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Journal articles on the topic 'Surface chemistry of zwitterion'

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Author: Grafiati

Published: 25 May 2024

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1

Abdullah, Norfadhilatuladha, Norhaniza Yusof, Mohammed Abdullah Dahim, Muhammad Faris Hamid, Lau Woei Jye, Juhana Jaafar, Farhana Aziz, Wan Norhayati Wan Salleh, Ahmad Fauzi Ismail, and Nurasyikin Misdan. "Single-Step Surface Hydrophilization on Ultrafiltration Membrane with Enhanced Antifouling Property for Pome Wastewater Treatment." Separations 10, no. 3 (March 9, 2023): 188. http://dx.doi.org/10.3390/separations10030188.

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High organic materials in palm oil mill effluent (POME) can result in serious water pollution. To date, biological treatment has been used to reduce the environmental risks of these effluents prior of their discharge into water streams. However, the effluents’ dark brownish colour remains as a significant issue that must be addressed, as it affects the overall quality of water. Although membrane technology has been frequently used to address these difficulties, membrane fouling has become a serious limitation in POME treatment. On the other hand, zwitterions with balanced charge groups have received growing interest in the fabrication of antifouling membranes due to their hydrated nature. The development of a simple and efficient covalent bonding technique to improve the stability of zwitterions on membrane surfaces remains a challenge. By grafting and co-depositing polyethylenimine (PEI)-based zwitterion (Z-PEI) with super hydrophilic polydopamine (PDA) on the surface of a commercial polysulfone (PSf) ultrafiltration membrane at ambient temperature, a new zwitterionic surface with a neutral surface charge was created (PDA/Z-PEI). This study aims to investigate the effect of different loading ratios of PDA/Z-PEI (1:1, 1:2, and 1:3) and evaluate their performance on treating brownish coloured anaerobically treated POME (AT-POME). SEM and FTIR analysis showed the successful incorporation of the PDA/Z-PEI membrane while the zwitterionic feature is indicated by zeta potential analysis. Water flux analysis demonstrated that a lower water flux was achieved for M-ZPEI membranes as compared to the PSf and PSf-MDPA membranes, attributed by the tight skin layer of PDA-ZPEI. In the development of a tight hydration layer on the membrane surface by zwitterions, zwitterionic membranes demonstrated excellent antifouling capabilities, particularly PDA/Z-PEI with a loading ratio of (1:2) with a flux recovery ratio of around 84% and colour rejection of 81.75%. Overall, this research contributes to the development of a unique coating with improved stability and antifouling properties by altering the membrane surface in a simple and reliable manner.

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2

Regev, Clil, Zhongyi Jiang, Roni Kasher, and Yifat Miller. "Distinct Antifouling Mechanisms on Different Chain Densities of Zwitterionic Polymers." Molecules 27, no. 21 (October 31, 2022): 7394. http://dx.doi.org/10.3390/molecules27217394.

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Antifouling polymer coating surfaces are used in widespread industries applications. Zwitterionic polymers have been identified as promising materials in developing polymer coating surfaces. Importantly, the density of the polymer chains is crucial for acquiring superior antifouling performance. This study introduces two different zwitterionic polymer density surfaces by applying molecular modeling tools. To assess the antifouling performance, we mimic static adsorption test, by placing the foulant model bovine serum albumin (BSA) on the surfaces. Our findings show that not only the density of the polymer chain affect antifouling performance, but also the initial orientation of the BSA on the surface. Moreover, at a high-density surface, the foulant either detaches from the surface or anchor on the surface. At low-density surface, the foulant does not detach from the surface, but either penetrates or anchors on the surface. The anchoring and the penetrating mechanisms are elucidated by the electrostatic interactions between the foulant and the surface. While the positively charged ammonium groups of the polymer play major role in the interactions with the negatively charged amino acids of the BSA, in the penetrating mechanism the ammonium groups play minor role in the interactions with the contact with the foulant. The sulfonate groups of the polymer pull the foulant in the penetrating mechanism. Our work supports the design of a high-density polymer chain surface coating to prevent fouling phenomenon. Our study provides for the first-time insights into the molecular mechanism by probing the interactions between BSA and the zwitterion surface, while testing high- and low-densities polymer chains.

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3

Chiao, Yu-Hsuan, Arijit Sengupta, Micah Belle Marie Yap Ang, Shu-Ting Chen, Teow Yeit Haan, Jorge Almodovar, Wei-Song Hung, and S. Ranil Wickramasinghe. "Application of Zwitterions in Forward Osmosis: A Short Review." Polymers 13, no. 4 (February 15, 2021): 583. http://dx.doi.org/10.3390/polym13040583.

