 2 under slow exchange could be recorded in DMSO-d6. The phenylimino tautomer of 5 is observed in CD3OD and in CDCl3 with the E and Z isomers in a 1:1 ratio. In DMSO-d6 the phenylamino tautomer 5a is also detected. The first process in aqueous KOH, the conversion of nitrile cis-1 into the imino intermediate 2, reaches an equilibrium which shifts towards the nitrile at higher alkalinities because of ionization of the phenylthioureido group (Ke = [2]/[1] = 2.43 and pKAH = 12.74). The cyclization of 1 to 2 is first order in [OH-] while the slower breakdown of 2 is pH independent. The latter is 104 times faster than the hydrolysis of acetonitrile evidencing substantial anchimeric assistance. The change in the reaction route towards the rearranged phenyliminopyrimidine 5 upon addition of acetonitrile can be caused by the lower dielectric constant favouring the elimination step leading to the intermediate isothiocyanate, and by increased activity of OH- accelerating the (presumably) second order elimination step as opposed to the pH-independent hydrolysis of the imino derivative 2. Key words: anchimeric assistance, phenylthioureido nitriles, iminothiooxopyrimidine tautomers, alkaline hydrolysis, solvent effects.

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13

Yang, Zhanhui, Siqi Li, Zhong Zhang, and Jiaxi Xu. "Base-switched annuloselectivity in the reactions of ethyl malonyl chloride and imines." Org. Biomol. Chem. 12, no. 48 (2014): 9822–30. http://dx.doi.org/10.1039/c4ob01454e.

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The [2 + 2] and [2 + 2 + 2] annuloselectivity in the reactions of ethyl malonyl chloride with imines was controlled by different bases, providing a simple synthesis of β-lactam-3-carboxylates and 2,3-dihydro-1,3-oxazin-4-ones.

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14

Bren, Vladimir A., Alexander D. Dubonosov, Oksana S. Popova, Yurii V. Revinskii, Karina S. Tikhomirova, and Vladimir I. Minkin. "Synthesis and Photo- and Ionochromic and Spectral-Luminescent Properties of 5-Phenylpyrazolidin-3-one Azomethine Imines." International Journal of Photoenergy 2018 (September 23, 2018): 1–7. http://dx.doi.org/10.1155/2018/9746534.

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Photochromic 5-phenylpyrazolidin-3-one-based azomethine imines containing 2-((1H-imidazol-2-yl)methylene) 1, 2-(pyridin-2-ylmethylene) 2, 2-(quinolin-2-ylmethylene) 3, and 2-((8-hydroxyquinolin-2-yl)methylene) 4 substituents were synthesized. All the compounds exist in the ring-opened O forms. Under irradiation with light of 365 nm, compounds 1–4 undergo thermally reversible isomerization into ring-closed bicyclic diaziridine isomers C. Azomethine imines 1–3 exhibit properties of ion-active molecular “off-on” switches of fluorescence when interacting with F− or AcO− anions. Compound 4 represents a bifunctional chemosensor demonstrating a colorimetric “naked-eye” effect for Ni2+ cation and complete fluorescence quenching in the presence of H+, F−, and CN− ions.

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15

Zhang, Kan, Yuqi Liu, Zhikun Shang, Corey Evans, and Shengfu Yang. "Effects of End-Caps on the Atropisomerization, Polymerization, and the Thermal Properties of ortho-Imide Functional Benzoxazines." Polymers 11, no. 3 (2019): 399. http://dx.doi.org/10.3390/polym11030399.

