Synthesis and application of a metal ion coordinating ionic liquid monomer: Towards size and dispersity control of nanoparticles formed within a structured polyelectrolyte

Dreier, Timothy A.; Ringstrand, Bryan S.; Seifert, Sönke; Firestone, Millicent A.

doi:10.1016/j.eurpolymj.2018.08.017

Title: Synthesis and application of a metal ion coordinating ionic liquid monomer: Towards size and dispersity control of nanoparticles formed within a structured polyelectrolyte

Journal Article · Tue Aug 07 00:00:00 EDT 2018 · European Polymer Journal

DOI:https://doi.org/10.1016/j.eurpolymj.2018.08.017· OSTI ID:1473822

^[1]; Ringstrand, Bryan S. ^[1]; Seifert, Sönke ^[2];

^[1]

Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Argonne National Lab. (ANL), Argonne, IL (United States). X-ray Sciences Division

The design, synthesis, and characterization of an amphiphilic ionic liquid (IL) monomer possessing a transition metal coordinating acrylamide moiety is described. Incorporation of the acrylamide moiety is achieved by converting l-histidine into an imidazolium, followed by alkylation to introduce a decyl chain, and acrylation of the α-amino group. The acrylamide containing IL monomer and a co-monomer, poly(ethylene glycol) diacrylate (PEGDA Mn 575), self-assembles into a weakly ordered 2D hexagonal lyotropic mesophase in water (34 ± 2 (w/w)%). Upon photo-irradiation of the mesophase a nanostructured polyelectrolyte retaining the 2D hexagonal structure is produced. Doping the mesophase with Au³⁺ ions prior to photo-irradiation produces plasmonic Au NP copolymer composites only at a threshold mole ratio of IL monomer to gold ions (i.e., onset at 1740:1 mole ratio). At higher monomer to Au³⁺ mole ratios plasmonic NPs are not formed. Evaluation of the in-situ synthesized plasmonic Au NPs by SAXS and optical spectroscopy indicate they are smaller, more uniform spherical particles that resist aggregation upon swelling and de-swelling in ethanol when compared to previously reported composites employing an IL monomer that lacks a metal ion coordination site (e.g., 3-decyl-1-vinylimidazolium IL).

View Accepted Manuscript (DOE)

View Accepted Manuscript (Publisher)

Cite

Export

Save

Research Organization:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States); Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Laboratory Directed Research and Development (LDRD) Program; USDOE National Nuclear Security Administration (NNSA); USDOE Office of Science (SC), Basic Energy Sciences (BES); Los Alamos National Laboratory (LANL); Argonne National Laboratory - Advanced Photon Source

Grant/Contract Number:: AC52-06NA25396; AC02-06CH11357

OSTI ID:: 1473822

Alternate ID(s):: OSTI ID: 1508371; OSTI ID: 1703153

Report Number(s):: LA-UR-18-27591

Journal Information:: European Polymer Journal, Vol. 107, Issue C; ISSN 0014-3057

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 5 works

Citation information provided by
Web of Science

References (54)