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Forward osmosis (FO) is an important desalination method to produce potable water. It was also used to treat different wastewater streams, including industrial as well as municipal wastewater. Though FO is environmentally benign, energy intensive, and highly efficient; it still suffers from four types of fouling namely: organic fouling, inorganic scaling, biofouling and colloidal fouling or a combination of these types of fouling. Membrane fouling may require simple shear force and physical cleaning for sufficient recovery of membrane performance. Severe fouling may need chemical cleaning, especially when a slimy biofilm or severe microbial colony is formed. Modification of FO membrane through introducing zwitterionic moieties on the membrane surface has been proven to enhance antifouling property. In addition, it could also significantly improve the separation efficiency and longevity of the membrane. Zwitterion moieties can also incorporate in draw solution as electrolytes in FO process. It could be in a form of a monomer or a polymer. Hence, this review comprehensively discussed several methods of inclusion of zwitterionic moieties in FO membrane. These methods include atom transfer radical polymerization (ATRP); second interfacial polymerization (SIP); coating and in situ formation. Furthermore, an attempt was made to understand the mechanism of improvement in FO performance by zwitterionic moieties. Finally, the future prospective of the application of zwitterions in FO has been discussed.

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4

Li, Bor-Ran, Mo-Yuan Shen, Hsiao-hua Yu, and Yaw-Kuen Li. "Rapid construction of an effective antifouling layer on a Au surface via electrodeposition." Chem. Commun. 50, no. 51 (2014): 6793–96. http://dx.doi.org/10.1039/c4cc01329h.

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5

Penfold, Jeffrey, and Robert K. Thomas. "Neutron reflection and the thermodynamics of the air–water interface." Physical Chemistry Chemical Physics 24, no. 15 (2022): 8553–77. http://dx.doi.org/10.1039/d2cp00053a.

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Neutron reflection measures the surface composition of mixtures and quantifies their interactions. The illustration shows the behaviour of an ionic-zwitterion surfactant mixture and a possible configuration of the molecules at the surface.

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6

Dassonville, Delphine, Thomas Lécuyer, Johanne Seguin, Yohann Corvis, Jianhua Liu, Guanyu Cai, Julia Mouton, Daniel Scherman, Nathalie Mignet, and Cyrille Richard. "Zwitterionic Functionalization of Persistent Luminescence Nanoparticles: Physicochemical Characterizations and In Vivo Biodistribution in Mice." Coatings 13, no. 11 (November 8, 2023): 1913. http://dx.doi.org/10.3390/coatings13111913.

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After excitation in the biological transparency window, chromium-doped zinc gallate nanoparticles (ZGO NPs) emit near-infrared luminescence for more than an hour, allowing long-term imaging to be performed without background autofluorescence. However, these nanoparticles are recognized in just a few minutes by serum proteins and are then trapped in the liver. In this article, we put forth that liver uptake can be delayed when coating the surface of ZGO NPs with zwitterions. We focused on the use of a very small zwitterion molecule of 330 Da derived from sulfobetaine silane (SBS) and its grafting in one step and in water onto zinc gallate nanoparticles, and we compared the colloidal stability, the in vitro interactions with serum proteins, and the biodistribution in mice with PEGylated ZGO NPs (5000 Da) prepared in two steps in organic solvent. In vitro quantification of serum protein adsorption suggests that the similarity between the sulfobetaine and the cell membrane is enough to reduce protein adsorption as much as a PEGylation, despite the difference in coating thickness and molecular weight. This study has also proved that a combination of good protein repulsion and a smaller size compared to PEGylated NPs allows similar circulation times to be obtained in mice with zwitterionic or PEG coatings. Therefore, its use could offer new opportunities for further in vivo application of functionalized ZGO derivative NPs.

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7

Nikam, Shantanu P., Peiru Chen, Karissa Nettleton, Yen-Hao Hsu, and Matthew L. Becker. "Zwitterion Surface-Functionalized Thermoplastic Polyurethane for Antifouling Catheter Applications." Biomacromolecules 21, no. 7 (May 27, 2020): 2714–25. http://dx.doi.org/10.1021/acs.biomac.0c00456.

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8

Mondini, Sara, Marianna Leonzino, Carmelo Drago, Anna M. Ferretti, Sandro Usseglio, Daniela Maggioni, Paolo Tornese, Bice Chini, and Alessandro Ponti. "Zwitterion-Coated Iron Oxide Nanoparticles: Surface Chemistry and Intracellular Uptake by Hepatocarcinoma (HepG2) Cells." Langmuir 31, no. 26 (June 23, 2015): 7381–90. http://dx.doi.org/10.1021/acs.langmuir.5b01496.

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9

Kravchenko, A. A., E. M. Demianenko, A. G. Grebenyuk, M. I. Terets, M. G. Portna, and V. V. Lobanov. "Quantum chemical study on the interaction of arginine with silica surface." Himia, Fizika ta Tehnologia Poverhni 12, no. 4 (December 30, 2021): 358–64. http://dx.doi.org/10.15407/hftp12.04.358.

