SYNTHESIS AND PROPERTIES OF CROSS-LINKED POLYMERS CONTAINING DIARYLBIBENZOFURANONE BY ADMET POLYMERIZATION
|
|
- Marybeth Daniels
- 6 years ago
- Views:
Transcription
1 SYNTHESIS AND PROPERTIES OF CROSS-LINKED POLYMERS CONTAINING DIARYLBIBENZOFURANONE BY ADMET POLYMERIZATION T. Ohishi, 1 K. Imato, 2 T. Kanehara, 2 A. Takahara, 1,2 and H. Otsuka 1,2 1 Institute for Materials Chemistry and Engineering, Kyushu University, 2 Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka , Japan - t-ohishi@cstf.kyushu-u.ac.jp Keywords: dynamic covalent bonds, cross-linked polymers, acyclic diene metathesis polymerization ABSTRACT Diarylbibenzofuranone (DABBF) derivatives can be reversibly cleaved to the corresponding arylbenzofuranone (ABF) radicals under mild conditions. We recently reported the synthesis and physicochemical properties of the cross-linked polyurethane containing DABBF unit. The autonomous structural transformation and the macroscopic self-healing of separated gel pieces under air at room temperature without any stimuli were accomplished by a dynamic covalent approach. Since the self-healing property was derived from DABBF units, one can expect the self-healing of DABBF-containing cross-linked polymers with various structures. We here report the acyclic diene metathesis (ADMET) polymerization of multifunctional olefin monomers containing DABBF unit. This is because a low-polarity olefin polymer can be obtained by ADMET polymerization. The DABBF-diolefin monomer was first polymerized at room temperature in the presence of Grubbs catalyst (2nd generation) in CH 2 Cl 2. However, the yield of the obtained polymer was low (29%). Under this condition, it is considered that the ethylene molecules produced during polymerization can not be removed. The polymerization was also performed at 40 C to give polymers in good yield (83%). Furthermore, cross-linked polymers were synthesized by ADMET polymerization of DABBF-tetraolefin monomer and copolymerization of DABBF-bifunctional olefin monomer and triolefin monomer. All cross-linked polymers were obtained in good yields. These polymers showed high swelling properties in organic solvents with relatively low polarity. 1. INTRODUCTION A reversible system can repeat the self-healing process for numerous cycles when noncovalent bonds or dynamic covalent bonds are used. 1 Such noncovalent and dynamic covalent bonding 2 can be reversed under equilibrium controls. Modified by external stimuli or through continuous component exchange, noncovalent and dynamic covalent bonds can be reorganized or reshuffled to cure the system. Diarylbibenzofuranone (DABBF), a dimer of arylbenzofuranone, exists as a state of equilibrium between dissociation and association and its central C-C bond can act as a dynamic covalent bond at room temperature. 3 We recently reported the synthesis and physicochemical properties of the cross-linked polyurethane containing DABBF 355
2 unit. 4 The autonomous structural transformation and the macroscopic self-healing of separated gel pieces under air at room temperature without any stimuli were accomplished by a dynamic covalent approach. Since the self-healing property was derived from DABBF units, one can expect the self-healing of DABBF-containing cross-linked polymers with various structures. We here report the acyclic diene metathesis (ADMET) polymerization of multifunctional olefin monomers containing DABBF unit. This is because a low-polarity olefin polymer can be obtained by ADMET polymerization. 2. MATERIALS Grubbs second-generation catalyst was purchased from Aldrich. Substrates and reagents were purchased form Tokyo chemical industry or Wako pure chemical industries; 4-hydroxymanderic acid monohydrate, 2,4-di-tert-butylphenol, methane sulfonic acid, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, di-tert-butyl peroxide, 10-undecenoyl chloride, and 1,1,1-tris(4-hydroxyphenyl)ethane were used as supplied. Organic solvents were purchased from Kanto chemical or Wako pure chemical industries at the highest purity and used as supplied. DABBF-diol and DABBF-tetraol were prepared according to the literature. 