Combined main-chain/side-chain ionic liquid crystalline polymer based on 'jacketing' effect: Design, synthesis, supra-molecular self-assembly and photophysical properties

Reasonably fabricating ordered structures of ionic polymers is very important for the development of novel func- tional materials. By combining the ions and liquid cry stalline polymer, we successfully designed and synthesized a series of novel combined main-chain/side-chain ionic liquid crystalline polymer (MCSC-ILCPs) containing imidazolium groups and different counter-anions, poly (2,5-bis{(6-(4-butoxy-4!-imidazolium biphenyl)hexyl)oxycarbonyl}styrene salts) poly(BImBHCS-X) with the following types of counter-anions (Br", BF4", PF6" and TFSI"). Combined technologies con- firmed the chemical structures of the monomers and polymers with imidazolium cation and different counter-anions. Dif- ferential scanning calorimetry (DSC), polarized light microscopy (PLM) and one- and two-dimensional wide-angle X-ray diffraction (1D and 2D WAXD) results illustrated that the LC structures and the transitions of ordered structures depended on the nature of the counter-anion employed. The polymers with Br" and BF4" counter-anions exhibited smectic A (SmA) LC behavior below the isotropic temperature. The another one, poly(BImBHCS-TFSI) with the large volume of the TFSI" anion destroyed the packing of the LC ordered structure resulting in an amorphous structure. The photophysical properties of the polymers prepared can be adjusted by tuning the ionic interaction of the polymers by switching the counter-anion.

[1]  Jinhong Yu,et al.  Enhanced thermal and mechanical properties of epoxy composites by mixing thermotropic liquid crystalline epoxy grafted graphene oxide , 2014 .

[2]  M. Maciejewska,et al.  Effect of ionic liquids on the dispersion of zinc oxide and silica nanoparticles, vulcanisation behaviour and properties of NBR composites , 2014 .

[3]  Hailiang Zhang,et al.  Microphase Separation Facilitating and Stabilizing Hierarchical Segment Self-Assembly of Combined Main-Chain/Side-Chain Liquid Crystalline Polymer in Diblock Copolymer , 2013 .

[4]  Hailiang Zhang,et al.  Design, synthesis, and self‐assembly manipulating of polymerized ionic liquids contained imidazolium based on “Jacketing” effect , 2013 .

[5]  B. Tang,et al.  Mesogen jacketed liquid crystalline polyacetylene containing triphenylene discogen: synthesis and phase structure , 2013 .

[6]  Liang Wang,et al.  Transesterification catalyzed by ionic liquids on superhydrophobic mesoporous polymers: heterogeneous catalysts that are faster than homogeneous catalysts. , 2012, Journal of the American Chemical Society.

[7]  Yangping Wen,et al.  Poly(3,4-ethylenedioxythiophene methanol)/ascorbate oxidase/nafion-single-walled carbon nanotubes biosensor for voltammetric detection of Vitamin C , 2012, Chinese Journal of Polymer Science.

[8]  W. Skene,et al.  π-Conjugated Fluorescent Azomethine Copolymers: Opto-Electronic, Halochromic, and Doping Properties , 2012 .

[9]  Robert B. Moore,et al.  Ionic aggregation in random copolymers containing phosphonium ionic liquid monomers , 2012 .

[10]  D. Mecerreyes Polymeric ionic liquids: Broadening the properties and applications of polyelectrolytes , 2011 .

[11]  Y. Elabd,et al.  Anion exchanged polymerized ionic liquids: High free volume single ion conductors , 2011 .

[12]  K. Winey,et al.  Imidazolium Polyesters: Structure–Property Relationships in Thermal Behavior, Ionic Conductivity, and Morphology , 2011 .

[13]  B. Tang,et al.  Synthesis of polyelectrolytic polyacetylene derivatives by quaternization of poly(pyridylacetylene) , 2011 .

[14]  M. Q. Zhang,et al.  Intrinsic fluorescence studies of compatibility in thermoplastic phenol formaldehyde resin / poly(ε-caprolactone) blends , 2011 .

[15]  M. Q. Zhang,et al.  Interfacial adhesion of nanoparticles in polymer blends by intrinsic fluorescence spectra , 2011 .

[16]  Matthew T. Hunley,et al.  Influence of Counteranion on the Thermal and Solution Behavior of Poly(2-(dimethylamino)ethyl methacrylate)-Based Polyelectrolytes , 2010 .

[17]  Takashi Kato From nanostructured liquid crystals to polymer-based electrolytes. , 2010, Angewandte Chemie.

[18]  Cheuk‐Lam Ho,et al.  Synthesis, Light-Emitting, and Two-Photon Absorption Properties of Platinum-Containing Poly(arylene-ethynylene)s Linked by 1,3,4-Oxadiazole Units , 2010 .

