Novel Trifunctional Building Blocks for Fluorescent Polymers

Batra, Dolly; Shea, Kenneth J.

doi:10.1021/ol035500m

Cited by 12 publications

(5 citation statements)

References 24 publications

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“…For the first reaction step, depending on the desired product, 1 equiv (for MAS) or 2 equiv (for DAS) of pTSI was added to a solution of dry CH 2 Cl 2 and DEGEMA (1 equiv for MAS) or TTEGDMA (1 equiv for DAS). , The reactions were exposed to visible light and monitored via 1 H NMR spectroscopy by looking at the decrease of double bond signal (δ = 6.08 and 5.53 ppm) and the formation of the iodine compound I (δ = 4.47 and 3.90 ppm; d; 2 J = 13.8 Hz). Triethylamine (Et 3 N) was added to deprotonate the iodine compound and consequently cleave off the iodine to yield the kinetic product K. The reaction mixture was refluxed overnight to form the desired thermodynamically stable β-allyl sulfones (AS).…”

Section: Results and Discussionmentioning

confidence: 99%

β-Allyl Sulfones as Addition–Fragmentation Chain Transfer Reagents: A Tool for Adjusting Thermal and Mechanical Properties of Dimethacrylate Networks

et al. 2014

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Dimethacrylates are known to have good photoreactivity, but their radical polymerization usually leads to irregular, highly cross-linked, and brittle polymer networks with broad thermal polymer phase transitions. Here, the synthesis of mono- and difunctional β-allyl sulfones is described, and those substances are introduced as potent addition–fragmentation chain transfer (AFCT) reagents leading to dimethacrylate networks with tunable properties. By controlling the content and functionality of said AFCT reagents, it is possible to achieve more homogeneous networks with a narrow glass transition and an adjustable glass transition temperature (T g), rubber modulus of elasticity (E r), and network density. In contrast to dimethacrylate networks containing monomethacrylates as reactive diluents, the network architecture of the β-allyl sulfone-based dimethacrylate networks is more homogeneous and the tunability of thermal and mechanical properties is much more enhanced. The reactivity and polymerization were investigated using laser flash photolysis, photo-DSC, and NMR, while DMTA and swellability tests were performed to characterize the polymer.

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Section: Results and Discussionmentioning

confidence: 99%

β-Allyl Sulfones as Addition–Fragmentation Chain Transfer Reagents: A Tool for Adjusting Thermal and Mechanical Properties of Dimethacrylate Networks

et al. 2014

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“…In some cases difficulty in cleaving the ester bond by hydrolysis was overcome by reduction with LiAlH 4 , which resulted in conversion of the carboxylic acid groups to alcohols. 488,489 The semi-covalent approach using ester linkages is not only limited to polymeric materials, but was also applied in TiO 2 215 and in the synthesis of 'cored' dendrimers. [490][491][492] In order to avoid crowding in the binding site and to allow unhindered non-covalent rebinding to occur, Whitcombe et al 493,494 introduced the sacrificial spacer approach.…”

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confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Andersson²,

et al. 2006

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Over 1450 references to original papers, reviews and monographs have herein been collected to document the development of molecular imprinting science and technology from the serendipitous discovery of Polyakov in 1931 to recent attempts to implement and understand the principles underlying the technique and its use in a range of application areas. In the presentation of the assembled references, a section presenting reviews and monographs covering the area is followed by papers dealing with fundamental aspects of molecular imprinting and the development of novel polymer formats. Thereafter, literature describing attempts to apply these polymeric materials to a range of application areas is presented.

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“…Synthesis of 2-Propenoic acid, 2.2 0 -[sulfonylbis(methylene)] bis-, diethylester (8) Synthesis is based on procedures given by Batra et al 30 Compound 7 (3.00 g, 11.6 mmol) was dissolved in DMF (100 mL) and to this was added oxone (13.92 g, 45.3 mmol) dissolved in DMF (200 mL). The reaction mixture was stirred under argon at room temperature for 4 h at which point TLC indicated completion.…”

Section: Generalmentioning

confidence: 99%

Allyl sulfides and α‐substituted acrylates as addition–fragmentation chain transfer agents for methacrylate polymer networks

Ligon

Seidler

Gorsche

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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The rapid and uncontrolled nature of network formation from di(meth)acrylate monomers produces high shrinkage stress and results in polymers with oftentimes brittle mechanical properties. Methods for regulating polymerization and network formation are sought. One option is the use of addition–fragmentation chain transfer (AFCT) agents, which are well known to control molecular weight and molecular weight distribution of monofunctional (meth)acrylates. A series of novel and previously described AFCT reagents were synthesized and screened with laser flash photolysis to determine reactivity. Well‐performing AFCT reagents were then tested in polymerizations with monofunctional and difunctional methacrylates. With monofunctional monomers, the molecular weight and polydispersity of the resultant linear polymers tend to decrease with the addition of AFCT agent. In copolymerization with dimethacrylate monomers, the AFCT agents were found to substantially lower and sharpen the glass transition. Sharpness of the glass transition is here indicative of a more regular and homogenous network. After coupling of the instruments, photorheology was performed simultaneously with real‐time IR to show an increase in monomer conversion at the time of gelation, which appears to have a positive effect on reducing shrinkage stress. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 394–406

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Novel Trifunctional Building Blocks for Fluorescent Polymers

Cited by 12 publications

References 24 publications

β-Allyl Sulfones as Addition–Fragmentation Chain Transfer Reagents: A Tool for Adjusting Thermal and Mechanical Properties of Dimethacrylate Networks

β-Allyl Sulfones as Addition–Fragmentation Chain Transfer Reagents: A Tool for Adjusting Thermal and Mechanical Properties of Dimethacrylate Networks

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Allyl sulfides and α‐substituted acrylates as addition–fragmentation chain transfer agents for methacrylate polymer networks

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