4 The olefin groups were then introduced by condensation of DABBF-diol and/or DABBF-tetraol 10- undecenoyl chloride at room temperature. This reaction gave the monomers 1 or 2 in high yield (Scheme 1). 3.METHODS Polymerization: An example of the procedure for the synthesis of polymer containing DABBF unit is as follows. In a nitrogen-filled Schlenk flask, Grubbs secondgeneration catalyst was added to the solution of monomer 1 in CH 2 Cl 2, which was degassed with three freeze-vacuum-thaw cycles. Then the mixture was heated to 40 C and stirred for 24 h. The reaction was quenched by adding ethyl vinyl ether using syringe and stirred for 12 h at room temperature. CH 2 Cl 2 was added to the reaction mixture and treated with tris(hydroxymethyl)phosphine (THP) in order to remove the residual catalyst. The polymer was purified by reprecipitation from 356
3 methanol. 1 H NMR (400 MHz) spectroscopic measurements were carried out at 25 C with a 400 MHz Bruker spectrometer using tetramethylsilane (TMS) as internal standard in chloroform-d (CDCl 3 ). Gel permeation chromatographic (GPC) measurements were carried out at 40 C on TOSOH HLC-8220 GPC system equipped with a guard column (TOSOH TSK guard column Super H-L), three columns (TOSOH TSK gel SuperH 6000, 4000, and 2500) and a UV-Vis detector. Tetrahydrofuran (THF) was used as the eluent at a flow rate of 0.6 ml min -1. Polystyrene (PS) standards (M n = ; M w /M n = ) were used to calibrate the GPC system. 4. RESULTS AND DISCUSSION ADMET polymerization of multifunctional olefin monomers containing DABBF The DABBF-diolefin monomer was first polymerized at room temperature in the presence of Grubbs catalyst (2nd generation) in CH 2 Cl 2. However, the yield of the obtained polymer was low (29%). Under this condition, it is considered that the ethylene molecules produced during polymerization can not be removed. The polymerization was also performed at 40 C to give the corresponding polymers in good yield (83%) (Scheme 2). Synthesis and properties of cross-linked polymers containing DABBF Diverse types of cross-linked polymers were synthesized by ADMET polymerization of DABBF-tetraolefin monomer and copolymerization of DABBF-bifunctional olefin monomer and triolefin monomer (Scheme 3). The swelling behavior of the crosslinked polymers containing DABBF was investigated in various organic solvents (Table 1). The cross-linked copolymers containing monomer 1 unit, such as poly1-copoly3 and poly1-co-poly3-co-poly4, did not form a gel in benzene, THF, CHCl 3, and anisole. These results indicates that cross-linked copolymers containing monomer 1 357
4 have low crosslink density. In contrast, the cross-linked copolymers containing monomer 2 unit, such as poly2-co-poly3, poly2-co-poly4, and poly2-co-poly3-copoly4, swelled and absorbed benzene, THF, CHCl 3, and anisole. Accordingly, the swelling properties of these cross-linked copolymer containing DABBF unit are probably dependent on the cross-linked density. Furthermore, poly2-co-poly4 and poly2-co-poly3-co-poly4 were formed high viscosity solution in low-polar organic solvent such as CH 2 Cl 2. These results imply that swelling behavior of cross-linked copolymers containing DABBF unit depends on polymer main chain polarity and dynamic covalent bond property of DABBF unit. 5. CONCLUSIONS We have demonstrated the synthesis and properties of cross-linked polymers having DABBF prepared by ADMET polymerization. All cross-linked polymers were synthesized by ADMET polymerization of DABBF-tetraolefin monomer and copolymerization of DABBF-bifunctional olefin monomer and triolefin monomer. These polymers showed high swelling properties in organic solvents with relatively low polarity. Furthermore, poly2-co-poly4 and poly2-co-poly3-co-poly4 were formed high viscosity solution in low-polar organic solvent. These results imply that swelling behavior of cross-linked copolymers containing DABBF unit depends on polymer main chain polarity and dynamic covalent bond property of DABBF unit. ACKNOWLEDGEMENTS The authors gratefully acknowledge the financial support of the Funding Program (Green Innovation GR077) for Next Generation World-Leading Researchers from the Cabinet Office, Government of Japan. REFERENCES [1] Syrett, J. A.; Becer, C. R.; Haddleton, D. M. Polym. Chem. 2010, 1, [2] (a) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, (b) Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J. L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, (c) Lehn, J. M. Chem. Soc. Rev. 2007, 36,