Greater than the sum: Synergy and emergent properties in nanoparticle–polymer composites Firestone, Millicent A.; Hayden, Steven C.; Huber, Dale L. MRS Bulletin, Vol. 40, Issue 9 https://doi.org/10.1557/mrs.2015.202	journal	September 2015
Polyelectrolyte Multilayer Nanoreactors for Preparing Silver Nanoparticle Composites: Controlling Metal Concentration and Nanoparticle Size Wang, Tom C.; Rubner, Michael F.; Cohen, Robert E. Langmuir, Vol. 18, Issue 8 https://doi.org/10.1021/la015725a	journal	April 2002
Gold Nanoparticles: Assembly, Supramolecular Chemistry, Quantum-Size-Related Properties, and Applications toward Biology, Catalysis, and Nanotechnology Daniel, Marie-Christine; Astruc, Didier Chemical Reviews, Vol. 104, Issue 1 https://doi.org/10.1021/cr030698+	journal	December 2003
DNA‐Based Assembly of Metal Nanoparticles Niemeyer, Christof M.; Simon, Ulrich European Journal of Inorganic Chemistry, Vol. 2005, Issue 18 https://doi.org/10.1002/ejic.200500425	journal	September 2005
Composite Layer-by-Layer (LBL) Assembly with Inorganic Nanoparticles and Nanowires Srivastava, Sudhanshu; Kotov, Nicholas A. Accounts of Chemical Research, Vol. 41, Issue 12, p. 1831-1841 https://doi.org/10.1021/ar8001377	journal	December 2008
Metal nanoparticle–DNA hybrids – from assembly towards functional conjugates Fischler, Monika; Simon, Ulrich Journal of Materials Chemistry, Vol. 19, Issue 11 https://doi.org/10.1039/b812225c	journal	January 2009
Versatile electrostatic assembly of nanoparticles and polyelectrolytes: Coating, clustering and layer-by-layer processes Chapel, J. -P.; Berret, J. -F. Current Opinion in Colloid & Interface Science, Vol. 17, Issue 2 https://doi.org/10.1016/j.cocis.2011.08.009	journal	April 2012
Glyconanoparticles as multifunctional and multimodal carbohydrate systems Marradi, Marco; Chiodo, Fabrizio; García, Isabel Chemical Society Reviews, Vol. 42, Issue 11 https://doi.org/10.1039/c2cs35420a	journal	January 2013
Peptide mediated formation of noble metal nanoparticles — controlling size and spatial arrangement Corra, Stefano; Shoshan, Michal S.; Wennemers, Helma Current Opinion in Chemical Biology, Vol. 40 https://doi.org/10.1016/j.cbpa.2017.09.005	journal	October 2017
Design of ZIF-8/ion copolymer hierarchically porous material: Coordination effect on the adsorption and diffusion for carbon dioxide Guo, Qirui; Chen, Chong; Zhou, Lijin Microporous and Mesoporous Materials, Vol. 261 https://doi.org/10.1016/j.micromeso.2017.11.007	journal	May 2018
Colloidal metal nanoparticles dispersed in amphiphilic polymers Mayer, Andrea B. R. Polymers for Advanced Technologies, Vol. 12, Issue 1-2 https://doi.org/10.1002/1099-1581(200101/02)12:1/2<96::AID-PAT943>3.0.CO;2-G	journal	January 2001
Synthesis of Two Types of Nanoparticles in Polyelectrolyte Capsule Nanoreactors and Their Dual Functionality Choi, Won San; Koo, Hye Young; Park, Jeong-Ho Journal of the American Chemical Society, Vol. 127, Issue 46 https://doi.org/10.1021/ja053981u	journal	November 2005
Amine-Rich Polyelectrolyte Multilayer Nanoreactors for in Situ Gold Nanoparticle Synthesis Chia, Khek-Khiang; Cohen, Robert E.; Rubner, Michael F. Chemistry of Materials, Vol. 20, Issue 21 https://doi.org/10.1021/cm802166s	journal	October 2008
A Facile and Controllable Strategy to Synthesize Au−Ag Alloy Nanoparticles within Polyelectrolyte Multilayer Nanoreactors upon Thermal Reduction Shang, Li; Jin, Lihua; Guo, Shaojun Langmuir, Vol. 26, Issue 9 https://doi.org/10.1021/la9040612	journal	December 2009
Preparing water-dispersed palladium nanoparticles via polyelectrolyte nanoreactors Coulter, Matthew M.; Dinglasan, Jose Amado; Goh, Jane B. Chemical Science, Vol. 1, Issue 6 https://doi.org/10.1039/c0sc00314j	journal	January 2010
Layer-by-Layer Assembled Mixed Spherical and Planar Gold Nanoparticles: Control of Interparticle Interactions Malikova, Natalie; Pastoriza-Santos, Isabel; Schierhorn, Martin Langmuir, Vol. 18, Issue 9 https://doi.org/10.1021/la025563y	journal	April 2002
Ionogel-Templated Synthesis and Organization of Anisotropic Gold Nanoparticles Firestone, Millicent A.; Dietz, Mark L.; Seifert, Sönke Small, Vol. 1, Issue 7 https://doi.org/10.1002/smll.200500030	journal	July 2005
Solvent-Mediated Plasmon Tuning in a Gold-Nanoparticle-Poly(Ionic Liquid) Composite Batra, D.; Seifert, S.; Varela, L. M. Advanced Functional Materials, Vol. 17, Issue 8 https://doi.org/10.1002/adfm.200600797	journal	April 2007
