654
Views
0
CrossRef citations to date
0
Altmetric
Articles

Polystyrene supramolecular networks based on DA-AD hydrogen bonds

, , , , &
Pages 486-499 | Received 17 Jan 2015, Accepted 23 Feb 2015, Published online: 26 May 2015

References

  • Aakeröy C, Epa K. Controlling supramolecular assembly using electronic effects. Top Curr. Chem. 2012;1–23.
  • Du JZ, Tang YP, Lewis AL, Armes SP, pH-sensitive vesicles based on a biocompatible zwitterionic diblock copolymer. J. Am. Chem. Soc. 2005;17982–17983.
  • Lee OS, Stupp SI, Schatz GC. Atomistic molecular dynamics simulations of peptide amphiphile self-assembly into cylindrical nanofibers. J. Am. Chem. Soc. 2011;133:3677–3683.10.1021/ja110966y
  • Ghosh A, Lee WB. Numerical studies on the thermal tuning of domain size in supramolecular diblock copolymer melts. Macromol. Res. 2011;19:483–486.10.1007/s13233-011-0510-z
  • Lehn JM. Supramolecular chemistry – scope and perspectives molecules, supermolecules, and molecular devices (nobel lecture). Angew. Chem. Int. Ed. Engl. 1988;27:89–112.10.1002/(ISSN)1521-3773
  • Binder WH, Zirbs R. Supramolecular polymers and networks with hydrogen bonds in the main- and side-chain. Hydrogen Bond. Polym. 2007;207:1–78.
  • Patra D, Ramesh M, Sahu D, Padhy H, Chu CW, Wei KH, Lin HC. Enhancement of photovoltaic properties in supramolecular polymer networks featuring a solar cell main-chain polymer H-bonded with conjugated cross-linkers. Polymer. 2012;53:1219–1228.10.1016/j.polymer.2012.01.026
  • Wan DC, Chen F, Kakuchi T, Satoh T. Guest release and solution behavior of a hydrogen-bonding physical micelle during chemoresponsive shell disruption. Polymer. 2011;52:3405–3412.10.1016/j.polymer.2011.05.025
  • Chen XM, Lu XM, Cui K, Cui W, Wu J, Lu QH. Precipitation supramolecular complex for photoinduced anisotropic material with dual mesogenic units. Polymer. 2011;52:3243–3250.10.1016/j.polymer.2011.02.023
  • Chiang WH, Lan YJ, Huang YC, Chen YW, Huang YF, Lin SC, Chern CS, Chiu HC. Multi-scaled polymersomes from self-assembly of octadecanol-modified dextrans. Polymer. 2012;53:2233–2244.10.1016/j.polymer.2012.03.030
  • Chen YY, Lin HC. Metallo-homopolymer and metallo-copolymers containing light-emitting poly(fluorene/ethynylene/(terpyridyl)zinc(II)) backbones and 1,3,4-oxadiazole (OXD) pendants. Polymer. 2007;48:5268–5278.10.1016/j.polymer.2007.06.040
  • Zou G, Wang YL, Zhang QJ, Kohn H, Manaka T, Iwamoto M. Molecular structure modulated properties of azobenzene-substituted polydiacetylene LB films: chirality formation and thermal stability. Polymer. 2010;51:2229–2235.10.1016/j.polymer.2010.03.029
  • Folmer BJB, Sijbesma RP, Versteegen RM, van der Rijt JAJ, Meijer EW. Supramolecular polymer materials: chain extension of telechelic polymers using a reactive hydrogen-bonding synthon. Adv. Mater. 2000;12:874–878.10.1002/(ISSN)1521-4095
  • Rieth LR, Eaton RF, Coates GW. Polymerization of ureidopyrimidinone-functionalized olefins by using late-transition metal ziegler-natta catalysts: synthesis of thermoplastic elastomeric polyolefins. Angew. Chem.-Int. Ed. 2001;40:2153–2156.10.1002/(ISSN)1521-3773
  • Bureiko SF, Denisov GS. Dynamics of molecular hydrogen exchange in hydrogen-bonded systems. Pol. J. Chem. 2002;76:1177–1190.