5 [3] Frenette, M.; Maclean, P. D.; Barclay, L. R. C.; Scaiano, J. C. J. Am. Chem. Soc., 2006, 128, [4] Imato, K.; Nishihara, M.; Kanehara, T.; Amamoto, Y.; Takahara, A.; Otsuka, H. Angew. Chem. Int. Ed., 2012, 51,
Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008
Supplementary Information for: Scrambling Reaction between Polymers Prepared by Step-growth and Chain-growth Polymerizations: Macromolecular Cross-metathesis between 1,4-Polybutadiene and Olefin-containing
More informationPolymer Inorganic Composites with Dynamic Covalent Mechanochromophore
Supporting Information Polymer Inorganic Composites with Dynamic Covalent Mechanochromophore Takahiro Kosuge,, Keiichi Imato, Raita Goseki,, and Hideyuki tsuka*,, Department of rganic and Polymeric Materials,
More informationSupporting Information for
Supporting Information for AmPhos Pd-Catalyzed Suzuki-Miyaura Catalyst-Transfer Condensation Polymerization: Narrower Dispersity by Mixing the Catalyst and Base Prior to Polymerization Kentaro Kosaka,
More informationChemically recyclable alternating copolymers with low polydispersity from
Electronic Supplementary Information Chemically recyclable alternating copolymers with low polydispersity from conjugated/aromatic aldehydes with vinyl ethers: selective degradation to another monomer
More informationSupporting Information
Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of Poly(dihydroxystyrene-block-styrene) (PDHSt-b-PSt) by the RAFT
More informationBlending conjugated polymers without phase separation for fluorescent colour tuning of polymeric materials through FRET
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary Information Blending conjugated polymers without phase separation for fluorescent
More informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Cis-Selective Ring-Opening Metathesis Polymerization with Ruthenium Catalysts Benjamin K. Keitz, Alexey Fedorov, Robert H. Grubbs* Arnold and Mabel Beckman Laboratories of Chemical
More informationSupporting Information
Supporting Information Branched polyethylene mimicry by metathesis copolymerization of fatty acid-based α,ω-dienes. Thomas Lebarbé, a,b,d Mehdi Neqal, a,b Etienne Grau, a,b Carine Alfos, c and Henri Cramail
More informationSupporting information
Supporting information Temperature and ph-dual Responsive AIE-Active Core Crosslinked Polyethylene Poly(methacrylic acid) Multimiktoarm Star Copolymers ` Zhen Zhang,*,, and Nikos Hadjichristidis*, School
More informationA novel smart polymer responsive to CO 2
A novel smart polymer responsive to CO 2 Zanru Guo, a,b Yujun Feng,* a Yu Wang, a Jiyu Wang, a,b Yufeng Wu, a,b and Yongmin Zhang a,b a Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences,
More informationSupporting Information. Sequence-Regulated Copolymers via Tandem Catalysis of Living Radical Polymerization and In Situ Transesterification
Supporting Information Sequence-Regulated Copolymers via Tandem Catalysis of Living Radical Polymerization and In Situ Transesterification Kazuhiro Nakatani, Yusuke Ogura, Yuta Koda, Takaya Terashima*,
More informationNOTE KAZUO YOSHINO, AKIHIRO YOKOYAMA, TSUTOMU YOKOZAWA
NOTE Well-Defined Star-Shaped Poly(p-benzamide) via Chain-Growth Condensation Polymerization: Use of Tetra-Functional Porphyrin Initiator to Optimize Star Polymer Formation KAZUO YOSHINO, AKIHIRO YOKOYAMA,
More informationOptimizing Ion Transport in Polyether-based Electrolytes for Lithium Batteries
Supporting Information Optimizing Ion Transport in Polyether-based Electrolytes for Lithium Batteries Qi Zheng, 1 Danielle M. Pesko, 1 Brett M. Savoie, Ksenia Timachova, Alexandra L. Hasan, Mackensie C.
More informationAziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize
More informationSUPPLEMENTARY INFORMATION
DOI: 10.1038/NCHEM.2633 Mechanically controlled radical polymerization initiated by ultrasound Hemakesh Mohapatra, Maya Kleiman, Aaron P. Esser-Kahn Contents 1. Materials and methods 2 2. Procedure for
More informationSupplementary Information. chemical-shift change upon binding of calcium ion
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary Information for Design of a hyperpolarized 15 N NMR probe that induces a large chemical-shift
More informationHelix Formation of Poly(phenylacetylene)s Bearing Azide Groups through Click Polymer Reaction with Optically Active Acetylenes
Supporting Information Helix Formation of Poly(phenylacetylene)s earing Azide Groups through Click Polymer Reaction with Optically Active Acetylenes Ken Itomi, Shinzo Kobayashi, Kazuhide Morino, Hiroki
More informationOne-pot polymer brush synthesis via simultaneous isocyanate coupling chemistry and grafting from RAFT polymerization
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 One-pot polymer brush synthesis via simultaneous isocyanate coupling chemistry and grafting
More informationAll-conjugated, all-crystalline donor-acceptor block. copolymers P3HT-b-PNDIT2 via direct arylation
upporting information for All-conjugated, all-crystalline donor-acceptor block copolymers P3HT-b-PNDIT2 via direct arylation polycondensation Fritz Nübling,, Hartmut Komber, Michael ommer,, Makromolekulare
More informationSynthesis of hydrophilic monomer, 1,4-dibromo-2,5-di[4-(2,2- dimethylpropoxysulfonyl)phenyl]butoxybenzene (Scheme 1).
Supporting Information Materials. Hydroquinone, potassium carbonate, pyridine, tetrahydrofuran (THF for organic synthesis) were purchased from Wako Pure Chemical Industries Ltd and used as received. Chlorosulfuric
More informationSupplementary Material for
www.sciencemag.org/content/343/6173/873/suppl/dc1 Supplementary Material for Nonswellable Hydrogel Without Mechanical Hysteresis Hiroyuki Kamata, Yuki Akagi, Yuko Kayasuga-Kariya, Ung-il Chung, Takamasa
More informationSupporting Information
Supporting Information Z-Selective Homodimerization of Terminal Olefins with a Ruthenium Metathesis Catalyst Benjamin K. Keitz, Koji Endo, Myles B. Herbert, Robert H. Grubbs* Arnold and Mabel Beckman Laboratories
More informationSupporting Information
Supporting Information Molecular Weight Dependence of Zero-Shear Viscosity in Atactic Polypropylene Bottlebrush Polymers Samuel J. Dalsin, Marc A. Hillmyer,*, and Frank S. Bates*, Department of Chemical
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information (ESI) Tetraarylsuccinonitriles as Mechanochromophores to Generate
More informationMolecular Weight Distribution of Living Chains in Polystyrene Pre-pared by Atom Transfer Radical Polymerization
Molecular Weight Distribution of Living Chains in Polystyrene Pre-pared by Atom Transfer Radical Polymerization Joongsuk Oh, a Jiae Kuk, a Taeheon Lee, b Jihwa Ye, b Huyn-jong Paik, b* Hyo Won Lee, c*
More informationDouble-decker-shaped Silsesquioxane Having
Supporting Information Hydrosilylation Polymerization of Double-decker-shaped Silsesquioxane Having Hydrosilane with Diynes Makoto Seino, Teruaki Hayakawa, Yoshihito Ishida, and Masa-aki Kakimoto* Department
More informationPhoto-Cleavage of Cobalt-Carbon Bond: Visible. Light-Induced Living Radical Polymerization Mediated by. Organo-Cobalt Porphyrins
Photo-Cleavage of Cobalt-Carbon Bond: Visible Light-Induced Living Radical Polymerization Mediated by Organo-Cobalt Porphyrins Yaguang Zhao, Mengmeng Yu, and Xuefeng Fu* Beijing National Laboratory for
More informationTunable thermo-responsive water-dispersed multi walled. carbon nanotubes
Tunable thermo-responsive water-dispersed multi walled carbon nanotubes Gaojian Chen, Peter M. Wright, Jin Geng, Giuseppe Mantovani, and David M. Haddleton* Department of Chemistry, University of Warwick,
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationOne polymer for all: Benzotriazole Containing Donor-Acceptor Type Polymer as a Multi-Purpose Material
