Triazolinyl radicals – new additives for controlled radical polymerization

Steenbock, Marco; Klapper, Markus; Müllen, Kläus

doi:10.1002/(sici)1521-3935(19980501)199:5<763::aid-macp763>3.3.co;2-j

Cited by 12 publications

(10 citation statements)

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“…13 The potential of this species to act as mediators in DSSCs is heightened by the known values of redox potentials which lie in the region of interest for the most commonly used dye species 93. In addition, other nitrogen‐based stable radical species such as triazolinyl and benzotriazinyl radicals, which have previously been shown to mediate radical polymerization of styrene may offer the possibility for efficient use in DSSCs 14. 94…”

Section: Common Redox Active Compounds In Dsscs and Crpmentioning

confidence: 99%

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Redox Active Compounds in Controlled Radical Polymerization and Dye‐Sensitized Solar Cells: Mutual Solutions to Disparate Problems

Ballard

Mecerreyes

Asúa

2015

Chemistry A European J

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Controlled radical polymerization (CRP) and dye-sensitized solar cells (DSSCs) are two fields of research that at an initial glance appear to have little in common. However, despite their obvious differences, both in application and in scientific nature, a closer look reveals a striking similarity between many of the compounds widely used as control agents in radical polymerization and as redox couples in dye-sensitized solar cells. Herein, we review the various redox active compounds used and examine the characteristics that give them the ability to perform this dual function. In addition we explore the advances in the understanding of the structural features that enhance their activity in both CRP and DSSCs. It is hoped that such a comparison will be conducive to improving process performance in both fields.

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Section: Common Redox Active Compounds In Dsscs and Crpmentioning

confidence: 99%

“…stable radicals including nitroxide,11 verdazyl,12, 13 triazolinyl,14 cobalt complexes15, 16 dithiocarbamates b[17] and disulfides18…”

Section: Introductionmentioning

confidence: 99%

Redox Active Compounds in Controlled Radical Polymerization and Dye‐Sensitized Solar Cells: Mutual Solutions to Disparate Problems

Ballard

Mecerreyes

Asúa

2015

Chemistry A European J

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“…In particular, in the SFRP process a number of stable radicals have been introduced as the polymerization mediators, e.g. borinate, (arylazo)oxy, triazolinyl, verdazyl and nitroxide . The latter class has been the most extensively studied with efforts focused on the development of new nitroxide radicals that can be effectively used in SFRP under milder reaction conditions for the polymerization of different monomer families …”

Section: Introductionmentioning

confidence: 99%

Benzotriazinyl-mediated controlled radical polymerization of styrene

et al. 2013

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The stable free radical polymerization (SFRP) process based on (1,3-diphenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl), the so-called 'Blatter radical', and several C-7 substituted derivatives is introduced for the first time for the polymerization of styrene. Polystyrenes characterized by polydispersity indices in the 1.05 − 1.27 range were obtained in the presence of the Blatter radical and its derivatives containing CF 3 , Ph, Fur-2-yl and 4-PhC 6 H 4 substituents, while polymerization proceeded either in a non-controlled manner or in very low polymerization yields in the presence of derivatives containing halogen (Cl, Br, I) substituents. This preliminary investigation, demonstrating the potential use of the Blatter radical and its derivatives in mediated SFRP, creates new opportunities to design and develop radicals to optimize performance in such polymerization processes.

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“…4 Unlike living cationic or living anionic polymerization, living free radical polymerization is tolerant to a number of functional groups. 5,6 This characteristic of the polymerization makes it especially attractive for the synthesis of controlled molecular weight polymers to provide better insights into structure-property relationships. For example, side group LC poly(methacrylate)s have been synthesized by GTP 7,8 and living anionic polymerization 9 with varying degrees of success, because of functional group complications.…”

Section: Introductionmentioning

confidence: 99%

“…This technique has been successfully applied to producing macromolecular architectures such as star and graft polymers , …”

Section: Introductionmentioning

confidence: 99%

Highly Reactive 2,5-Disubstituted Styrene-Based Monomer Polymerized via Stable Free Radical Polymerization: Effect of Substitution and Liquid Crystallinity on Polymerization

Gopalan

Ober

2001

Macromolecules

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The stable free radical polymerization (SFRP) of a liquid crystalline monomer 2,5-bis[(4-butylbenzoyl)oxy]styrene, BBOS, was investigated. BBOS is a substituted styrenic monomer, which polymerizes an order of magnitude faster than styrene under identical bulk polymerization conditions. A comparative study of the polymerization behavior in bulk and solution for BBOS and a model compound was undertaken to elucidate the effect of both electron-withdrawing substituents and liquid crystallinity of the monomer on the polymerization kinetics. Molecular simulation was used to identify a non-LC model monomer, 2,5-diacetoxystyrene (DAS). DAS was polymerized by stable free radical polymerization both in bulk and in solution. In all cases narrow molecular weight distribution (<1.4) was obtained. In bulk, DAS polymerized significantly slower than BBOS, whereas in a dilute solution, the rate of polymerization was quite similar. In-situ X-ray studies carried out during polymerization of BBOS in the neat monomer indicate the presence of a nematic phase which could lead to localized ordering of the monomers during polymerization. In comparison, DAS was found to be more reactive than styrene, because of the electronic effect of the acetoxy groups. However, p-acetoxystyrene (PAS) was found to have almost the same observed rate of polymerization as DAS, indicating that steric factors also play an important role in O-substituted compounds.

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Triazolinyl radicals – new additives for controlled radical polymerization

Cited by 12 publications

References 0 publications

Redox Active Compounds in Controlled Radical Polymerization and Dye‐Sensitized Solar Cells: Mutual Solutions to Disparate Problems

Redox Active Compounds in Controlled Radical Polymerization and Dye‐Sensitized Solar Cells: Mutual Solutions to Disparate Problems

Benzotriazinyl-mediated controlled radical polymerization of styrene

Highly Reactive 2,5-Disubstituted Styrene-Based Monomer Polymerized via Stable Free Radical Polymerization: Effect of Substitution and Liquid Crystallinity on Polymerization

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