[19]  Xing Fan,et al.  Mesogen-jacketed liquid crystalline polymers. , 2010, Chemical Society reviews.

[20]  Hailiang Zhang,et al.  Hierarchical supramolecular ordering with biaxial orientation of a combined main-chain/side-chain liquid-crystalline polymer obtained from radical polymerization of 2-vinylterephthalate. , 2010, Journal of the American Chemical Society.

[21]  W. Jaeger,et al.  Synthetic polymers with quaternary nitrogen atoms—Synthesis and structure of the most used type of cationic polyelectrolytes , 2010 .

[22]  Qian Yang,et al.  A novel mesogen‐jacketed liquid crystalline electroluminescent polymer with both thiophene and oxadiazole in conjugated side chain , 2010 .

[23]  Xiaogong Wang,et al.  Nanomechanical properties of polyaniline and azo polyelectrolyte multilayer films , 2010 .

[24]  M. Antonietti,et al.  Ionic Liquids as Precursors for Nitrogen‐Doped Graphitic Carbon , 2010, Advanced materials.

[25]  M. Firestone,et al.  The Design of Polymeric Ionic Liquids for the Preparation of Functional Materials , 2009 .

[26]  Matthew D. Green,et al.  Designing Imidazole-Based Ionic Liquids and Ionic Liquid Monomers for Emerging Technologies , 2009 .

[27]  H. Ritter,et al.  Polymerizable ionic liquid crystals. , 2009, Macromolecular rapid communications.

[28]  M. Zhang,et al.  Branched quaternary ammonium amphiphiles: nematic ionic liquid crystals near room temperature. , 2009, Chemical communications.

[29]  R. Marcilla,et al.  Pyrrolidinium-based polymeric ionic liquids as mechanically and electrochemically stable polymer electrolytes , 2009 .

[30]  S. Rajendran,et al.  Ionic conduction in poly(vinyl chloride)/poly(ethyl methacrylate)-based polymer blend electrolytes complexed with different lithium salts , 2008 .

[31]  B. Liu,et al.  Effect of Charge Density on Energy‐Transfer Properties of Cationic Conjugated Polymers , 2008 .

[32]  H. Ohno,et al.  Noncovalent approach to one-dimensional ion conductors: enhancement of ionic conductivities in nanostructured columnar liquid crystals. , 2008, Journal of the American Chemical Society.

[33]  T. Swager,et al.  Synthesis and mesomorphic properties of rigid-core ionic liquid crystals. , 2007, Journal of the American Chemical Society.

[34]  H. Ohno,et al.  Self-organization of room-temperature ionic liquids exhibiting liquid-crystalline bicontinuous cubic phases: formation of nano-ion channel networks. , 2007, Journal of the American Chemical Society.

[35]  E. Fábregas,et al.  Sulfonated poly(ether ether ketone), an ion conducting polymer, as alternative polymeric membrane for the construction of anion-selective electrodes , 2007 .

[36]  Bao‐yan Zhang,et al.  Synthesis and mesomorphic properties of side‐chain liquid crystalline ionomers containing sulfonic acid groups , 2007 .

[37]  E. I. Lozinskaya,et al.  Synthesis and ionic conductivity of polymer ionic liquids , 2007 .

[38]  Zhivko Zhelev,et al.  Single quantum dot-micelles coated with silica shell as potentially non-cytotoxic fluorescent cell tracers. , 2006, Journal of the American Chemical Society.

[39]  K. Binnemans Ionic liquid crystals. , 2005, Chemical reviews.

[40]  D. Yamazaki,et al.  Pyrimidine‐Core Extended π‐Systems: General Synthesis and Interesting Fluorescent Properties. , 2005 .

[41]  D. Yamazaki,et al.  Pyrimidine-core extended pi-systems: general synthesis and interesting fluorescent properties. , 2004, Journal of the American Chemical Society.

[42]  Mingwu Shen,et al.  Polyelectrolyte multilayer nanoreactors toward the synthesis of diverse nanostructured materials , 2004 .

[43]  H. Ringsdorf,et al.  Model Considerations and Examples of Enantiotropic Liquid Crystalline Polymers , 2004 .

[44]  Stephen Z. D. Cheng,et al.  Manipulating supramolecular self-assembly via tailoring pendant group size of linear vinyl polymers. , 2003, Journal of the American Chemical Society.

[45]  Bao‐yan Zhang,et al.  Compatibilization by main-chain thermotropic liquid crystalline ionomer of blends of PBT/PP , 2002 .

[46]  H. Ohno,et al.  Layered Ionic Liquids: Anisotropic Ion Conduction in New Self‐Organized Liquid‐Crystalline Materials , 2002 .

