Helical poly(N-propargylamide)s with functional catechol groups: Synthesis and adsorption of metal ions in aqueous solution

Li, Lei; Yan, Lifeng; Luo, Xiaofeng; Deng, Jianping; Yang, Wantai

doi:10.1016/j.reactfunctpolym.2010.09.006

Cited by 31 publications

(17 citation statements)

References 42 publications

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“…The results with respect to UV-Vis absorption spectra are similar to some mono-substituted polyacetylenes studied by us earlier, e.g., poly(N -propargylsulfamide)s [34] and poly(N -propargylurea)s [26]. However, under the investigated conditions, the present poly(N -propargylthiourea)s failed to form helical conformations, which were frequently observed in mono-substituted polyacetylenes [23][24][25]35]. The lacking of ordered helical conformations in the currently studied poly(N -propargylthiourea)s is assumed to be originated in the two -N-H groups of poly(4) in the pendant chains.…”

Section: Uv-vis Spectrum Of M4 and Poly(4)supporting

confidence: 85%

“…Acetylene-based polymers, as typical conjugated polymers, have been extensively investigated by the groups of Masuda [18], Tang [19], Yashima [20], Percec [21] and Aoki [22]. In our earlier studies, a series of mono-substituted polyacetylenes bearing various functional pendent groups have been synthesized, including poly(N -propargylamide)s [23,24], poly(Npropargylsulfamide)s [25] and poly(N -propargylurea) [26]. Taking into consideration of the versatile functional thiourea groups and interesting properties of conjugated polyacetylenes, we expect to design and prepare a novel type of substituted polyacetylenes containing pendent thiourea moieties in the side-chains.…”

Section: Introductionmentioning

confidence: 99%

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A Novel Type of Mono-Substituted Polyacetylene: Synthesis and Characterization of Poly(N-Propargylthiourea)s

Luo

Chang

et al. 2011

Designed Monomers and Polymers

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This article reports for the first time about a novel category of mono-substituted acetylene monomers (1-4, M1-M4) (C≡CCH 2 NHCSNHR, R for M1 = CH 2 CH 3 ; M2 = (CH 2 ) 3 CH 3 ; M3 = (CH 2 ) 5 CH 3 ; M4 = C 6 H 5 ). The four monomers were identified by FT-IR, 1 H-NMR, 13 C-NMR spectroscopy and elementary analysis. In the presence of a rhodium catalyst ((nbd)Rh + B − (C 6 H 5 ) 4 (nbd = 2,5-norbornadiene)), M1-M4 underwent polymerization and provided the expected poly(N-propargylthiourea)s in a moderate to high yield (58-92%) and with a high cis content ( 91%) in the polymer backbones. The substituents had a big influence on the solubility of poly(N-propargylthioureas). Among the four polymers, polymer 4 (poly(4)) showed good solubility and relatively higher number-average molecular weight (up to 12 000). This polymer was further characterized by FT-IR and UV-Vis spectroscopy. TGA analysis demonstrated that the polymer remained stable up to 175 • C. Poly(4) exhibited considerable adsorption ability toward to Fe 3+ ions. The novel substituted polyacetylenes are also expected to exhibit some unique properties, such as inhibition of bacteria, chiral recognition, metal extraction and metal detection, derived from a combination of conjugated polymer backbones and highly functional thiourea groups in the side-chains.

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Section: Uv-vis Spectrum Of M4 and Poly(4)supporting

confidence: 85%

Section: Introductionmentioning

confidence: 99%

A Novel Type of Mono-Substituted Polyacetylene: Synthesis and Characterization of Poly(N-Propargylthiourea)s

Luo

Chang

et al. 2011

Designed Monomers and Polymers

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“…This field is expanding rapidly, especially in the last 5 years, with many laboratories contributing. 24 Mussel mimetic polymers are being generated from polypeptides, 25–27 polyamides, 28 polyacrylates, 17,29–35 polyethylene glycols, 36–52 polystyrenes, 53–59 and polyurethanes. 60 These polymers are enabling the development of imaging agents, 48 nanoparticle shells, 44,48,61 elastomers, 30,33,59 resins, 58,62 coacervates, 31 hydrogels, 36–38,42,43 surface treatments, 27,40,49,52 antibacterial coverings, 51,63 and antifouling coatings.…”