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The structure and energy characteristics of structures formed during arginine adsorption on silica surface from aqueous solution were studied by the density functional theory (B3LYP) method using a valence-split basis set 6-31++G(d,p) within the continuous solvent model (PCM) and supermolecular approximation. The equilibrium structural and energy parameters of the protonated arginine molecule in the gas phase dependent on the location of the hydrogen atom are considered including those of two possible zwitterions. The structure of the arginine ion Н2А+, which is formed when a proton attaches to a molecule or zwitterion of a given amino acid, has been elucidated. To determine the deprotonation constant of the carboxyl group in an acidic medium, the complexes of the arginine molecule (AH32+) in the state with undissociated and deprotonated carboxyl groups are considered. The simulation of the acid medium was performed by taking into account the interaction with two hydrated HCl ion pairs, which provided the protonation of the a-amino group and the nitrogen atom of amino group within the guanidine group. In the study on the interaction of an arginine molecule with silica surface in an aqueous medium, complexes containing a Si8O12(OH)7O– ion with a deprotonated silanol group, six water molecules, and an arginine molecule with a deprotonated carboxyl group were considered. It has been found that the arginine molecule is most likely to be adsorbed on slica surface with formation of hydrogen bonds between the hydrogen atoms of the a-amino group and the oxygen atom of the deprotonated silanol group. In this case, the formation of a hydrogen bond between the oxygen atom of the carboxyl group and the hydrogen atom of the neighboring silanol group is possible. Slightly less likely is adsorption of arginine molecules due to interaction of the guanidine group with silanol groups of the surface. According to the calculated data, the adsorption of the zwitterionic form of the arginine molecule from the aqueous solution is equally likely to occur due to interaction of silanol groups of silica surface with both the carboxyl group and the guanidine group.

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10

Costa, Paolo, Iris Trosien, Joel Mieres-Perez, and Wolfram Sander. "Isolation of an Antiaromatic Singlet Cyclopentadienyl Zwitterion." Journal of the American Chemical Society 139, no. 37 (September 11, 2017): 13024–30. http://dx.doi.org/10.1021/jacs.7b05807.

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11

Ionkin, Alex S., William J. Marshall, Brian M. Fish, Matthew F. Schiffhauer, and Fredric Davidson. "A Stabilized β-Oxaphosphoniumbetaine: An Elusive Zwitterion." Journal of the American Chemical Society 129, no. 29 (July 2007): 9210–15. http://dx.doi.org/10.1021/ja071644a.

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12

Sun, Ding, Peiyun Li, Xiong Li, and Xuefen Wang. "Protein-resistant surface based on zwitterion-functionalized nanoparticles for marine antifouling applications." New Journal of Chemistry 44, no. 5 (2020): 2059–69. http://dx.doi.org/10.1039/c9nj04266k.

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A functional nanocomposite (PSBMA@VTMO@silica/TA-PEG) coating was successfully developed through a facile deposition method, and was able to effectively block the adhesion of proteins and subsequent biofouling deposition.

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13

Arasawa, Hiroko, Chiharu Odawara, Ruriko Yokoyama, Hiroshi Saitoh, Takeshi Yamauchi, and Norio Tsubokawa. "Grafting of zwitterion-type polymers onto silica gel surface and their properties." Reactive and Functional Polymers 61, no. 2 (September 2004): 153–61. http://dx.doi.org/10.1016/j.reactfunctpolym.2004.04.006.

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14

Dunbar, Robert C., Nick C. Polfer, and Jos Oomens. "Gas-Phase Zwitterion Stabilization by a Metal Dication." Journal of the American Chemical Society 129, no. 47 (November 2007): 14562–63. http://dx.doi.org/10.1021/ja076131i.

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15

Bush, Matthew F., James S. Prell, Richard J. Saykally, and Evan R. Williams. "One Water Molecule Stabilizes the Cationized Arginine Zwitterion." Journal of the American Chemical Society 129, no. 44 (November 2007): 13544–53. http://dx.doi.org/10.1021/ja073796b.

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16

Antoine, Rodolphe, Michel Broyer, Philippe Dugourd, Gary Breaux, Frederick C. Hagemeister, David Pippen, Robert R. Hudgins, and Martin F. Jarrold. "Direct Probing of Zwitterion Formation in Unsolvated Peptides." Journal of the American Chemical Society 125, no. 30 (July 2003): 8996–97. http://dx.doi.org/10.1021/ja035912q.