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A new type of atropisomerism has recently been discovered in 1,3-benzoxazines, where the intramolecular repulsion between negatively charged oxygen atoms on the imide and the oxazine ring hinders the rotation about the C–N bond. The imide group offers a high degree of flexibility for functionalization, allowing a variety of functional groups to be attached, and producing different types of end-caps. In this work, the effects of end-caps on the atropisomerism, thermally activated polymerization of ortho-imide functional benzoxazines, and the associated properties of polybenzoxazines have been systematically investigated. Several end-caps, with different electronic characteristics and rigidities, were designed. 1H and 13C nuclear magnetic resonance (NMR) spectroscopy and density functional theory (DFT) calculations were employed to obtain structural information, and differential scanning calorimetry (DSC) and in situ Fourier transform infrared (FT-IR) spectroscopy were also performed to study the thermally activated polymerization process of benzoxazine monomers. We demonstrated that the atropisomerization can be switched on/off by the manipulation of the steric structure of the end-caps, and polymerization behaviors can be well-controlled by the electronic properties of the end-caps. Moreover, a trade-off effect were found between the thermal properties and the rigidity of the end-caps in polybenzoxazines.

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16

Wang, Kun Li, Jian Wei Lee, I. Hao Shih, Yi Liang Liu, and En Tang Kang. "Resistive Polymer Memory Materials Containing Electron Donor and Acceptor Moieties." Advanced Materials Research 488-489 (March 2012): 3–7. http://dx.doi.org/10.4028/www.scientific.net/amr.488-489.3.

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Two series of polymers including polyimides and poly(aryl ether)s were prepared and used as active layers of polymer memories. The poly(aryl ether)-based polymers showed flash behaviors and polyimide-based polymers showed WORM behaviors. The poly(aryl ether)s flash memories can be negatively switched on and positively switched off, and the switching voltages are relative to the chemical structure of bisphenol moiety. On the other hand, the polyimide-based polymer devices can be bidirectionally switched on with comparable positive and negative switching threshold voltages, but cannot be switched off. The polyimides showed write-once-and-read- many-times (WORM) memory behavior. The poly(aryl ether) (AZTA-PAEb) showed very different memory behavior from polyimides (AZTA-PI and AZTA-PEI) although they contain the similar chemical structure (electron-donor triphenylamine and electron-acceptor triazine moieties). The imide structure in the polyimides plays a great role in the memory effects.

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17

Paillares, Eléa, Maud Marechal, Léa Swistak, Landry Tsoumtsa Meda, Emmanuel Lemichez, and Thérèse E. Malliavin. "Conformational Insights into the Control of CNF1 Toxin Activity by Peptidyl-Prolyl Isomerization: A Molecular Dynamics Perspective." International Journal of Molecular Sciences 22, no. 18 (2021): 10129. http://dx.doi.org/10.3390/ijms221810129.

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The cytotoxic necrotizing factor 1 (CNF1) toxin from uropathogenic Escherichia coli constitutively activates Rho GTPases by catalyzing the deamidation of a critical glutamine residue located in the switch II (SWII). In crystallographic structures of the CNF1 catalytic domain (CNF1CD), surface-exposed P768 and P968 peptidyl-prolyl imide bonds (X-Pro) adopt an unusual cis conformation. Here, we show that mutation of each proline residue into glycine abrogates CNF1CD in vitro deamidase activity, while mutant forms of CNF1 remain functional on RhoA in cells. Using molecular dynamics simulations coupled to protein-peptide docking, we highlight the long-distance impact of peptidyl-prolyl cis-trans isomerization on the network of interactions between the loops bordering the entrance of the catalytic cleft. The energetically favorable isomerization of P768 compared with P968, induces an enlargement of loop L1 that fosters the invasion of CNF1CD catalytic cleft by a peptide encompassing SWII of RhoA. The connection of the P968 cis isomer to the catalytic cysteine C866 via a ladder of stacking interactions is alleviated along the cis-trans isomerization. Finally, the cis-trans conversion of P768 favors a switch of the thiol side chain of C866 from a resting to an active orientation. The long-distance impact of peptidyl-prolyl cis-trans isomerizations is expected to have implications for target modification.

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18

Yang, Zhanhui, Siqi Li, Zhong Zhang, and Jiaxi Xu. "ChemInform Abstract: Base-Switched Annuloselectivity in the Reactions of Ethyl Malonyl Chloride and Imines." ChemInform 46, no. 17 (2015): no. http://dx.doi.org/10.1002/chin.201517038.