Section: Introductionmentioning

confidence: 99%

Polymer Composition and Substrate Influences on the Adhesive Bonding of a Biomimetic, Cross-Linking Polymer

2012

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Hierarchical biological materials such as bone, sea shells, and marine bioadhesives are providing inspiration for the assembly of synthetic molecules into complex structures. The adhesive system of marine mussels has been the focus of much attention in recent years. Several catechol-containing polymers are being developed to mimic the cross-linking of proteins containing 3,4-dihydroxyphenylalanine (DOPA) used by shellfish for sticking to rocks. Many of these biomimetic polymer systems have been shown to form surface coatings or hydrogels, however bulk adhesion is demonstrated less often. Developing adhesives requires addressing design issues including finding a good balance between cohesive and adhesive bonding interactions. Despite the growing number of mussel mimicking polymers, there has been little effort to generate structure-property relations and gain insights on what chemical traits give rise to the best glues. In this report, we examined the simplest of these biomimetic polymers, poly[(3,4-dihydroxystyrene)-co-styrene]. Pendant catechol groups (i.e., 3,4-dihydroxystyrene) were distributed throughout a polystyrene backbone. Several polymer derivatives were prepared, each with a different 3,4-dihyroxystyrene content. Bulk adhesion testing showed where the optimal middle ground of cohesive and adhesive bonding resides. Adhesive performance was benchmarked against commercial glues as well as the genuine material produced by live mussels. In the best case, bonding was similar to cyanoacrylate “Krazy” or “Super” glue. Performance was also examined using low (e.g., plastics) and high (e.g., metals, wood) energy surfaces. Adhesive bonding of poly[(3,4-dihydroxystyrene)-co-styrene] may be the strongest of reported mussel protein mimics. These insights should help us to design future biomimetic systems, thereby bringing us closer to development of bone cements, dental composites, and surgical glues.

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“…The synthesis of three monomers (M1ÀM3) and the related results were reported in the preceding papers [33,37,38]. To prepare the helical macromonomers, all the copolymerizations were carried out with (nbd)Rh + B À (C 6 H 5 ) 4 as a catalyst in dry CHCl 3 at 30°C for 3 h. To exclude the effects of oxygen, the monomer solution and catalyst solution were prepared first and then bubbled with nitrogen for 20 min.…”

Section: Synthesis Of Monomers and Helical Macromonomersmentioning

confidence: 99%

“…In this present study, catechol groups are incorporated into the designed helical copolymer to improve the adsorption capability of the hydrogels [34][35][36]. The helical copolymers were prepared from three monomers (M1ÀM3), in which M1 introduces the catechol functional groups [37], M2 introduces the polymerizable C@C groups, and M3 offers helical chain segments along the polymer backbones [38]. Moreover, PEGs were used to introduce macropores within the hydrogels.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of optically active macroporous poly(N-isopropylacrylamide) hydrogels with helical poly(N-propargylamide) for chiral recognition of amino acids

Helical poly(N-propargylamide)s with functional catechol groups: Synthesis and adsorption of metal ions in aqueous solution

Cited by 31 publications

References 42 publications

A Novel Type of Mono-Substituted Polyacetylene: Synthesis and Characterization of Poly(N-Propargylthiourea)s

A Novel Type of Mono-Substituted Polyacetylene: Synthesis and Characterization of Poly(N-Propargylthiourea)s

Polymer Composition and Substrate Influences on the Adhesive Bonding of a Biomimetic, Cross-Linking Polymer

Synthesis of optically active macroporous poly(N-isopropylacrylamide) hydrogels with helical poly(N-propargylamide) for chiral recognition of amino acids

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