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17

Lu, Qiuyi, Zhoujie Wang, Shishuang Zhang, Jingyi Wang, Xiaohui Mao, Lei Xie, Qi Liu, and Hongbo Zeng. "Molecular interaction mechanism for humic acids fouling resistance on charged, zwitterion-like and zwitterionic surfaces." Journal of Colloid and Interface Science 666 (July 2024): 393–402. http://dx.doi.org/10.1016/j.jcis.2024.04.038.

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18

Meng, Hong, Qiang Cheng, Haizhi Wang, and Chunxi Li. "Improving Anti-Protein-Fouling Property of Polyacrylonitrile Ultrafiltration Membrane by Grafting Sulfobetaine Zwitterions." Journal of Chemistry 2014 (2014): 1–9. http://dx.doi.org/10.1155/2014/304972.

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Zwitterions show great superiority in the field of polymer membrane surface functionalization, as the synthesis process is simple, the adaptability of functional groups is strong, and zwitterions with strong hydration capacity in aqueous solutions can inhibit protein adsorption. In this study, a polyacrylonitrile ultrafiltration membrane was modified to improve anti-protein-fouling capacity by grafting short-chain sulfonic type zwitterions. 3-Dimethylaminopropylamine was first grafted onto hydrolyzed polyacrylonitrile (PAN) membrane by the activation of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC). Subsequently, sulfobetaine zwitterions emerged on the membrane surface by quaternization of 1,3-propane sultone. The sulfobetaine zwitterionic membranes were analyzed for surface chemical composition, hydrophilic properties, and surface and cross-sectional structure of the membrane, by a combination of Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, contact angle measurement, and scanning electron microscopy. Static protein adsorption and dynamic filtration experiments were undertaken to show that the modified membrane had excellent resistance to protein adsorption. It was found that the molecular weight cutoff of the substrate membrane had great influence on the flux recovery rate of the modified membrane.

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19

Kapitán, Josef, Vladimír Baumruk, Vladimír Kopecký,, Radek Pohl, and Petr Bouř. "Proline Zwitterion Dynamics in Solution, Glass, and Crystalline State." Journal of the American Chemical Society 128, no. 41 (October 2006): 13451–62. http://dx.doi.org/10.1021/ja062958l.

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20

Mizuya, Jiro, Tsutomu Yokozawa, and Takeshi Endo. "Selective alternating copolymerization of allene derivatives through macroallyl zwitterion." Journal of the American Chemical Society 111, no. 2 (January 1989): 743–44. http://dx.doi.org/10.1021/ja00184a059.

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21

Kobayashi, Motoyasu, Yuki Terayama, Moriya Kikuchi, and Atsushi Takahara. "Chain dimensions and surface characterization of superhydrophilic polymer brushes with zwitterion side groups." Soft Matter 9, no. 21 (2013): 5138. http://dx.doi.org/10.1039/c3sm27700c.

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22

Trost, Barry M., and Juan R. Granja. "A carbonyl 1,1-zwitterion synthon for ester and macrolide synthesis." Journal of the American Chemical Society 113, no. 3 (January 1991): 1044–46. http://dx.doi.org/10.1021/ja00003a049.

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23

Vousoughi, Pedram, Mohammad Reza Moghbeli, and Sousa Javan Nikkhah. "Molecular Dynamics (MD) Simulation of Zwitterion-Functionalized PMMA with Hydrophilic and Antifouling Surface Characteristics." Macromolecular Research 27, no. 12 (August 16, 2019): 1200–1209. http://dx.doi.org/10.1007/s13233-019-7163-8.

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24

Kass, Steven R. "Zwitterion−Dianion Complexes and Anion−Anion Clusters with Negative Dissociation Energies." Journal of the American Chemical Society 127, no. 38 (September 2005): 13098–99. http://dx.doi.org/10.1021/ja053391w.

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25

Li, Dalong, Changlu Gao, Xinyue Wang, Gang Wu, Jinghua Yin, Yudong Huang, and Xiuhua Sun. "Zwitterionic Polysulfone Copolymer/Polysulfone Blended Ultrafiltration Membranes with Excellent Thermostability and Antifouling Properties." Membranes 11, no. 12 (November 26, 2021): 932. http://dx.doi.org/10.3390/membranes11120932.

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Membrane fouling has been one of the most important challenges in membrane separation operations. In this study, we report a facile strategy to prepare antifouling polysulfone (PSf) UF membranes by blending amphiphilic zwitterion polysulfone-co-sulfobetaine polysulfone (PSf-co-SBPSf) copolymer. The copolymer chemical structure was characterized by 1HNMR spectroscopy. The PSf/PSf-co-SBPSf blend membranes with various zwitterionic SBPSf segment contents exhibited better surface hydrophilicity and excellent antifouling ability compared to PSf and PSf/PEG membranes. The significant increase of both porosity and water permeance indicates that the PSf-co-SBPSf has a pore-forming effect. The pure water flux and flux recovery ratio of the PSf/PSf-co-SBPSf blend membranes were both remarked to improve 286.43 L/m2h and 92.26%, while bovine serum albumin (BSA) rejection remained at a high level (97.66%). More importantly, the water flux and BSA rejection see minimal variance after heat treatment, indicating excellent thermostability. Overall, the PSf/PSf-co-SBPSf blend membranes achieved a comprehensive performance of sustainable hydrophilic, high permeation flux, and remarkable antifouling ability, thus becoming a promising candidate in high-temperature separation application.