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19

Hernández-Toribio, Jorge, Ramón Gómez Arrayás та Juan Carlos Carretero. "Substrate-Controlled Diastereoselectivity Switch in Catalytic Asymmetric Direct Mannich Reaction of Glycine Derivatives with Imines: Fromanti- tosyn-α,β-Diamino Acids". Chemistry - A European Journal 16, № 4 (2010): 1153–57. http://dx.doi.org/10.1002/chem.200902258.

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20

Jana, Poulami, Filip Šupljika, Carsten Schmuck, and Ivo Piantanida. "Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator." Beilstein Journal of Organic Chemistry 16 (September 8, 2020): 2201–11. http://dx.doi.org/10.3762/bjoc.16.185.

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A novel naphthalene diimde analogue (NDI) equipped at the imide positions with two guanidinio-carbonyl-pyrrole (GCP) pendant arms interacted significantly stronger with ds-DNA at pH 5 than at pH 7, due to reversible protonation of the GCP arms. This was consequence of a pH-switchable threading intercalation into ds-DNAs only at pH 5, while at neutral conditions (pH 7) NDI-GCP2 switched to the DNA minor groove binding. Intriguingly, NDI-GCP2 was at both pH values studied bound to the ds-RNA major groove, still showing a higher affinity and thermal denaturation effect at pH 5 due to GCP protonation. At excess over the DNA/RNA conjugate NDI-GCP2 showed also aggregation along the ds-polynucleotide and AFM and DLS demonstrated that NDI-GCP2 has pronounced ds-DNA condensation ability.

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21

Hernandez-Toribio, Jorge, Ramon Gomez Arrayas та Juan Carlos Carretero. "ChemInform Abstract: Substrate-Controlled Diastereoselectivity Switch in Catalytic Asymmetric Direct Mannich Reaction of Glycine Derivatives with Imines: From anti- to syn-α,β-Diamino Acids." ChemInform 41, № 22 (2010): no. http://dx.doi.org/10.1002/chin.201022068.

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22

Zhang, Leilei, Wentao Wang, Aiqin Wang, et al. "Aerobic oxidative coupling of alcohols and amines over Au–Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines." Green Chemistry 15, no. 10 (2013): 2680. http://dx.doi.org/10.1039/c3gc41117f.

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23

Wang, Zi-Tian, Yuan Zhao, Zhan-Yong Wang та Ying Cheng. "N-Heterocyclic Carbene-Catalyzed Diastereoselective and Enantioselective Reaction of 2-Aroylvinylcinnamaldehydes with α,β-Unsaturated Imines: Complete Control and Switch of Diastereoselectivity by N-Substituents of Catalysts". Journal of Organic Chemistry 80, № 3 (2015): 1727–34. http://dx.doi.org/10.1021/jo502668c.

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24

Zhang, Tao, and et al et al. "ChemInform Abstract: Aerobic Oxidative Coupling of Alcohols and Amines over Au-Pd/Resin in Water: Au/Pd Molar Ratios Switch the Reaction Pathways to Amides or Imines." ChemInform 45, no. 7 (2014): no. http://dx.doi.org/10.1002/chin.201407079.

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25

Wang, Teng-Hui, Wei-Xiang Wang, and Hai-Chou Chang. "Pressure-Dependent Clustering in Ionic-Liquid-Poly (Vinylidene Fluoride) Mixtures: An Infrared Spectroscopic Study." Nanomaterials 11, no. 8 (2021): 2099. http://dx.doi.org/10.3390/nano11082099.

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The nanostructures of ionic liquids (ILs) have been the focus of considerable research attention in recent years. Nevertheless, the nanoscale structures of ILs in the presence of polymers have not been described in detail at present. In this study, nanostructures of ILs disturbed by poly(vinylidene fluoride) (PVdF) were investigated via high-pressure infrared spectra. For 1-(2-hydroxyethyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([HEMIm][TFSI])-PVdF mixtures, non-monotonic frequency shifts of the C4,5-H vibrations upon dilution were observed under ambient pressure. The experimental results suggest the presence of microheterogeneity in the [HEMIm][TFSI] systems. Upon compression, PVdF further influenced the local structure of C4,5–H via pressure-enhanced IL–PVdF interactions; however, the local structures of C2–H and hydrogen-bonded O–H were not affected by PVdF under high pressures. For choline [TFSI]–PVdF mixtures, PVdF may disturb the local structures of hydrogen-bonded O–H. In the absence of the C4,5–H⋯anion and C2–H⋯anion in choline [TFSI]–PVdF mixtures, the O–H group becomes a favorable moiety for pressure-enhanced IL–PVdF interactions. Our results indicate the potential of high-pressure application for designing pressure-dependent electronic switches based on the possible changes in the microheterogeneity and electrical conductivity in IL-PVdF systems under various pressures.