  • Bureiko SF, Denisov GS. Spectroscopic study of hydrogen exchange processes and structure of intermediate complexes with intermolecular hydrogen bonds. J. Mol. Struct. 2004;700:49–53.10.1016/j.molstruc.2003.11.054
  • Adamson AW. A textbook of physical chemistry. New York (NY): Academic Press; 1986.
  • Schalley C. Analytical methods in supramolecular chemistry. Weinheim: Wiley-vch Verlag GmbH & Co. KGaA; 2007.
  • Ilhan F, Gray M, Rotello VM. Reversible side chain modification through noncovalent interactions. “Plug and Play” polymers. Macromolecules. 2001;34:2597–2601.10.1021/ma001700r
  • Chen JS, Rosenberger F. Accurate NMR data evaluation for monomer shift, dimer shift and dimerization constant in a self associating system. Tetrahedron Lett. 1990;31:3975–3978.
  • Horman I, Dreux B. Estimation of dimerisation constants from complexatin-induced displacements of 1H NMR chemical shifts: dimerisation of caffeine. Helv. Chim. Acta. 1984;67:754–764.10.1002/(ISSN)1522-2675
  • Ośmiałowski B, Kolehmainen E, Dobosz R, Gawinecki R, Kauppinen R, Valkonen A, Koivukorpi J, Rissanen K. Self-organization of 2-acylaminopyridines in the solid state and in solution. J. Phys. Chem. A. 2010;114:10421–10426.10.1021/jp1063116
  • Ośmiałowski B, Kolehmainen E, Kalenius E, Behera B, Kauppinen R, Sievänen E. Intermolecular steric hindrance in 7-acylamino-[1H]-2-oxo-1,8-naphthyridines: NMR, ESI-MS, IR, and DFT calculation studies. Struct. Chem. 2011;22:1143–1151.10.1007/s11224-011-9808-x
  • Beijer FH, Sijbesma RP, Kooijman H, Spek AL, Meijer EW. Strong dimerization of ureidopyrimidones via quadruple hydrogen bonding. J. Am. Chem. Soc. 1998;120:6761–6769.10.1021/ja974112a
  • Brunsveld L, Folmer BJB, Meijer EW, Sijbesma RP. Supramolecular polymers. Chem. Rev. 2001;101:4071–4098.10.1021/cr990125q
  • Hirschberg J, Beijer FH, van Aert HA, Magusin P, Sijbesma RP, Meijer EW. Supramolecular polymers from linear telechelic siloxanes with quadruple-hydrogen-bonded units. Macromolecules. 1999;32:2696–2705.10.1021/ma981950w
  • De Greef TFA, Smulders MMJ, Wolffs M, Schenning A, Sijbesma RP, Meijer EW. Supramolecular polymerization. Chem. Rev. 2009;109:5687–5754.10.1021/cr900181u
  • Oishi T, Lee YK, Nakagawa A, Onimura K, Tsutsumi H. Syntheses and polymerizations of novel chiral poly(acrylamide) macromonomers and their chiral recognition abilities. J. Polym. Sci. Part A: Polym. Chem. 2002;40:1726–1741.10.1002/(ISSN)1099-0518
  • Kao HC, Kuo SW, Chang FC. Effects of inert diluent segment and hydrogen bonding in poly(styrene-co-methacrylamide) copolymers. J. Polym. Res. 2003;10:111–117.10.1023/A:1024978102847
  • Coskun M, Tem¨¹z MM, Demirelli K, Characterization and thermal degradation of poly (2-methacrylamidopyridine). Pol. Degrad. Stab. 77 (2002) 371–376.
  • Coşkun M, Barim G, Temüz MM, Demirelli K. A study on thermal stabilities of poly(2-methacrylamidopyridine)-poly(methyl methacrylate) blends. Polym.-Plas. Technol. Eng. 2005;44:677–686.10.1081/PTE-200057816
  • Woodward PJ, Hermida Merino DH, Greenland BW, Hamley IW, Light Z, Slark AT, Hayes W. Hydrogen bonded supramolecular elastomers: correlating hydrogen bonding strength with morphology and rheology. Macromolecules. 2010;43:2512–2517.10.1021/ma9027646