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26

Sharifi, Faezeh, Mansour Jahangiri, Imran Nazir, Mulazim Hussain Asim, Pedram Ebrahimnejad, Andrea Hupfauf, Ronald Gust, and Andreas Bernkop-Schnürch. "Zeta potential changing nanoemulsions based on a simple zwitterion." Journal of Colloid and Interface Science 585 (March 2021): 126–37. http://dx.doi.org/10.1016/j.jcis.2020.11.054.

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27

Jensen, Jan H., and Mark S. Gordon. "On the Number of Water Molecules Necessary To Stabilize the Glycine Zwitterion." Journal of the American Chemical Society 117, no. 31 (August 1995): 8159–70. http://dx.doi.org/10.1021/ja00136a013.

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28

Smith, Paul E., Liem X. Dang, and B. Montgomery Pettitt. "Simulation of the structure and dynamics of the bis(penicillamine) enkephalin zwitterion." Journal of the American Chemical Society 113, no. 1 (January 1991): 67–73. http://dx.doi.org/10.1021/ja00001a013.

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29

Wang, Meng, Tingting Huang, Meng Shan, Mei Sun, Shasha Liu, and Hai Tang. "Zwitterionic Tröger’s Base Microfiltration Membrane Prepared via Vapor-Induced Phase Separation with Improved Demulsification and Antifouling Performance." Molecules 29, no. 5 (February 25, 2024): 1001. http://dx.doi.org/10.3390/molecules29051001.

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The fouling of separation membranes has consistently been a primary factor contributing to the decline in membrane performance. Enhancing the surface hydrophilicity of the membrane proves to be an effective strategy in mitigating membrane fouling in water treatment processes. Zwitterionic polymers (containing an equimolar number of homogeneously distributed anionic and cationic groups on the polymer chains) have been used extensively as one of the best antifouling materials for surface modification. The conventional application of zwitterionic compounds as surface modifiers is intricate and inefficient, adding complexity and length to the membrane preparation process, particularly on an industrial scale. To overcome these limitations, zwitterionic polymer, directly used as a main material, is an effective method. In this work, a novel zwitterionic polymer (TB)—zwitterionic Tröger’s base (ZTB)—was synthesized by quaternizing Tröger’s base (TB) with 1,3-propane sultone. The obtained ZTB is blended with TB to fabricate microfiltration (MF) membranes via the vapor-induced phase separation (VIPS) process, offering a strategic solution for separating emulsified oily wastewater. Atomic force microscopy (AFM), scanning electron microscopy (SEM), water contact angle, and zeta potential measurements were employed to characterize the surface of ZTB/TB blended membranes, assessing surface morphology, charge, and hydrophilic/hydrophobic properties. The impact of varying ZTB levels on membrane surface morphology, hydrophilicity, water flux, and rejection were investigated. The results showed that an increase in ZTB content improved hydrophilicity and surface roughness, consequently enhancing water permeability. Due to the attraction of water vapor, the enrichment of zwitterionic segments was enriched, and a stable hydration layer was formed on the membrane surface. The hydration layer formed by zwitterions endowed the membrane with good antifouling properties. The proposed mechanism elucidates the membrane’s proficiency in demulsification and the reduction in irreversible fouling through the synergistic regulation of surface charge and hydrophilicity, facilitated by electrostatic repulsion and the formation of a hydration layer. The ZTB/TB blended membranes demonstrated superior efficiency in oil–water separation, achieving a maximum flux of 1897.63 LMH bar−1 and an oil rejection rate as high as 99% in the oil–water emulsion separation process. This study reveals the migration behavior of the zwitterionic polymer in the membrane during the VIPS process. It enhances our comprehension of the antifouling mechanism of zwitterionic membranes and provides guidance for designing novel materials for antifouling membranes.

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30

Lee, Jun Hyuk, Jeong Seok Yeon, Jihoon Kim, Jeong Hee Park, Seong Soo Yoo, Sunghwan Hong, Minjun Kim, Moon Jeong Park, Ho Seok Park, and Pil J. Yoo. "Accelerated Li-ion transport through a zwitterion-anchored separator for high-performance Li–S batteries." Journal of Materials Chemistry A 9, no. 45 (2021): 25463–73. http://dx.doi.org/10.1039/d1ta08422d.