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26

Wang, Zi-Tian, Yuan Zhao, Zhan-Yong Wang та Ying Cheng. "ChemInform Abstract: N-Heterocyclic Carbene-Catalyzed Diastereoselective and Enantioselective Reaction of 2-Aroylvinylcinnamaldehydes with α,β-Unsaturated Imines: Complete Control and Switch of Diastereoselectivity by N-Substituents of Catalysts." ChemInform 46, № 26 (2015): no. http://dx.doi.org/10.1002/chin.201526175.

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27

Nandi, Leandro G., Felipe Facin, Vanderléia G. Marini, et al. "Nitro-Substituted 4-[(Phenylmethylene)imino]phenolates: Solvatochromism and Their Use as Solvatochromic Switches and as Probes for the Investigation of Preferential Solvation in Solvent Mixtures." Journal of Organic Chemistry 77, no. 23 (2012): 10668–79. http://dx.doi.org/10.1021/jo301890r.

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28

Kumar Pathak, Rakesh, Vijaya Kumar Hinge, Ankit Rai, Dulal Panda, and Chebrolu Pulla Rao. "Imino–Phenolic–Pyridyl Conjugates of Calix[4]arene (L1 and L2) as Primary Fluorescence Switch-on Sensors for Zn2+ in Solution and in HeLa Cells and the Recognition of Pyrophosphate and ATP by [ZnL2]." Inorganic Chemistry 51, no. 9 (2012): 4994–5005. http://dx.doi.org/10.1021/ic202426v.

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29

Kloeber, Jake A., Teresa K. Kimlinger, Jessica L. Haug, Kimberly J. Henderson, S. Vincent Rajkumar, and Shaji K. Kumar. "Immunological Consequences of Lenalidomide with and without Dexamethasone in Newly Diagnosed Multiple Myeloma." Blood 134, Supplement_1 (2019): 3070. http://dx.doi.org/10.1182/blood-2019-128335.

