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Division of Polymer Chemistry (POLY) Division of Polymer Chemistry (POLY) Graphical Abstracts Submitted for the 250th ACS National Meeting & Exposition INNOVATION FROM DISCOVERY TO APPLICATION August 16-20, 2015 | Boston, MA Division of Polymer Chemistry (POLY) Table of Contents [click on a session time (AM/PM/EVE) for link to abstracts] Session SUN MON TUE WED THU AM AM Protein-Like Structure & Activity in Synthetic Systems EVE PM PM General Topics: New Synthesis & Characterization of AM AM AM AM EVE Polymers PM PM PM PM AM Surface Modification of Polymeric Materials AM EVE PM AM AM AM Silicones PM PM PM EVE Herman Mark Scholars Award Symposium in Honor of AM Stuart Rowan PM AM Ring Opening Polymerization AM EVE PM PM1 Industrial Innovations in Polymer Chemistry PM2 Biomacromolecules/Macromolecules Young Investigator PM Award Herman Mark Award Symposium in Honor of Timothy AM Lodge Value of Basic Research in Solving Industrial Polymer AM Problems PM Henkel Award for Outstanding Graduate Research in AM Polymer Chemistry Henry A. Hill Centennial Symposium: Innovation in AM Polymer Science PM Multi-component & Sequential Reactions in Polymer PM AM Science: Efficient Synthesis of Structural Diverse AM EVE PM Polymers PM AM AM Ionic Liquids in Polymer Design: From Energy to Health EVE PM PM Charles Overberger Award Symposium in Honor of AM Krzysztof Matyjaszewski PM Herman Mark Young Scholars Award Symposium in AM Honor of Bradley Olsen PM Note: ACS does not own copyrights to the individual abstracts. For permission, please contact the author(s) of the abstract. POLY 1: Modular approach to single chain nanoparticles using alternating radical copolymerization Christopher Lyon1, [email protected], Erik B. Berda2. (1) Chemistry, University of New Hampshire, Durham, New Hampshire, United States (2) Department of Chemistry, University of New Hampshire, Durham, New Hampshire, United States Herein we report on a modular synthesis of single-chain polymer nanoparticles (SCNP) based on alternating radical polymerization of pendant stilbene-derived units. Poly(styrene-co-(4-vinylbenzyltriphenylphosphonium tetrafluoroborate)) was synthesized using RAFT polymerization. This polymer was functionalized with stilbene- derived units via the Wittig reaction with various benzaldehyde derivatives. These polymers were then heated in dilute solution in the presence of a radical source and maleic anhydride or various N-substituted maleimides to produce SCNP. Hydrolysis of or nucleophilic addition to maleic anhydride units leads to further opportunities for functionalization. The ability to add various functionality at each step of this process highlights the modularity of this approach. POLY 2: Supramolecular polymerization from synthetic polypeptide-grafted subunits Jing Wang1, Hongwei Xia1, Hua Lu2, Jianjun Cheng2, Yao Lin1, [email protected]. (1) Inst of Materials Sci, University of Connecticut, Storrs Mansfield, Connecticut, United States (2) Materials Science and Engineering, University of Illinois at Urbana- Champaign, Urbana, Illinois, United States The helical and tubular structures self‐assembled from proteins have inspired scientists to design synthetic subunits that can be “polymerized” into supramolecular polymers through coordinated, non-covalent interactions. However, chain-growth polymerization from synthetic macromolecules or nanoparticles remains a challenge because of the difficulty of controlling the interactions of these large subunits. Herein we discuss the synthesis of homopolypeptide-grafted comb polymers and nanoparticles, and the use of the tunable polypeptide interactions in solution to achieve the controlled assembly. The study shows that the chain growth of supramolecular polymers can be achieved from these synthetic subunits and the process occurs in two distinct stages, with a slow nucleation step followed by a faster chain propagation step. We discuss how the electrostatic interactions between the weakly charged monomers may play an important role in the polymerization process. POLY 3: Accessing polyolefins with novel architectures Hong Li1, Christopher Roland1, Giovanni Rojas2, Adam S. Veige1, Kenneth B. Wagener1, [email protected]. (1) Dept. of Chemistry, University of Florida, Gainesville, Florida, United States (2) Facultad de ciencias, Universidad Icesi, Cali, Colombia We report the synthesis of polyolefins with cyclic and long-chain branched linear structures. By using a highly active pincer ligand-supported tungsten catalyst, we obtained cyclic poly(phenylacetylene) in 94% yield from phenylacetylene in 5 minutes. The cyclic topology was confirmed by gel permeation chromatography (GPC), as well as dynamic (DLS) and static (SLS) light scattering. We also used ADMET polymerization to prepare a series of linear low-density polyethylenes containing alkyl th st th pendent groups (-C21H43) precisely placed on every 15 , 21 or 39 carbon to study the influence of long alkyl branches on polyethylene crystal morphology. 