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Zwitterionic sulfobetaine moieties were anchored on a separator surface to concurrently facilitate selective Li-ion transport and polysulfide conversion, finally resulting in significantly enhanced performance for durable Li–S battery operation.

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31

Nazari, Simin, and Amira Abdelrasoul. "Influence of Dipole Orientation of Zwitterionic Materials on Hemodialysis Membrane Interactions with Human Serum Proteins." Applied Sciences 13, no. 23 (November 28, 2023): 12777. http://dx.doi.org/10.3390/app132312777.

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Hemodialysis is a lifesaving treatment for end-stage renal disease (ESRD) that exploits semipermeable membranes to remove fluids and uremic toxins from ESRD patients. Polyethersulfone (PES) is the most common membrane that is currently used in Canadian hospitals and represents 93% of the market. Nevertheless, PES membranes have limited hemocompatibility, which triggers blood activation cascades, as the rate of morbidity and mortality in ESRD patients is still unacceptably high. Surface modification with zwitterionic (ZW) materials, which are well known for their strong dipole–dipole interactions and exceptional antifouling properties, has recently received increased attention in improving PES characteristics like roughness, wettability, and biocompatibility, which are crucial factors in dialysis efficiency. The hydration structures, dynamics, and interactions of ZWs are significantly dependent on the backbone structures, such as differences in carbon space length [CSL], conformation, functional groups, pendant groups, and charge distributions, and even minor changes in ZW structure can drastically alter their behavior. However, a systematic investigation of the impact of dipole orientation of ZW on the hemocompatibility of the membranes has not yet been investigated. This study offers a comprehensive exploration of the interactions between hemodialysis membranes and human serum proteins, emphasizing the pivotal role of the zwitterion dipole orientation. We utilize molecular docking techniques to predict protein–ligand interactions, offering insights into the binding sites and binding energy of these complexes. The effect of dipole orientation on the hemocompatibility of various ZW-modified PES membranes compared to the pristine PES has been investigated using 2-methacryloyloxyethyl phosphorylcholine (MPC), 2-((2-(methacryloyloxy)ethyl)dimethylammonio)ethyl methyl phosphate (MMP), and butyl (2-((2-(methacryloyloxy)ethyl)dimethylammonio)ethyl) phosphate (MBP) zwitterions with opposite dipole orientations. Results showed that the protein–ligand interactions and affinity energies displayed by the reverse dipole moment structures are remarkably different. It was demonstrated that the MBP–PES ligand had the lowest affinity energy to interact with all examined human serum proteins compared to the structure, which had an opposite dipole moment. As a result, this membrane surface has better antifouling properties and, thus, higher hemocompatibility, which directly correlates with greater efficiency of hemodialysis in patients.

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32

Escudero, Carlos, Zoubir El-Hachemi, Joaquim Crusats, and Josep M. Ribó. "Zwitterionic vs porphyrin free-base structures in 4-phenylsulfonic acid meso-substituted porphyrins." Journal of Porphyrins and Phthalocyanines 09, no. 12 (December 2005): 852–63. http://dx.doi.org/10.1142/s1088424605000988.

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The 5,10,15,20-tetrakis(4-sulfophenyl)porphyrin (TPPS4) and 5-phenyl-10,15,20-tris(4-sulfophenyl)porphyrin (TPPS3)] were obtained for the first time as the pure sulfonic acid derivatives and characterized for their constitutional structure in the solid state and in water solution. The zwitterionic species in water solutions, above a critical micellar concentration, are stabilized by side-to-side homoassociation to J-aggregates (B-band: 490 nm), but in solids they only give the J-aggregates when water is present in enough amount. Severe dried solids show a zwitterionic species, stabilized by side-to-side interactions, that probably corresponds to the dimer (B-band: 455 nm). The monomeric zwitterion (B-band: 434 nm) is detected in dilute water solutions and its acid/base properties (concentration pK a (1/2) ≈ 5.0) are not significantly different from those of the acidified solutions of their sodium sulfonate derivatives. However, pure water solutions of TPPS n , in contrast to those of their sodium salts, show important interactions with hydrophilic surfaces: e.g. TPPS4 adsorbs on fused quartz forming a monolayer of the free-base porphyrin together with its counter cations. Dilution of the title porphyrins in a solid matrix (e.g. KBr ) leads to a free-base porphyrin species with a red-shifted B-band (424 nm) that points to a side-to-side homoassociation, which is in contrast with the typical π-stacked aggregates of the corresponding alkaline metal sulfonato salts.

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33

Torres, Lucas C., Roman Dobrovetsky, and Christopher B. Caputo. "Allenic phosphonium borate zwitterions via a phosphonium allenylidene intermediate." Chemical Communications 57, no. 67 (2021): 8272–75. http://dx.doi.org/10.1039/d1cc03249f.