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Introduction: Recent advancements in the treatment of multiple myeloma (MM) have centered on engaging the immune system to target multiple myeloma cells. Although these therapies are being combined with immunomodulatory imide drugs (IMiDs) and corticosteroids, the individual contributions of these drugs on the immune system of MM patients has not been examined in the upfront setting. In this study, we examined the peripheral blood immunophenotypes of newly diagnosed multiple myeloma (NDMM) patients receiving the IMiD lenalidomide with or without the corticosteroid dexamethasone. Methods: To characterize immunophenotypes, we utilized flow cytometry to profile white blood cell populations from 35 patients enrolled in a clinical trial testing the efficacy of lenalidomide with and without dexamethasone in NDMM (NCT00772915). In this trial, all patients were initiated on single-agent lenalidomide. Dexamethasone was initiated in patients that did not meet desirable responses or for disease progression. At each cycle, peripheral blood was stained with a 17-marker antibody panel against several immune lineages and functional surface markers. We grouped patients into two groups: 1) lenalidomide alone or 2) lenalidomide with dexamethasone according to their treatment regimen at each cycle timepoint. Results: First we confirmed anti-myeloma cell activity for both groups by measuring a steady decline in circulating plasma cells in both groups. Examining peripheral blood immunophenotypes showed an expected decrease in T cells and a smaller decrease in B cells in both groups of patients. Closer inspection of B cell populations revealed a switch towards a more immature B cell phenotype in both treatment groups. This was measured as a switch from CD19-CD20+ cells to CD19+CD20- B cells. Inspection of T cell subsets revealed that patients receiving single-agent lenalidomide had a sustained decrease in the levels of CD4+ T cells and increase in the levels of CD8+ T cells. This was seen in both naïve and regulatory T cells evidenced by a decrease in the CD4/CD8 ratio among CD28+ T cells as well as CD25+ T cells. Importantly, this alteration did not lead to sustained alterations in the overall level of CD25+ or CD28+ T cells, and the addition of dexamethasone reverses this trend. In addition to the effects seen on T and B cell numbers, we detected expansions of NK cell populations in patients receiving lenalidomide alone. This expansion is detected as an overall increase in CD56+ mononuclear cells with the majority of cells being CD56+CD3- cells. Conclusions: Our data show that lenalidomide and dexamethasone therapy have shared but distinct effects on peripheral blood immunophenotypes in NDMM. Both drugs alter B cells numbers and populations leading to an expansion of CD19+CD20- B cells. However, lenalidomide alone decreases the CD4/CD8 T cell ratio; and, lenalidomide more strongly expands NK cell populations. The addition of dexamethasone reverses this trend and leads to a restoration of the CD4/CD8 ratio. This suggests that lenalidomide without dexamethasone might be counterproductive in immunotherapies intended to recruit CD4+ T cells. Conversely, lenalidomide alone could increase the efficacy of immunotherapies dependent on NK cell recruitment such as antibody-dependent cellular cytotoxicity (ADCC). This information may benefit future investigations of immune responses in MM patients and improve the adoption of immunotherapies to MM patients. Figure Disclosures Kumar: Celgene: Consultancy, Research Funding; Janssen: Consultancy, Research Funding; Takeda: Research Funding.

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30

Arupula, Sanjeeva K., Asif Ali Qureshi та K. C. Kumara Swamy. "Lewis Base-Switched [3 + 3] and [4 + 2] Annulation Reactions of δ-Acetoxy Allenoates with Cyclic N-Sulfonyl Imines: Divergent Synthesis of Functionalized α-Pyridyl Acetates and Teraryl Scaffolds". Journal of Organic Chemistry 85, № 6 (2020): 4130–44. http://dx.doi.org/10.1021/acs.joc.9b03281.

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31

Huber, John D., and James L. Leighton. "ChemInform Abstract: Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch." ChemInform 39, no. 14 (2008). http://dx.doi.org/10.1002/chin.200814075.

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32

Liu, Changxia, Cuifang Dong, Shuheng Liu, Yang Yang, and Zhichao Zhang. "Multiple Chiroptical Switches and Logic Circuit Based on Salicyl‒ Imine‒Chitosan Hydrogel." Carbohydrate Polymers, December 2020, 117534. http://dx.doi.org/10.1016/j.carbpol.2020.117534.

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33

Voegeli, Wolfgang, Etsuo Arakawa, Tadashi Matsushita, Osami Sakata, and Yusuke Wakabayashi. "Dynamical Response of the Electric Double Layer Structure of the DEME-TFSI Ionic Liquid to Potential Changes Observed by Time-Resolved X-ray Reflectivity." Zeitschrift für Physikalische Chemie 230, no. 4 (2016). http://dx.doi.org/10.1515/zpch-2015-0669.

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AbstractThe interface between the N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide (DEME-TFSI) ionic liquid and a gold (111) surface was investigated with time-resolved X-ray reflectivity in order to clarify the dynamics of structural changes of the electric double layer after changing the electrode potential. In the experiment, the potential was switched repeatedly between +1.5 V and −1.5 V every 2 s or every 0.3 s, while measuring the specular X-ray reflectivity. When the potential was switched every 2 s, the time dependence of the reflectivity was different from that of the accumulated charge. This indicates structural relaxation processes that occur on a slower time scale than the acummulation of the charge at the electric double layer.When the potential was switched every 0.3 s, on the other hand, the reflectivity changes followed the evolution of the charge of the electric double layer within the experimental precision, indicating that slow relaxation processes without charge transfer do not contribute significantly to structural changes at this time scale.

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