One polymer for all: Benzotriazole Containing Donor-Acceptor Type Polymer as a Multi-Purpose Material Abidin Balan a, Derya Baran a, Gorkem Gunbas a,b, Asuman Durmus a,b, Funda Ozyurt a and Levent Toppare
More informationAtom transfer radical polymerization (ATRP) of styrene and methyl methacrylate with a,a-dichlorotoluene as initiator; a kinetic study
980 Macromol. Chem. Phys. 201, 980 984 (2000) Full Paper: The atom transfer radical polymerization (ATRP) of styrene and methyl methacrylate with a,adichlorotoluene (DCT) as initiator results in the respective
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Nanoparticle-to-vesicle and nanoparticle-to-toroid transitions of ph-sensitive
More informationSynthesis and Radical Polymerization Behavior of Bifunctional Vinyl Monomer Derived from N-Vinylacetamide and p-chloromethylstyrene
Synthesis and Radical Polymerization Behavior of Bifunctional Vinyl Monomer Derived from N-Vinylacetamide and p-chloromethylstyrene TAKERU IWAMURA,* TOMOYUKI NAKAGAWA, TAKESHI ENDO Research Laboratory
More informationLiquid marbles as a micro-reactor for efficient radical alternating copolymerisation of diene monomer and oxygen
Electronic Supplementary Material (ESI) for ChemComm. This journal is The oyal Society of Chemistry 2015 Electronic Supplementary Information for Chemical Communications Liquid marbles as a micro-reactor
More informationSynthesis and characterization of amino-functionalized Poly(propylene carbonate)
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supplementary Information Synthesis and characterization of amino-functionalized Poly(propylene
More informationMild and efficient bromination of Poly(hydroxyethyl)acrylate and its use towards Ionic-Liquid containing polymers
Supporting Information for Mild and efficient bromination of Poly(hydroxyethyl)acrylate and its use towards Ionic-Liquid containing polymers Vinu Krishnan Appukuttan, Anais Dupont, Sandrine Denis-Quanquin,
More informationEffect of Molecular Structure of Side Chain Polymers on "Click" Synthesis of Thermosensitive Molecular Brushes
University of Tennessee, Knoxville Trace: Tennessee Research and Creative Exchange University of Tennessee Honors Thesis Projects University of Tennessee Honors Program 5-2017 Effect of Molecular Structure
More informationOne-Shot Synthesis and Melt Self-Assembly of Bottlebrush Copolymers with a Gradient Compositional Profile
One-Shot Synthesis and Melt Self-Assembly of Bottlebrush Copolymers with a Gradient Compositional Profile Liuyin Jiang, Dmytro Nykypanchuk, Alexander Ribbe and Javid Rzayev* Department of Chemistry, University
More informationHigh Molecular Weight Bile Acid and Ricinoleic Acid-Based Co-polyesters via Entropy-Driven Ring-Opening Metathesis Polymerisation
High Molecular Weight Bile Acid and Ricinoleic Acid-Based Co-polyesters via Entropy-Driven Ring-Opening Metathesis Polymerisation Julien E. Gautrot, X.X. Zhu * Département de Chimie, Université de Montréal,
More informationSolvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
More informationSupporting Information for
Supporting Information for Chelated Ruthenium Catalysts for Z-Selective Olefin Metathesis Koji Endo and Robert H. Grubbs* Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry
More informationSupporting Information
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Photochemical Regulation of a Redox-Active Olefin Polymerization
More informationEfficient Magnesium Catalysts for the Copolymerization of Epoxides and CO 2 ; Using Water to Synthesize Polycarbonate Polyols
Supporting Information for Efficient Magnesium Catalysts for the Copolymerization of Epoxides and CO 2 ; Using Water to Synthesize Polycarbonate Polyols Michael R. Kember, Charlotte K. Williams* Department
More informationEnantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition
More informationSupplementary Information. Rational Design of Soluble and Clickable Polymers Prepared by. Conventional Free Radical Polymerization of
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supplementary Information Rational Design of Soluble and Clickable Polymers Prepared by