Conductivity of ionic liquid-derived polymers with internal gold nanoparticle conduits Lee, Sungwon; Cummins, Matthew D.; Willing, Gerold A. Journal of Materials Chemistry, Vol. 19, Issue 43 https://doi.org/10.1039/b910059h	journal	January 2009
Electrochemical Activity of Glucose Oxidase on a Poly(ionic liquid)–Au Nanoparticle Composite Lee, Sungwon; Ringstrand, Bryan S.; Stone, David A. ACS Applied Materials & Interfaces, Vol. 4, Issue 5 https://doi.org/10.1021/am300629n	journal	May 2012
Self-Assembly Directed Organization of Nanodiamond During Ionic Liquid Crystalline Polymer Formation Ringstrand, Bryan S.; Seifert, Sönke; Podlesak, David W. Macromolecular Rapid Communications, Vol. 37, Issue 14 https://doi.org/10.1002/marc.201600070	journal	May 2016
Design principles from multiscale simulations to predict nanostructure in self-assembling ionic liquids Nebgen, Benjamin T.; Magurudeniya, Harsha D.; Kwock, Kevin W. C. Faraday Discussions, Vol. 206 https://doi.org/10.1039/C7FD00154A	journal	January 2018
Functionalized Ionic Liquids for the Synthesis of Metal Nanoparticles and their Application in Catalysis Luska, Kylie L.; Moores, Audrey ChemCatChem, Vol. 4, Issue 10, p. 1534-1546 https://doi.org/10.1002/cctc.201100366	journal	December 2011
Metal-containing ionic liquids: current paradigm and applications Zazybin, A. G.; Rafikova, Kh; Yu, V. Russian Chemical Reviews, Vol. 86, Issue 12 https://doi.org/10.1070/RCR4743	journal	December 2017
On the structural and surface properties of transition-metal nanoparticles in ionic liquids Dupont, Jairton; Scholten, Jackson D. Chemical Society Reviews, Vol. 39, Issue 5 https://doi.org/10.1039/b822551f	journal	January 2010
Organized 3D-alkyl imidazolium ionic liquids could be used to control the size of in situ generated ruthenium nanoparticles? Gutel, Thibaut; Santini, Catherine C.; Philippot, Karine Journal of Materials Chemistry, Vol. 19, Issue 22 https://doi.org/10.1039/b821659b	journal	January 2009
Size-Selective Synthesis of Gold and Platinum Nanoparticles Using Novel Thiol-Functionalized Ionic Liquids Kim, Ki-Sub; Demberelnyamba, D.; Lee, Huen Langmuir, Vol. 20, Issue 3 https://doi.org/10.1021/la0355848	journal	February 2004
On the formation of anisotropic gold nanoparticles by sputtering onto a nitrile functionalised ionic liquid Wender, Heberton; Migowski, Pedro; Feil, Adriano F. Physical Chemistry Chemical Physics, Vol. 13, Issue 30 https://doi.org/10.1039/c1cp21406c	journal	January 2011
Ionic Liquid Anion Controlled Nanoscale Gold Morphology Grown at a Liquid Interface Bhawawet, Nakara; Essner, Jeremy B.; Wagle, Durgesh V. Langmuir, Vol. 33, Issue 24 https://doi.org/10.1021/acs.langmuir.7b00296	journal	June 2017
Optically active histidin-2-ylidene stabilised gold nanoparticles Young, Adam J.; Serpell, Christopher J.; Chin, Jia Min Chemical Communications, Vol. 53, Issue 92 https://doi.org/10.1039/C7CC07602A	journal	January 2017
Coordination chemistry of acrylamide Girma, K. B.; Lorenz, Volker; Blaurock, Steffen Coordination Chemistry Reviews, Vol. 249, Issue 11-12 https://doi.org/10.1016/j.ccr.2005.01.028	journal	June 2005
A Practical in situ Generation of the Schwartz Reagent. Reduction of Tertiary Amides to Aldehydes and Hydrozirconation Zhao, Yigang; Snieckus, Victor Organic Letters, Vol. 16, Issue 2 https://doi.org/10.1021/ol403183a	journal	December 2013
A New Imidazole-Containing Imidazolidinone Catalyst for Organocatalyzed Asymmetric Conjugate Addition of Nitroalkanes to Aldehydes Hojabri, Leila; Hartikka, Antti; Moghaddam, Firouz Matloubi Advanced Synthesis & Catalysis, Vol. 349, Issue 4-5 https://doi.org/10.1002/adsc.200600316	journal	March 2007
Design and Scalable Synthesis of New Chiral Selectors. Part 2: Chiral Ionic Liquids Derived from Diaminocyclohexane and Histidine Zgonnik, Viacheslav; Gonella, Silvia; Mazières, Marie-Rose Organic Process Research & Development, Vol. 16, Issue 2 https://doi.org/10.1021/op200082a	journal	July 2011
(S)-Histidine: the ideal precursor for a novel family of chiral aminoacid and peptidic ionic liquids Guillen, Frédéric; Brégeon, Delphine; Plaquevent, Jean-Christophe Tetrahedron Letters, Vol. 47, Issue 8 https://doi.org/10.1016/j.tetlet.2005.12.090	journal	February 2006
Formation of a Liquid-Crystalline Interpenetrating Poly(ionic liquid) Network Hydrogel Becht, Gregory A.; Sofos, Marina; Seifert, Sönke Macromolecules, Vol. 44, Issue 6 https://doi.org/10.1021/ma102146r	journal	March 2011