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Wang, Deng, Lei Huang, Qiyin Chen, Luyao Hu, Feng Zeng, Xianyong Zhou, Luozheng Zhang, et al. "A dual function-enabled novel zwitterion to stabilize a Pb–I framework and passivate defects for highly efficient inverted planar perovskite solar cells." Chemical Communications 56, no. 51 (2020): 6929–32. http://dx.doi.org/10.1039/d0cc02613a.

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Dowben, Peter A., Donna A. Kunkel, Axel Enders, Luis G. Rosa, Lucie Routaboul, Bernard Doudin, and Pierre Braunstein. "The Dipole Mediated Surface Chemistry of p-Benzoquinonemonoimine Zwitterions." Topics in Catalysis 56, no. 12 (June 18, 2013): 1096–103. http://dx.doi.org/10.1007/s11244-013-0075-5.

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Li, Xiaofang, Louzhen Fan, Dongfang Liu, Herman H. Y. Sung, Ian D. Williams, Shihe Yang, Kai Tan, and Xin Lu. "Synthesis of a Dy@C82Derivative Bearing a Single Phosphorus Substituent via a Zwitterion Approach." Journal of the American Chemical Society 129, no. 35 (September 2007): 10636–37. http://dx.doi.org/10.1021/ja074321n.

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Ningrum, Eva Oktavia, Eva Lestiana Pratiwi, Isyarah Labbaika Shaffitri, Suprapto Suprapto, Mentari Rachmatika Mukti, Ely Agustiani, Niniek Fajar Puspita, and Achmad Dwitama Karisma. "Developments on Synthesis and Applications of Sulfobetaine Derivatives: A Brief Review." Indonesian Journal of Chemistry 21, no. 5 (August 24, 2021): 1298. http://dx.doi.org/10.22146/ijc.61128.

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Zwitterionic polymers are material families characterized by high dipole moment and highly charged groups. Zwitterionic materials simultaneously possess an equimolar number of cationic and anionic moieties, maintaining overall electroneutrality and high hydrophilicity. Zwitterionic is categorized into three groups: phosphobetaine, carboxybetaine, and sulfobetaine that could form dense and stable hydration shells through the strong ion-dipole interaction among water molecules and zwitterions. As a result of their remarkable hydration capability, low interfacial energy, and marvelous antifouling capacities, these materials have been applied as adsorbing agents, biomedical applications, electronics, hydrogels, and antifouling for membrane separation and marine coatings. This review is focused on polysulfobetaine, which contains sulfonate as a negatively charged group, and quaternary ammonium as a positively charged group. Polysulfobetaine is the most promising one to be applied in the industry since it is commercially available and its monomers are easily prepared. The comparisons of several polysulfobetaine derivatives as antimicrobial, antifouling, surfactant and detergents, biomedical and electronic application, surface modification, and smart hydrogel are presented in this review.

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Yoshizawa-Fujita, Masahiro, Nolene Byrne, Maria Forsyth, Douglas R. MacFarlane, and Hiroyuki Ohno. "Proton Transport Properties in Zwitterion Blends with Brønsted Acids." Journal of Physical Chemistry B 114, no. 49 (December 16, 2010): 16373–80. http://dx.doi.org/10.1021/jp1078949.

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Loiola, Lívia M. D., Marina Batista, Larissa B. Capeletti, Gabriela B. Mondo, Rhubia S. M. Rosa, Rafael E. Marques, Marcio C. Bajgelman, and Mateus B. Cardoso. "Shielding and stealth effects of zwitterion moieties in double-functionalized silica nanoparticles." Journal of Colloid and Interface Science 553 (October 2019): 540–48. http://dx.doi.org/10.1016/j.jcis.2019.06.044.

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Zhang, Huaxin, Qinghua Xia, and Dan Zhou. "Albumin-gated zwitterion-stabilized mesoporous silica nanorod as a pH-responsive drug delivery system." Colloids and Surfaces B: Biointerfaces 193 (September 2020): 111107. http://dx.doi.org/10.1016/j.colsurfb.2020.111107.

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Yue, Wen-Wen, Hui-Juan Li, Tao Xiang, Hui Qin, Shu-Dong Sun, and Chang-Sheng Zhao. "Grafting of zwitterion from polysulfone membrane via surface-initiated ATRP with enhanced antifouling property and biocompatibility." Journal of Membrane Science 446 (November 2013): 79–91. http://dx.doi.org/10.1016/j.memsci.2013.06.029.