More informationSupporting Information
Supporting Information A Rational Design of Highly Controlled Suzuki-Miyaura Catalyst-Transfer Polycondensation for Precision Synthesis of Polythiophenes and their Block Copolymers: Marriage of Palladacycle
More informationSupporting Information
Supporting Information Solid Polymer Electrolytes Based on Functionalized Tannic Acids from Natural Resources for All-Solid-State Lithium- Ion Batteries Jimin Shim, [a] Ki Yoon Bae, [b] Hee Joong Kim,
More informationA Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
More informationNovel Supercapacitor Materials Including OLED emitters
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015 Supporting Information Novel
More informationAcid-Base Bifunctional Shell Cross-Linked Micelle Nanoreactor for One-pot Tandem Reaction
Supporting Information Acid-Base Bifunctional Shell Cross-Linked Micelle Nanoreactor for One-pot Tandem Reaction Li-Chen Lee, a# Jie Lu, b# Marcus Weck, b * Christopher W. Jones a * a School of Chemical
More informationZwitterionic Polymerization: A Kinetic Strategy for the Controlled Synthesis of Cyclic Polylactide
SUPPORTING INFORATION Zwitterionic Polymerization: A Kinetic Strategy for the Controlled Synthesis of Cyclic Polylactide Wonhee Jeong, Eun Ji Shin, Darcy A. Culin,, James L. Hedric, and Robert. Waymouth,*
More informationELECTRONIC SUPPORTING INFORMATION Pentablock star shaped polymers in less than 90 minutes via
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 ELECTRONIC SUPPORTING INFORMATION Pentablock star shaped polymers in less than 90 minutes
More informationSupporting Information. Copolymers of Tetrahydrofuran and Epoxidized Vegetable Oils: Application to Elastomeric Polyurethanes
Supporting Information Copolymers of Tetrahydrofuran and Epoxidized Vegetable Oils: Application to Elastomeric Polyurethanes Andrew J Clark,* Seng Soi Hoong Department of Chemistry, University of Warwick,
More informationHighly Luminescent -Conjugated Dithienometalloles: Photophysical Properties and Application to Organic Light-Emitting Diodes
Electronic Supplementary Information (ESI) Highly Luminescent -Conjugated Dithienometalloles: Photophysical Properties and Application to Organic Light-Emitting Diodes Ryosuke Kondo, a Takuma Yasuda,*
More informationLight irradiation experiments with coumarin [1]
Materials and instruments All the chemicals were purchased from commercial suppliers and used as received. Thin-layer chromatography (TLC) analysis was carried out on pre-coated silica plates. Column chromatography
More informationHyperbranched Poly(N-(2-Hydroxypropyl) Methacrylamide) via RAFT Self- Condensing Vinyl Polymerization
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2016 Hyperbranched Poly(N-(2-Hydroxypropyl) Methacrylamide) via RAFT Self- Condensing Vinyl
More informationAir-Stable (Phenylbuta-1,3-diynyl)palladium(II) Complexes: Highly Active Initiators for Living Polymerization of Isocyanides
Supporting Information Air-Stable (Phenylbuta-1,3-diynyl)palladium(II) Complexes: Highly Active Initiators for Living Polymerization of Isocyanides Ya-Xin Xue, Yuan-Yuan Zhu, Long-Mei Gao, Xiao-Yue He,
More informationSupporting Information
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information A synthetic strategy for the preparation of sub-100nm functional
More informationEngineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto , Japan. Contents
Synthesis of Helical Rod/Coil Multiblock Copolymers by Living Block Copolymerization of Isocyanide and o-diisocyanobenzene by Using Arylnickel Initiators Tetsuya Yamada, a and Michinori Suginome * a a
More informationCationic scandium aminobenzyl complexes. synthesis, structure, and unprecedented catalysis of copolymerization of 1-hexene and dicyclopentadiene
Cationic scandium aminobenzyl complexes. synthesis, structure, and unprecedented catalysis of copolymerization of 1-hexene and dicyclopentadiene Xiaofang Li, Masayoshi Nishiura, Kyouichi Mori, Tomohiro