Cytoskeleton Mimetic Reinforcement of a Self-Assembled N,N ′-Dialkylimidazolium Ionic Liquid Monomer by Copolymerization Grubjesic, Simonida; Seifert, Sönke; Firestone, Millicent A. Macromolecules, Vol. 42, Issue 15 https://doi.org/10.1021/ma900905k	journal	August 2009
Cations Bind Only Weakly to Amides in Aqueous Solutions Okur, Halil I.; Kherb, Jaibir; Cremer, Paul S. Journal of the American Chemical Society, Vol. 135, Issue 13 https://doi.org/10.1021/ja3119256	journal	March 2013
Au(III) interaction with Methionine- and Histidine-containing peptides Ivanova, Bojidarka B.; Mitewa, Mariana Io. Journal of Coordination Chemistry, Vol. 57, Issue 3 https://doi.org/10.1080/00958970410001671192	journal	February 2004
MnO2-Vertical graphene nanosheets composite electrodes for energy storage devices Ghosh, Subrata; Gupta, Bhavana; Ganesan, K. Materials Today: Proceedings, Vol. 3, Issue 6 https://doi.org/10.1016/j.matpr.2016.04.060	journal	January 2016
Spectroscopy of Hydrothermal Reactions 25: Kinetics of the Decarboxylation of Protein Amino Acids and the Effect of Side Chains on Hydrothermal Stability Li, Jun; Brill, Thomas B. The Journal of Physical Chemistry A, Vol. 107, Issue 31 https://doi.org/10.1021/jp0224766	journal	July 2003
Growth and characterization of a new potential second harmonic generation material from the amino acid family: L-Valinium picrate Martin Britto Dhas, S. A.; Natarajan, S. Crystal Research and Technology, Vol. 43, Issue 8 https://doi.org/10.1002/crat.200711152	journal	August 2008
Thermal decomposition of acrylamide from polyacrylamide: Time-resolved pyrolysis with ion-attachment mass spectrometry Kitahara, Yuki; Okuyama, Ko; Ozawa, Keita Journal of Thermal Analysis and Calorimetry, Vol. 110, Issue 1 https://doi.org/10.1007/s10973-012-2544-7	journal	July 2012
Vibrational analysis of molten poly(ethylene glycol) Matsuura, Hiroatsu; Miyazawa, Tatsuo Journal of Polymer Science Part A-2: Polymer Physics, Vol. 7, Issue 10 https://doi.org/10.1002/pol.1969.160071009	journal	October 1969
Swelling behavior and determination of diffusion characteristics of acrylamide-acrylic acid hydrogels I??k, Belma Journal of Applied Polymer Science, Vol. 91, Issue 2 https://doi.org/10.1002/app.13270	journal	January 2003
Cascade synthesis of a gold nanoparticle–network polymer composite Grubjesic, Simonida; Ringstrand, Bryan S.; Jungjohann, Katherine L. Nanoscale, Vol. 8, Issue 5 https://doi.org/10.1039/C5NR06594A	journal	January 2016
Coordination Chemistry of Acrylamide 2. Classical Complexes of Acrylamide with Manganese(II), Iron(II) and Nickel(II) Chlorides: Syntheses and Crystal Structures Girma, K. B.; Lorenz, Volker; Blaurock, Steffen Zeitschrift für anorganische und allgemeine Chemie, Vol. 631, Issue 13-14 https://doi.org/10.1002/zaac.200500132	journal	October 2005
Coordination Chemistry of Acrylamide: 1. Cobalt(II) Chloride Complexes with Acrylamide - Synthesis and Crystal Structures Girma, K. B.; Lorenz, Volker; Blaurock, Steffen Zeitschrift für anorganische und allgemeine Chemie, Vol. 631, Issue 8 https://doi.org/10.1002/zaac.200500027	journal	June 2005
Growth of New Nonlinear Optical Crystals of Hydrochlorides of l -Histidine from Solution Kannan, V.; Ganesh, R. Bairava; Ramasamy, P. Crystal Growth & Design, Vol. 6, Issue 8 https://doi.org/10.1021/cg0601960	journal	August 2006
The Promise of Self-Assembled 3D Supramolecular Coordination Complexes for Biomedical Applications Casini, Angela; Woods, Benjamin; Wenzel, Margot Inorganic Chemistry, Vol. 56, Issue 24 https://doi.org/10.1021/acs.inorgchem.7b02599	journal	November 2017
Extreme condition nanocarbon formation under air and argon atmospheres during detonation of composition B-3 Huber, Rachel C.; Ringstrand, Bryan S.; Dattelbaum, Dana M. Carbon, Vol. 126 https://doi.org/10.1016/j.carbon.2017.10.008	journal	January 2018
Manipulating Local Ligand Environments for the Controlled Nucleation of Metal Nanoparticles and their Assembly into Nanodendrites Ortiz, Nancy; Skrabalak, Sara E. Angewandte Chemie International Edition, Vol. 51, Issue 47 https://doi.org/10.1002/anie.201205956	journal	October 2012
On the Dual Roles of Ligands in the Synthesis of Colloidal Metal Nanostructures Ortiz, Nancy; Skrabalak, Sara E. Langmuir, Vol. 30, Issue 23 https://doi.org/10.1021/la404539p	journal	January 2014
Magic Numbers of Gold Clusters Stabilized by PVP Tsunoyama, Hironori; Tsukuda, Tatsuya Journal of the American Chemical Society, Vol. 131, Issue 51 https://doi.org/10.1021/ja908188f	journal	December 2009

