4.4 Article

LED-Induced Polymerization (385, 405, and 455 nm) Using Star-Shaped Tris(4-(thiophen-2-yl)phenyl)amine Derivatives as Light-Harvesting Photoinitiators

期刊

MACROMOLECULAR CHEMISTRY AND PHYSICS
卷 216, 期 2, 页码 218-227

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/macp.201400403

关键词

cationic photopolymerization; photoinitiators; radical photopolymerization; triphenylamine dyes; UV or visible LEDs

资金

  1. Universitaire de France

向作者/读者索取更多资源

Two star-shaped tris(4-(thiophen-2-yl)phenyl)amine derivatives, namely tris(4-(5-(3-pentylthieno[3,2-b]thiophen-5-yl)thiophen-2-yl)phenyl) amine and tris(4-(5-(3-pentyl-2-(thiophen-2-yl)thieno[3,2-b]thiophen-5-yl) thiophen-2-yl) phenyl) amine, are developed as photoinitiators for radical and cationic polymerizations under near-UV and visible light-emitting diodes (LEDs) (e.g., 385, 405, and 455 nm). When used in combination with an iodonium salt (and optionally N-vinyl carbazole) or an amine/alkyl halide couples, they lead to excellent photoinitiating abilities for the polymerization of epoxides or (meth) acrylates under air. Compared with commercial photoinitiators, i.e., camphorquinone-based systems or bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide, the novel photoinitiators exhibit noticeably higher polymerization efficiencies under air (epoxide conversions = 41-57% vs approximate to 0%, halogen lamp exposure; methacrylate conversions = 50-55% vs 44%, LED at 405 nm exposure; methacrylate conversions = 34-42% vs 0-8%, LED at 455 nm exposure). These systems are also interesting in overcoming oxygen inhibition. The photochemical mechanisms are studied by steady-state photolysis, electron spin resonance spin trapping, fluorescence, cyclic voltammetry, and laser flash photolysis techniques.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.4
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Chemistry, Multidisciplinary

Morphology and Viscosity Changes after Reactive Uptake of Isoprene Epoxydiols in Submicrometer Phase Separated Particles with Secondary Organic Aerosol Formed from Different Volatile Organic Compounds

Ziying Lei, Nicole E. Olson, Yue Zhang, Yuzhi Chen, Andrew T. Lambe, Jing Zhang, Natalie J. White, Joanna M. Atkin, Mark M. Banaszak Holl, Zhenfa Zhang, Avram Gold, Jason D. Surratt, Andrew P. Ault

Summary: The reactive uptake of VOC-derived semivolatile oxidation products on inorganic-organic submicron particles was studied, and it was found that the viscosity and morphology of the particles changed significantly after the uptake. The changes were highly dependent on the VOC precursor, and the impact on air quality and climate predictions could be altered.

ACS EARTH AND SPACE CHEMISTRY (2022)

Article Polymer Science

Recent advances on photobleachable visible light photoinitiators of polymerization

Frederic Dumur

Summary: Photopolymerization under visible light has made significant progress in recent years, thanks to the development of new irradiation setups based on LEDs. Efficient photoinitiating systems that match the light sources used in 3D printers have become increasingly important. However, visible light photoinitiators, although they increase the thickness of the polymerized films, are often strongly colored compounds that hinder the use of photopolymers for everyday applications. To tackle this issue, the development of photobleachable photoinitiating systems has emerged as a promising research field. This review provides an overview of recent advances in photobleachable photoinitiators and discusses the exploration of various structures to address the challenge of achieving colorless coatings.

EUROPEAN POLYMER JOURNAL (2023)

Article Biochemistry & Molecular Biology

Synthesis and Optical Properties of a Series of Push-Pull Dyes Based on Pyrene as the Electron Donor

Thanh-Tuan Bui, Sebastien Peralta, Frederic Dumur

Summary: Fifteen push-pull dyes based on tetracyclic polyaromatic pyrene were synthesized and their optical properties were investigated in twenty-two solvents with different polarities. Surprisingly, contrary to conventional D-pi-A push-pull dyes, negative solvatochromism was observed in many of the dyes. Photoluminescence and thermal properties were also examined, and theoretical calculations were conducted to support the experimental findings.

MOLECULES (2023)

Review Polymer Science

Recent advances on Anthraquinone-based photoinitiators of polymerization

Frederic Dumur

Summary: Anthraquinone has been identified as a promising scaffold for designing photoinitiating systems activable in the visible range and under low light intensity. Molecular engineering has allowed the development of water-soluble, panchromatic, or photobleachable dyes based on this scaffold. This review provides an overview of recent advances in photopolymerization using anthraquinone-based photoinitiating systems.

EUROPEAN POLYMER JOURNAL (2023)

Article Polymer Science

Synergistic approach of type I hybrid complexes for highly efficient metal-based initiating strategies: Toward low energy-consuming polymerization for thermoplastic composite implementation

Marie Le Dot, Nicolas Giacoletto, Fabrice Morlet-Savary, Bernadette Graff, Valerie Monnier, Didier Gigmes, Malek Nechab, Frederic Dumur, Pierre Gerard, Jacques Lalevee

Summary: A new configuration of Metal Acetylacetonate Bidentate Ligand Interaction (MABLI) mechanism has been discovered for initiating the polymerization of recyclable Elium (R) thermoplastic resins under mild conditions. The presence of a phosphine oxide significantly reduces curing time and achieves nearly 100% conversion. Additionally, the combination of MABLI and photoactivation in a dual cure approach enhances the polymerization efficiency.