1H and 13C NMR confirmed the precise nature of the polymer structures. Differential scanning calorimetry (DSC) of these three long-chain branch-containing polymers showed melting behaviors not observed in previously reported polyethylenes containing short-chain branches (e.g., ethyl groups) at identical frequencies. POLY 4: Synthesis of conjugated polymers and biomimetic approach for the control of the secondary structures Fumio Sanda, [email protected]. Dept Chem Mtrl Eng, Fac Chem Mtrl Bioeng, Kansai University, Suita Osaka, Japan Biomacromolecules such as proteins and DNA exhibit sophisticated and intricate functions largely depending on their well-defined higher order structures. Artificial helical polymers including poly(methacrylate)s, poly(isocyanide)s, poly(silane)s, poly(phenyleneethynylene)s and poly(acetylene)s have been extensively synthesized for the last several decades. Artificial helical conjugated polymers are important not only from the viewpoint of fundamental study but also for their potential use in practical applications such as molecular recognition, chiral catalysis, and chemical sensing based on their electric and optical properties. In this paper, the author reports the synthesis of helically folded various novel D-hydroxyphenylglycine-derived poly(m- phenyleneethynylene-p-phenyleneethynylene)s. The driving forces for helix formation of these polymers are (1) π-stacking between the phenylene moieties on the main chain, (2) intramolecular hydrogen bonding between the amide groups at the side chains, and (3) amphiphilicity caused by the hydrophobic exterior (alkyl groups and phenyleneethynylene main chain) and hydrophilic interior (hydroxy groups). It should be noteworthy that the amphiphilic balance of the helices formed by these polymers is opposite to that of typical poly(m-phenyleneethynylene) derivatives reported so far. Poly(phenyleneethynylene)s bearing azobenzene moieties in the main chains undergo a reversible conformational change between folded and unfolded structures upon UV and visible light irradiation as a result of trans−cis isomerization of the azobenzene moieties. References F. Sanda and coworkers, Macromolecules 2009, 42, 6115; Polymer 2010, 51, 2255; Macromolecules 2011, 44, 3338; Polymer 2012, 53, 2559; Macromolecules 2013, 46, 4378; Macromolecules 2013, 46, 8161; Macromolecules 2014, 47, 1594; Chem. Lett. 2014, 43, 1622. POLY 5: Radical polymerization ketenes Yuanhui Xiang, Riki Drout, Tyler Densmore, Emily Pentzer, [email protected]. Chemistry, Case Western Reserve University, Cleveland, Ohio, United States Organic materials find widespread application in a number of different materials and medicinal systems. Among the techniques to prepare polymers, radical polymerization is especially attractive as it is routinely used on an industrial scale and can be performed without metal catalysts, preventing product contamination that plagues many applications of polymers. We will report the radical polymerization of isopropylsilyl ketene to give polymers with a high degree of backbone functionality that can be used for further derivatization. The influence of initiating radical identity and reaction conditions will be reported in the context of structures formed from polymerization, specifically polyester, polyketene acetal and polyketone. POLY 6: Rational design of macromolecular superstructures Ke Zhang, [email protected]. Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, United States Protein-protein interactions are at the core of the interactomics system of any cells because they are highly directional, specific, and reversible, characteristics that synthetic chemists have yet to fully emulate. Here, we aim to mimic some of the precision assembly ability that natural proteins exhibit by extracting the requirements for such assembly, and recreating them in new forms accessible to modern polymer and organic chemistry. Towards this goal, we have designed conjugates of polymer brush and DNA, wherein the brush serves as a steric steer to guide DNA hybridization in a fixed dimension, while the DNA serves as a functional group equivalent to connect with desired partner brushes. With this approach, a new class of superpolymers with controlled architecture, macromonomer sequence, and end-group functionality is possible. POLY 7: From laboratory to human clinical trials: A successful investigational new drug application for detecting early stage cardiovascular disease Alaina McGrath2, [email protected], Eric D. Pressly2, Yongjian Liu3, Richard Laforest3, Hannah Luehmann3,
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