  • Corbin PS, Zimmerman SC. Self-association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen-bonded dimers. J. Am. Chem. Soc. 1998;120:9710–9711.10.1021/ja981884d
  • Lange RFM, Van Gurp M, Meijer EW. Hydrogen-bonded supramolecular polymer networks. J. Polym. Sci. Part A: Polym. Chem. 1999;37:3657–3670.10.1002/(ISSN)1099-0518
  • Hofmeier H, Hoogenboom R, Wouters MEL, Schubert US. High molecular weight supramolecular polymers containing both terpyridine metal complexes and ureidopyrimidinone quadruple hydrogen-bonding units in the main chain. J. Am. Chem. Soc. 2005;127:2913–2921.10.1021/ja042919e
  • Söntjens SHM, Sijbesma RP, van Genderen MHP, Meijer EW. Stability and lifetime of quadruply hydrogen bonded 2-ureido-4[1H]-pyrimidinone dimers. J. Am. Chem. Soc. 2000;122:7487–7493.10.1021/ja000435m
  • Feldman KE, Kade MJ, Meijer E, Hawker CJ, Kramer EJ. Model transient networks from strongly Hydrogen-bonded polymers. Macromolecules. 2009;42:9072–9081.10.1021/ma901668w
  • Subramani C, Dickert S, Yeh YC, Tuominen MT, Rotello VM. Supramolecular functionalization of electron-beam generated nanostructures. Langmuir. 2011;27:1543–1545.10.1021/la1039514
  • McKee MG, Elkins CL, Park T, Long TE. Influence of random branching on multiple hydrogen bonding in poly(alkyl methacrylate)s. Macromolecules. 2005;38:6015–6023.10.1021/ma050667b
  • Park T, Zimmerman SC. Formation of a miscible supramolecular polymer blend through self-assembly mediated by a quadruply hydrogen-bonded heterocomplex. J. Am. Chem. Soc. 2006;128:11582–11590.10.1021/ja0631854
  • Park T, Zimmerman SC. Interplay of fidelity, binding strength, and structure in supramolecular polymers. J. Am. Chem. Soc. 2006;128:14236–14237.10.1021/ja065469u
  • Sartorius J, Schneider HJ. A general scheme based on empirical increments for the prediction of hydrogen-bond associations of nucleobases and of synthetic host–guest complexes. Chem. – A Eur. J. 1996;2:1446–1452.10.1002/(ISSN)1521-3765
  • Hisamatsu Y, Fukumi Y, Shirai N, Ikeda S-I, Odashima K. Five-membered heterocyclic ureas suitable for the donor–donor–acceptor hydrogen-bonding modules. Tetrahedron Lett. 2008;49:2005–2009.10.1016/j.tetlet.2008.01.068
  • Zimmerman SC, Corbin FS. Heteroaromatic modules for self-assembly using multiple hydrogen bonds. Mol. Self-Assembly. 2000;96:63–94.
  • Plante A, Mauran D, Carvalho SP, Pagé J, Pellerin C, Lebel O. Tg and rheological properties of triazine-based molecular glasses: incriminating evidence against hydrogen bonds. J. Phys. Chem. B. 2009;113:14884–14891.10.1021/jp905268a
  • Chapkanov AG, Zareva SY, Nikolova R, Trendafilova E. Synthesis and spectroscopic investigation of (acetylamino)pyridines. Collect. Czech. Chem. Commun. 2009;74:1295–1308.10.1135/cccc2009056
  • Hsu WP. Phase behavior and a modified Kwei equation for ternary polymer blends containing stereoregular PMMA. Thermochim. Acta. 2006;441:137–143.10.1016/j.tca.2005.12.013
  • Slark A. Application of the Kwei equation to the glass transition of dye solute–polymer blends. Polymer. 1999;40:1935–1941.10.1016/S0032-3861(98)00435-2

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.