Self-Assembling of an Amphiphilic Polyacetylene Carrying <scp>l</scp>-Leucine Pendants:  A Homopolymer Case

Li, Bingshi; Cheuk, Kevin Ka Leung; Yang, Di; Lam, Jacky W. Y.; Wan, Li‐Jun; Bai, Chunli; Tang, Ben Zhong

doi:10.1021/ma034275l

Cited by 50 publications

(29 citation statements)

References 20 publications

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“…70,71 There have been several reports of amino acid-based amphiphile materials, such as pH-sensitive amphiphile vesicles applicable to a drug delivery systems 72 and polyacetylene with leucine pendant groups. 73 Amino acid-derived hydrophobic and hydrophilic norbornene monomers 33 and 34 were synthesized and subjected to homo, random and block ROMP (Scheme 22). 74 The hydrophobicity increases with increasing ester monomer content, as confirmed by nuclear magnetic resonance spectroscopic measurements in various solvents and water contact angle measurements of the polymer films.…”

Section: Recent Advances In Rompmentioning

confidence: 99%

Recent advances in ring-opening metathesis polymerization, and application to synthesis of functional materials

Sutthasupa

Shiotsuki

Sanda

2010

Polym J

329

273

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This article reviews the development of catalysts for ring-opening metathesis polymerization (ROMP), synthesis of polymers bearing amino acids and peptides by ROMP of functionalized norbornenes, formation of aggregates and micelles, and applications of the polymers to medical materials. It also describes the control of monomer unit sequences, that is, living polymerization to synthesize block copolymers, and alternating copolymerization that is achieved on the basis of acid-base interactions. Polymer Journal (2010) 42, 905-915; doi:10.1038/pj.2010.94; published online 13 October 2010Keywords: alternating copolymerization; amino acid; block copolymerization; living polymerization; metathesis catalyst; peptide; ROMP INTRODUCTIONOlefin metathesis reactions are metal-mediated carbon-carbon (C-C) double bond exchange processes, 1,2 which were discovered in the mid 1950s. Chauvin proposed the commonly accepted mechanism for metathesis involving a metallacyclobutane, as illustrated in Scheme 1. 3 Initially, olefin metathesis was regarded as an odd reaction, but now it has undoubtedly established the position as one of the most important C-C bond formation reactions applicable to synthesis of a wide variety of useful products. In the early stages, transition metal chlorides were used as catalysts for the reaction, but the transition metal carbene complex catalysts designed by Schrock and Grubbs have remarkably advanced mechanistic analysis and control of catalytic activity by the choice of ligands. In 2005, Chauvin, Grubbs and Schrock were awarded the Nobel Prize in chemistry for development of the metathesis method in organic synthesis.Olefin metathesis polymerization is an application of metathesis reactions to polymer synthesis and includes ring-opening metathesis polymerization (ROMP) and acyclic diene metathesis (ADMET) polycondensation (Scheme 2). ADMET has been extensively developed by Wagener since 1987 4 for the synthesis of polyolefins having regularly spaced functional group branches and high thermal stability and crystallinity. 5,6 ADMET is also useful for synthesizing polymeric materials containing in-chain functionality. Although the general structures of the polymers obtained by ROMP and ADMET are illustratable in the same fashion as shown in Scheme 2, a completely different treatment is necessary from the viewpoint of polymerization kinetics. The former involves chain polymerization, whereas the latter is a step-growth polymerization process.

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Section: Recent Advances In Rompmentioning

confidence: 99%

Recent advances in ring-opening metathesis polymerization, and application to synthesis of functional materials

Sutthasupa

Shiotsuki

Sanda

2010

Polym J

329

273

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“…Because of their characteristic core-shell structure, the polymeric micelles can suppress the protein adsorption on the hydrophilic shell, the immune response and non-specific drug distribution in normal tissues [1]. To date, most studies about polymeric micelles or nanoparticles have been focused on amphiphilic block copolymers, which are highly regular and versatile components for the fabrication of polymeric micelles, while their synthesis often requires nontrivial conditions such as extremely pure reagents, stringently dry environment and rigorously clean reactors [2,3]. Therefore, it is significant to seek more facile protocol for the formation of drug-conjugating polymeric micelles or nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Multidrug nanoparticles based on novel random copolymer containing cytarabine and fluorodeoxyuridine

Yin

et al. 2010

Journal of Colloid and Interface Science

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“…We have concentrated our efforts on the development of OAPAs with naturally occurring building blocks such as amino acids, saccharides, nucleosides, and sterols [62][63][64][65][66][67][68][69][70][71][72][73]. Figure 1.12a shows circular dichroism spectra of a pair of polymers containing d-[22e(d)] and l-α-phenylglycine units [22e(l)].…”

Section: Optical Activitymentioning

confidence: 99%

Synthesis and Functionality of Substituted Polyacetylenes

Liu¹,

Lam²,

Tang³

2010

Design and Synthesis of Conjugated Polymers

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Self-Assembling of an Amphiphilic Polyacetylene Carrying l-Leucine Pendants: A Homopolymer Case

Cited by 50 publications

References 20 publications

Recent advances in ring-opening metathesis polymerization, and application to synthesis of functional materials

Recent advances in ring-opening metathesis polymerization, and application to synthesis of functional materials

Multidrug nanoparticles based on novel random copolymer containing cytarabine and fluorodeoxyuridine

Synthesis and Functionality of Substituted Polyacetylenes

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