[47]  J. J. Cebe,et al.  Main‐chain viologen polymers with organic counterions exhibiting thermotropic liquid‐crystalline and fluorescent properties* , 2002 .

[48]  J. Mikroyannidis,et al.  Blue-Light-Emitting Poly(phenylenevinylene)s with Alkoxyphenyl Substituents: Synthesis and Optical Properties , 2002 .

[49]  J. J. Cebe,et al.  Synthesis and Characterization of Poly(pyridinium salt)s with Organic Counterions Exhibiting Both Thermotropic Liquid-Crystalline and Light-Emitting Properties , 2001 .

[50]  Dimitris Vlassopoulos,et al.  Levels of structure formation in aqueous solutions of anisotropic association colloids consisting of rodlike polyelectrolytes , 2001 .

[51]  H. Ohno,et al.  Synthesis of molten salt-type polymer brush and effect of brush structure on the ionic conductivity , 2001 .

[52]  M. Hara,et al.  Ionic Naphthalene Thermotropic Copolyesters: Enhanced Compressive Properties of Fibers , 2001 .

[53]  G. Wegner,et al.  Hierarchical Structures of a Synthetic Rodlike Polyelectrolyte in Water , 2000 .

[54]  X. Wan,et al.  Synthesis of a New Side-Chain Type Liquid Crystal Polymer Poly[dicyclohexyl vinylterephthalate] , 1999 .

[55]  Makinen,et al.  Switching supramolecular polymeric materials with multiple length scales , 1998, Science.

[56]  R. Bose,et al.  Lyotropic Liquid Crystalline Main-Chain Viologen Polymers: Homopolymer of 4,4`-Bipyridyl with the Ditosylate oftrans-1,4-Cyclohexanedimethanol and Its Copolymers with the Ditosylate of 1,8-Octanediol , 1998 .

[57]  D. Guillon,et al.  Effect of smectogenicity of the ionic groups on the thermotropic liquid crystalline behavior of pyridinium and poly(4-vinylpyridinium) salts quaternized with mesogenic groups , 1997 .

[58]  M. Hara,et al.  Ionic naphthalene thermotropic copolyesters: Effect of ionic content , 1997 .

[59]  T. Uryu,et al.  Structures and Properties of Supramolecular Liquid-Crystalline Side-Chain Polymers Built through Intermolecular Hydrogen Bonds , 1996 .

[60]  V. Percec,et al.  Fluorophobic Effect Induces the Self-Assembly of Semifluorinated Tapered Monodendrons Containing Crown Ethers into Supramolecular Columnar Dendrimers Which Exhibit a Homeotropic Hexagonal Columnar Liquid Crystalline Phase , 1996 .

[61]  R. Jerome,et al.  Synthesis and Preliminary Characterization of Model Liquid Crystalline Ionomers , 1996 .

[62]  P. Bhowmik,et al.  Lyotropic liquid crystalline main‐chain viologen polymers , 1995 .

[63]  Yue Zhao,et al.  Side-Chain Liquid Crystalline Ionomers. 2. Orientation in a Magnetic Field , 1995 .

[64]  C. Bazuin,et al.  Novel Liquid-Crystalline Polymeric Materials via Noncovalent “Grafting” . , 1993 .

[65]  C. Bazuin,et al.  Novel liquid-crystalline polymeric materials via noncovalent grafting: Hydrogen-bonded complexes with poly(4-vinyl pyridine) , 1992 .

[66]  S. Ujiie,et al.  Thermal Properties and Ferroelectric Like Behavior of Liquid-Crystalline Ionic Polyethylenimine Derivative , 1991 .

[67]  Zi-fa Li,et al.  Studies on the post-polymerization of a liquid-crystal polymer with x-shaped mesogens , 1989 .

[68]  V. Percec,et al.  Liquid crystalline polymers containing heterocycloalkanediyl groups as mesogens. 7. Molecular weight and composition effects on the phase transitions of poly(methylsiloxane)s and poly(methylsiloxane-co-dimethylsiloxane)s containing 2-[4-(2(S)-methyl-1-butoxy)phenyl]-5-(11-undecanyl)-1,3,2-dioxaborin , 1989 .

[69]  E. Goethals,et al.  Ion exchange and ring‐opening reactions of telechelic poly(tetrahydrofuran)s containing terminal cyclic quaternary ammonium salts , 1987 .

[70]  Qifeng Zhou,et al.  Synthesis of liquid-crystalline polyacrylates with laterally substituted mesogens , 1987 .

[71]  H. Ringsdorf,et al.  Liquid crystalline polymers with biphenyl-moieties as mesogenic group , 1978 .

[72]  H. Ringsdorf,et al.  Model considerations and examples of enantiotropic liquid crystalline polymers. Polyreactions in ordered systems, 14 , 1978 .