More informationXiangxiong Chen, Mohd Yusuf Khan and Seok Kyun Noh* School of Chemical Engineering, Yeungnam University, Dae-dong, Gyeongsan,
Electronic Supplementary Information For M Amount of Fe (III)-mediated ATR of MMA with hosphorus Containing Ligands in the Absence of Any Additives Xiangxiong Chen, Mohd Yusuf Khan and Seok Kyun Noh* School
More informationSupporting Information. Synthesis of Sulfur-Rich Polymers: Copolymerization of Episulfide with Carbon Disulfide
upporting Information ynthesis of ulfur-rich Polymers: Copolymerization of Episulfide with Carbon Disulfide by Using [PPN]/(salph)(III) ystem Koji Nakano, Go Tatsumi and Kyoko Nozaki* Department of Chemistry
More informationTuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts
More informationSupporting Information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 217 Electronic Supplementary Material
More informationSupporting Information
Supporting Information UCST or LCST? Composition-Dependent Thermoresponsive Behavior of Poly(N-Acryloylglycinamide-co-Diacetone Acrylamide) Wenhui Sun, Zesheng An*, Peiyi Wu * Experimental Materials Glycinamide
More informationSupporting Information for
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for
More informationAutonomous Fluorescence Regulation in Responsive Polymer Systems Driven by a Chemical Oscillating Reaction **
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2016 Electronic Supporting Information Autonomous Fluorescence Regulation in Responsive Polymer
More informationSpin Capturing with Nitrones: Radical Coupling Reactions with Concurrent Introduction of Midchain Functionality
Supplementary Information: Spin Capturing with Nitrones: Radical Coupling Reactions with Concurrent Introduction of Midchain Functionality Edgar H. H. Wong, a,b Cyrille Boyer, b Martina H. Stenzel, b Christopher
More informationSupplementary Materials: SRG Inscription in Supramolecular Liquid Crystalline Polymer Film: Replacement of Mesogens
Supplementary Materials: SRG Inscription in Supramolecular Liquid Crystalline Polymer Film: Replacement of Mesogens Shun Mitsui, Mitsuo Hara, Shusaku Nagano, and Takahiro Seki S. Synthesis Materials Sodium
More informationInduced Circular Dichroism of Stereoregular Vinyl Polymers
Induced Circular Dichroism of Stereoregular Vinyl Polymers Lung-Chi Chen, Yung-Cheng Mao, Shih-Chieh Lin, Ming-Chia Li, Rong-Ming Ho*, Jing-Cherng Tsai* Supplementary Information Figure S1. 13 C NMR (125
More informationSupporting Information
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information RAFT-mediated, Visible Light-initiated Single Unit Monomer Insertion
More informationElectronic Supplementary Information. for. Self-Assembly of Dendritic-Linear Block Copolymers With Fixed Molecular Weight and Block Ratio.
Electronic Supplementary Information for Self-ssembly of Dendritic-Linear lock Copolymers With Fixed Molecular Weight and lock Ratio Moon Gon Jeong, a Jan C. M. van Hest, b Kyoung Taek Kim a, * a School
More informationSupplementary Information. "On-demand" control of thermoresponsive properties of poly(n-isopropylacrylamide) with cucurbit[8]uril host-guest complexes
upplementary Information "n-demand" control of thermoresponsive properties of poly(n-isopropylacrylamide) with cucurbit[8]uril host-guest complexes Urs Rauwald, Jesús del Barrio, Xian Jun Loh, and ren
More informationSupporting Information
Supporting Information Solid-state Conversion of Processable 3,4-Ethylenedioxythiophene (EDOT) Containing Poly(arylsilane) Precursors to π-conjugated Conducting Polymers Jayesh G. Bokria, Arvind Kumar,
More informationWell-defined polyethylene-based random, block and bilayered molecular cobrushes
Well-defined polyethylene-based random, block and bilayered molecular cobrushes Hefeng Zhang, 1,2 Zhen Zhang, 1,2 Yves Gnanou, 2 Nikos Hadjichristidis 1,2 * King Abdullah University of Science and Technology
More informationSupporting Information
Supporting Information New Catalytic Insights Into Acid/Base Conjugates: Highly Selective Bifunctional Catalysts for the Ring-Opening Polymerization of Lactide Daniel J. Coady, Kazuki Fukushima, Hans W.