Similar Records

Multiscale additive manufacturing of polymers using 3D photo-printable self-assembling ionic liquid monomers

Journal Article · Mon Apr 08 00:00:00 EDT 2019 · Molecular Systems Design & Engineering · OSTI ID:1473822

Ndefru, Bineh Gese; Ringstrand, Bryan Scott; Diouf, Sokhna Issa-Yacine Faye; +5 more

3D Volumetric Structural Hierarchy Induced by Colloidal Polymerization of a Quantum-Dot Ionic Liquid Monomer Conjugate

Journal Article · Wed Apr 15 00:00:00 EDT 2020 · Macromolecules · OSTI ID:1473822

Welch, Paul M.; Dreier, Timothy A.; Magurudeniya, Harsha D.; +10 more

Reversible hierarchical structure induced by solvation and temperature modulation in an ionic liquid-based random bottlebrush copolymer

Journal Article · Thu Sep 06 00:00:00 EDT 2018 · Polymer Chemistry · OSTI ID:1473822

Magurudeniya, Harsha D.; Ringstrand, Bryan S.; Seifert, Sönke; +1 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
77 NANOSCIENCE AND NANOTECHNOLOGY
Inorganic and Physical Chemistry
Material Science
Poly(ionic liquid)s
Metal coordinating
Nanostructured
Plasmonic nanoparticles
Acrylamide IL
acrylamide IL
nanostructured
plasmonic nanoparticles

Title: Synthesis and application of a metal ion coordinating ionic liquid monomer: Towards size and dispersity control of nanoparticles formed within a structured polyelectrolyte

Citation Formats

References (54)

Similar Records

Related Subjects