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Weinman, Steven T., Maria Bass, Soumya Pandit, Moshe Herzberg, Viatcheslav Freger, and Scott M. Husson. "A switchable zwitterionic membrane surface chemistry for biofouling control." Journal of Membrane Science 548 (February 2018): 490–501. http://dx.doi.org/10.1016/j.memsci.2017.11.055.

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Zhang, Wei, and Timothy M. Swager. "Functionalization of Single-Walled Carbon Nanotubes and Fullerenes via a Dimethyl Acetylenedicarboxylate−4-Dimethylaminopyridine Zwitterion Approach." Journal of the American Chemical Society 129, no. 25 (June 2007): 7714–15. http://dx.doi.org/10.1021/ja0717212.

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Stradiotto, Mark, Judy Cipot, and Robert McDonald. "A Catalytically Active, Charge-Neutral Rh(I) Zwitterion Featuring a P,N-Substituted “Naked” Indenide Ligand." Journal of the American Chemical Society 125, no. 19 (May 2003): 5618–19. http://dx.doi.org/10.1021/ja034543v.

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Malik, Abida Naseem, Akbar Ali, Muhammad Ashfaq, Muhammad Nawaz Tahir, Mohammad Mahtab Alam, Mohamed S. Mostafa, and Aleksey Kuznetsov. "A synthetic approach towards drug modification: 2-hydroxy-1-naphthaldehyde based imine-zwitterion preparation, single-crystal study, Hirshfeld surface analysis, and computational investigation." RSC Advances 14, no. 10 (2024): 6476–93. http://dx.doi.org/10.1039/d3ra08727a.

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This work is about the modification of pyrimethamine and 4-amino-N-(2,3-dihydrothiazol-2-yl)benzenesulfonamide via condensation reaction with 2-hydroxy-1-naphthaldehyde to produce new organic zwitterionic compounds DSPIN and ACPIN in methanol.

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Sanchez-Cano, Carlos, and Mónica Carril. "Recent Developments in the Design of Non-Biofouling Coatings for Nanoparticles and Surfaces." International Journal of Molecular Sciences 21, no. 3 (February 3, 2020): 1007. http://dx.doi.org/10.3390/ijms21031007.

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Biofouling is a major issue in the field of nanomedicine and consists of the spontaneous and unwanted adsorption of biomolecules on engineered surfaces. In a biological context and referring to nanoparticles (NPs) acting as nanomedicines, the adsorption of biomolecules found in blood (mostly proteins) is known as protein corona. On the one hand, the protein corona, as it covers the NPs’ surface, can be considered the biological identity of engineered NPs, because the corona is what cells will “see” instead of the underlying NPs. As such, the protein corona will influence the fate, integrity, and performance of NPs in vivo. On the other hand, the physicochemical properties of the engineered NPs, such as their size, shape, charge, or hydrophobicity, will influence the identity of the proteins attracted to their surface. In this context, the design of coatings for NPs and surfaces that avoid biofouling is an active field of research. The gold standard in the field is the use of polyethylene glycol (PEG) molecules, although zwitterions have also proved to be efficient in preventing protein adhesion and fluorinated molecules are emerging as coatings with interesting properties. Hence, in this review, we will focus on recent examples of anti-biofouling coatings in three main areas, that is, PEGylated, zwitterionic, and fluorinated coatings.

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Wang, Jin, Gotard Burdzinski, Jacek Kubicki, Matthew S. Platz, Robert A. Moss, Xiaolin Fu, Piotr Piotrowiak, and Mykhaylo Myahkostupov. "Ultrafast Spectroscopic Study of the Photochemistry and Photophysics of Arylhalodiazirines: Direct Observation of Carbene and Zwitterion Formation." Journal of the American Chemical Society 128, no. 51 (December 2006): 16446–47. http://dx.doi.org/10.1021/ja067205d.

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Wang, Wentao, Xin Ji, Anshika Kapur, Chengqi Zhang, and Hedi Mattoussi. "A Multifunctional Polymer Combining the Imidazole and Zwitterion Motifs as a Biocompatible Compact Coating for Quantum Dots." Journal of the American Chemical Society 137, no. 44 (October 30, 2015): 14158–72. http://dx.doi.org/10.1021/jacs.5b08915.

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Bush, Matthew F., Jos Oomens, Richard J. Saykally, and Evan R. Williams. "Effects of Alkaline Earth Metal Ion Complexation on Amino Acid Zwitterion Stability: Results from Infrared Action Spectroscopy." Journal of the American Chemical Society 130, no. 20 (May 2008): 6463–71. http://dx.doi.org/10.1021/ja711343q.

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Smith, Paul E., and B. Montgomery Pettitt. "Effects of salt on the structure and dynamics of the bis(penicillamine) enkephalin zwitterion: a simulation study." Journal of the American Chemical Society 113, no. 16 (July 1991): 6029–37. http://dx.doi.org/10.1021/ja00016a015.

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