More informationLiving polymerization of arylisocyanide initiated by phenylethynyl palladium(ii) complex
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 214 Supporting Information Living polymerization of arylisocyanide initiated by phenylethynyl
More informationSupporting Information for. Near infrared-to-blue photon upconversion by exploiting direct. S-T absorption of a molecular sensitizer
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2017 Supporting Information for Near infrared-to-blue photon upconversion by
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany A Distinctive Organocatalytic Approach to Complex Macromolecular Architectures Olivier Coulembier, Matthew 5. 5iesewetter, Andrew Mason, Philippe
More informationRAFT /MADIX polymerization of N-vinylcaprolactam in water-ethanol solvent mixtures
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting information for RAFT /MADIX polymerization of N-vinylcaprolactam in water-ethanol
More informationRAFT and Click Chemistry : A Versatile Approach to the Block Copolymer Synthesis
RAFT and Click Chemistry : A Versatile Approach to the Block Copolymer ynthesis Damien Quémener, Thomas P. Davis, Christopher Barner-Kowollik* and Martina H. tenzel* Centre for Advanced Macromolecular
More informationLigand-free coupling of phenols and alcohols with aryl halides by a recyclable heterogeneous copper catalyst
Supporting Information Ligand-free coupling of phenols and alcohols with aryl halides by a recyclable heterogeneous copper catalyst Man Wang, Bizhen Yuan, Tongmei Ma, Huanfeng Jiang and Yingwei Li* School
More informationSynthesis and Characterization of Poly [2-(3,7- dimethyloctyloxy)-5-methoxy-p-phenylenevinylene] (MDMO-PPV) by Gilch Polymerization
International Journal of Chemistry and Chemical Engineering. ISSN 2248-9924 Volume 3, Number 2 (2013), pp. 89-94 Research India Publications http://www.ripublication.com Synthesis and Characterization
More informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Polymerization-induced Self-Assembly of Homopolymer and Diblock copolymer: A Facile Approach for preparing Polymer Nano-objects with Higher Order Morphologies Jianbo Tan *a,b, Chundong
More informationBlock copolymers containing organic semiconductor segments by RAFT polymerization
Block copolymers containing organic semiconductor segments by RAFT polymerization Ming Chen, Matthias Häussler, Graeme Moad, Ezio Rizzardo Supplementary Material Radical polymerizations in the presence
More informationProbing Side Chain Dynamics of Branched Macromolecules by Pyrene Excimer Fluorescence INTRODUCTION EXPERIMENTALS
Probing Side Chain Dynamics of Branched Macromolecules by Pyrene Ecimer Fluorescence Shiva Farhangi, Jean Duhamel Institute for Polymer Research, Waterloo Institute of Nanotechnology, Department of Chemistry,
More informationCationic Alkylaluminum-Complexed Zirconocene Hydrides as Participants in Olefin-Polymerization Catalysis. Supporting Information
Cationic Alkylaluminum-Complexed Zirconocene Hydrides as Participants in Olefin-Polymerization Catalysis Steven M. Baldwin, John E. Bercaw, *, and Hans H. Brintzinger*, Contribution from the Arnold and
More informationSupporting Information
Supporting Information Rhodium-Catalyzed Annulation Reactions of 2-Cyanophenylboronic Acid with Alkynes and Strained Alkenes Tomoya Miura and Masahiro Murakami* Department of Synthetic Chemistry and Biological
More informationSupporting Information
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Boron Stitching Reaction: A Powerful Tool for the Synthesis of
More informationFormal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis
Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,
More informationSupplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric
Supplementary Information for Stable Supramolecular Helical Structure of C 6 -Symmetric Hydrogen-Bonded Hexakis(phenylethynyl)benzene Derivatives with Amino Acid Pendant Groups and Their Unique Fluorescence
More informationSupporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis** Myles B. Herbert, Vanessa M. Marx, Richard L. Pederson, and Robert
More informationSupporting information. for. hydrophobic pockets for acylation reactions in water
Supporting information for Functionalized organocatalytic nanoreactors: hydrophobic pockets for acylation reactions in water Pepa Cotanda, Annhelen Lu, Joseph P. Patterson, Nikos Petzetakis, Rachel K.
More informationFree radical and RAFT polymerization of vinyl
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Free radical and RAFT polymerization of vinyl esters
More informationSalan ligands assembled around chiral bipyrrolidine: predetermination of chirality around octahedral Ti and Zr. centres
Electronic Supplementary Information for: Salan ligands assembled around chiral bipyrrolidine: predetermination of chirality around octahedral Ti and Zr centres Ekaterina Sergeeva, Jacob Kopilov, Israel
More informationSupporting Information
Supporting Information Facile polyisobutylene functionalization via thiol-ene Click chemistry Andrew J. D. Magenau, Justin W. Chan, Charles E. Hoyle, and Robson F. Storey School of Polymers and High Performance
More informationElectronic Supplementary Information. Water-Soluble Aromatic Polyamide for New Polymer Hydrogelator with Thixotropic Nature
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Water-Soluble Aromatic Polyamide for New Polymer Hydrogelator
More informationSupporting Information
Supporting Information Supramolecular design for polymer/titanium oxo-cluster hybrids: An open door to new organic-inorganic dynamers Fabien Périneau, Sandrine Pensec, Clément Sanchez, Costantino Creton,
More informationSupporting Information
Copyright WILEY-VCH Verlag GmbH & Co. KGaA, 69469 Weinheim, Germany, 2012. Supporting Information for Macromol. Rapid Commun., DOI: 10.1002/marc.201200096 Chain-growth Polymerization of Aryl Grignards
More information