Supramolecular association of acid terminated polydimethylsiloxanes

Abed, S.; Boileau, Sylvie; Bouteiller, Laurent; Lacoudre, Nelly

doi:10.1007/s002890050154

Cited by 16 publications

(10 citation statements)

References 31 publications

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“…62 Only a slight change in material properties was observed when poly(dimethylsiloxanes) (PDMS) were functionalised with benzoic acid groups. 63 Nucleobases were used as recognition motifs to functionalize low molecular weight prepolymers by the groups of Rowan 64,65 and Long. [66][67][68] Upon modification of the bisamino end-groups of telechelic PTHF with a molecular weight around 2 kg mol À1 with adenine-or cytosine-derivatives, respectively polymers 1 and 2, the material properties changed dramatically from a soft waxy solid to flexible materials with enough mechanical stability to be processed into fibers and films (Fig.…”

Section: The Biomaterialsmentioning

confidence: 99%

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Dankers

Meijer²

2007

Bulletin of the Chemical Society of Japan

123

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Supramolecular chemistry is an exciting area of science that plays a central role in bringing different disciplines together, ranging from molecular medicine to nanotechnology. Materials science based on supramolecular interactions is an emerging field, which has made important steps forward in the past ten years. The self-assembly of small synthetic molecules into long-chain architectures gives rise to the careful design of supramolecular polymers or fibers based on highly directional, reversible, non-covalent interactions. Much afford is put into the development of supramolecular (polymeric) materials with true materials properties, both in solution and in the solid state. These supramolecular materials are beginning to reach the market in all kind of applications. The field of regenerative medicine in general and that of tissue engineering in particular is one of the most challenging areas in which supramolecular materials might have a high potential. In tissue engineering, the biological environment and the interactions of cells with the artificial biomaterial is of utmost importance for the functioning of the implant, i.e. the engineered tissue. Ideal biomaterials do not only have to fulfil the biomaterials trinity of tuneable mechanical properties, regulation of the degradability and the ease for bioactivity incorporation, but also have to mimic the natural environment where the materials are brought into. Therefore, a modular, self-assembly approach using several supramolecular building blocks is an exquisite way to produce such ''responsive'' biomaterials. It is proposed that the artificial materials described in this account have the same type of dynamic ability to adapt its biofunctionality as is so well known for the living cells in the host tissue. This account will highlight two systems, i.e. self-assembling oligopeptide fibers as pioneered by Stupp et al. and Zhang et al., and our hydrogen-bonded supramolecular polymers, to show the potential of a modular approach to dynamic biomaterials for tissue engineering.

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Section: The Biomaterialsmentioning

confidence: 99%

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Dankers

Meijer²

2007

Bulletin of the Chemical Society of Japan

123

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“…Synthesis . Synthesis of 1 and 2 has been reported previously . Monofunctional oligomer 3 was synthesized analogously (Figure ): 5.00 g (16 × 10 -3 equiv of SiH) of α,ω-hydride-terminated PDMS (Hüls America Inc., n = 8, I p = 1.1), 1.06 g (4 × 10 -3 mol) of p -allyloxybenzylbenzoate, 1.20 g (12 × 10 -3 mol) of vinyltrimethylsilane (Aldrich), and 5 mL of toluene (distilled over sodium) were introduced in a round-bottom flask.…”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of 1 and 2 has been reported previously . Monofunctional oligomer 3 was synthesized analogously (Figure ): 5.00 g (16 × 10 -3 equiv of SiH) of α,ω-hydride-terminated PDMS (Hüls America Inc., n = 8, I p = 1.1), 1.06 g (4 × 10 -3 mol) of p -allyloxybenzylbenzoate, 1.20 g (12 × 10 -3 mol) of vinyltrimethylsilane (Aldrich), and 5 mL of toluene (distilled over sodium) were introduced in a round-bottom flask. After purging with nitrogen, 9 μL of platinum catalyst PC085 (platinum−cyclovinylmethylsiloxane complex from Hüls America Inc.) ([Pt]/[SiH] = 10 -4 ) was added, and the reaction mixture was heated at 65 °C for 4 days.…”

Section: Methodsmentioning

confidence: 99%

“…However, characterizing in detail the dependence of molecular weight of hydrogen-bonded supramolecular polymers on concentration, solvent polarity, and temperature is important for the development of potential applications. With this aim in mind, we have designed and synthesized , a model system: benzoic acid-terminated poly(dimethylsiloxane)s 1 (Figure ), which are highly soluble in nonpolar solvents due to the siloxane backbone and in which the benzoic acid moieties form reasonably strong hydrogen-bonded dimers. Poly(dimethylsiloxane)s 2 and 3 (Figure ) were also synthesized and used as references because they contain 0 or 1 benzoic acid group, respectively.…”

Section: Introductionmentioning

confidence: 99%

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Supramolecular Association of Acid-Terminated Poly(dimethylsiloxane)s. 2. Molecular Weight Distributions

2000

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Association through hydrogen bonding of benzoic acid-terminated poly(dimethylsiloxane) 1 in low-polarity solvents has been studied by FTIR spectroscopy and viscosimetry. At high concentrations, chain extension leads to high viscosity values, whereas at low concentrations, intramolecular hydrogen bonding is responsible for the formation of low-viscosity cyclic species. A quantitative model based on Jacobson-Stockmayer theory and describing the competition between chain extension and macrocyclization is presented. On the basis of this model, the molecular weight distributions of ring and chain fractions has been calculated as a function of concentration in three different solvents. The length of the siloxane backbone has been shown to have a large influence on the cyclic weight fraction and on the average molecular weight.

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“…The molecular recognition‐directed association between monomers bearing complementary hydrogen bonding groups leads to linear supramolecular polymers 1–38. The formation of such reversible polymers from monomers linked through sextuple hydrogen‐bonding arrays has been recently reported 17, 38.…”

Section: Introductionmentioning

confidence: 99%

Fibrillar structure of self‐assemblies formed from heterocomplementary monomers linked through sextuple hydrogen‐bonding arrays

Buhler

Candau

Schmidt

et al. 2006

J Polym Sci B Polym Phys

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The nanostructure of the fibrillar supramolecular aggregates generated in decane solutions of homoditopic heterocomplementary monomers forming sextuple hydrogen-bond-mediated self-assemblies was investigated by small-angle neutron scattering and cryogenic-temperature transmission electron microscopy. The persistence length (L p ) of the fibrillar aggregates was found to be $18 nm, as inferred from combined measurements of the radius of gyration and of the contour length. The values of both the weight-average molecular weight and the mass per unit length of the fibers suggest that the latter consist of few aggregated monomolecular wires. At T ¼ 25 8C, the formation of branched aggregates occurs around the crossover concentration, C*, between the dilute and semidilute regimes, whereas the classical behavior of equilibrium polymers is observed at T ¼ 65 8C.

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Supramolecular association of acid terminated polydimethylsiloxanes

Cited by 16 publications

References 31 publications

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Supramolecular Association of Acid-Terminated Poly(dimethylsiloxane)s. 2. Molecular Weight Distributions

Fibrillar structure of self‐assemblies formed from heterocomplementary monomers linked through sextuple hydrogen‐bonding arrays

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