EUROPEAN POLYMER JOURNAL (2023)

Review Polymer Science

Recent advances on photoinitiating systems designed for solar photocrosslinking polymerization reactions

Frederic Dumur

Summary: Photopolymerization is a research field that aims to replace energy-consuming UV irradiation setups with energy-saving light-emitting diodes (LEDs) or even sunlight as a light source. Various dyes have been developed to efficiently promote polymerization processes under sunlight, enabling the use of photopolymerization in outdoor applications. This review provides an overview of different photoinitiating systems developed for polymerization processes under sunlight or daylight, comparing their efficiency to that of artificial light sources.

EUROPEAN POLYMER JOURNAL (2023)

Review Chemistry, Physical

Recent Advances on Furan-Based Visible Light Photoinitiators of Polymerization

Frederic Dumur

Summary: Photopolymerization is an active research field focused on polymerizing in greener conditions using visible light instead of traditional UV light. Furane is an interesting candidate for designing photocatalysts of polymerization due to its low cost and easy chemical modification. This review provides an overview of furane-based photoinitiator design and compares them to reference systems to demonstrate their potential in innovative structures.

CATALYSTS (2023)

Review Chemistry, Physical

Recent Advances on Quinoxaline-Based Photoinitiators of Polymerization

Frederic Dumur

Summary: Photopolymerization uses light as the activation source to convert liquid monomers to polymers. The development of visible light photo-initiating systems and the search for new dyes that can polymerize a resin within seconds are ongoing. Quinoxaline has been identified as a promising scaffold for designing UV-centered and visible light photo-initiating systems. This review provides an overview of different quinoxaline-based dyes and compares them with reference systems to demonstrate their significance.

CATALYSTS (2023)

Article Polymer Science

Recent advances on naphthoquinone-based photoinitiators of polymerization

Frederic Dumur

Summary: Photoinitiating systems activable under visible light are the subject of many studies due to their ability to achieve higher light penetration. The reactivity of these systems can be improved by investigating new dye structures, including naphthoquinones which have been underexplored as visible light photoinitiators of polymerization. Recent developments have shown promising results in designing photoinitiators with naphthoquinone, paving the way for future advancements. This review provides an overview of different photoinitiators containing a naphthoquinone unit and compares their polymerization efficiencies with reference compounds.

EUROPEAN POLYMER JOURNAL (2023)

Review Polymer Science

Recent advances on diaryliodonium-based monocomponent photoinitiating systems

Frederic Dumur

Summary: Iodonium salts, a type of cationic photoinitiators, have a long history of use in the polymerization of epoxides or vinyl ethers. However, their UV-centered absorption restricts their use to the visible range through a photosensitization process. To simplify the composition of photopolymerizable resins, various dyes have been covalently linked to iodonium salts, resulting in monocomponent photoinitiating systems. This review provides an overview of the different dyes connected to iodonium salts.

EUROPEAN POLYMER JOURNAL (2023)

Article Polymer Science

Recent advances on visible light bodipys and related difluoroborane structures-based photoinitiating systems

Frederic Dumur

Summary: Photopolymerization is undergoing a revolution with the emergence of affordable and easily accessible LEDs, making polymerization possible under safe and energy-saving conditions. Bodipys, which are renowned for their high photoluminescence quantum yields, exceptional molar extinction coefficients, and narrow absorption and emission bands, have been identified as a promising platform for designing photoinitiators. Recent advancements in difluoroborane derivatives, such as boranils, squaraine-derived structures, and 2-phenacylbenzoxazole difluoroboranes, have expanded the application scope of photopolymerization. This review presents the various bodipys, boranils, squaraine-based difluoroborate complexes, and 2-phenacylbenzoxazole difluoroboranes used in developing photoinitiating systems and compares their efficiency to reference photoinitiating systems.

EUROPEAN POLYMER JOURNAL (2023)

Review Polymer Science

Recent Advances in Monocomponent Visible Light Photoinitiating Systems Based on Sulfonium Salts

Frederic Dumur

Summary: In recent years, research efforts have focused on multicomponent photoinitiating systems, especially for the design of visible light photoinitiating systems. Monocomponent Type II photoinitiators have been designed to simplify the elaboration of photocurable resins. Sulfonium salts, as remarkable photoinitiators, lack absorption in the visible range, leading to various structural modifications for redshifting their absorptions. This work provides an overview of different sulfonium salts activable under visible light.

POLYMERS (2023)

Article Chemistry, Multidisciplinary

Carbazole-fused coumarin based oxime esters (OXEs): efficient photoinitiators for sunlight driven free radical photopolymerization

Yijun Zhang, Zheng Liu, Timur Borjigin, Bernadette Graff, Fabrice Morlet-Savary, Michael Schmitt, Didier Gigmes, Frederic Dumur, Jacques Lalevee

Summary: Seventeen carbazole-fused coumarin-based oxime esters were developed as efficient and visible light-absorbing initiators for polymerization. Certain oxime esters exhibited comparable or better photoinitiation performance than the benchmark photoinitiator under LED irradiation. These oxime esters also showed thermal initiation behavior and could be used as both thermal and photo-initiators. Moreover, two oxime esters, OXE-1 and OXE-5, were found to be sunlight activable and achieved high monomer conversion rates within one hour.

GREEN CHEMISTRY (2023)

Article Chemistry, Physical

Self-assembly of s-indacene-tetrone on Cu(111): molecular trapping and patterning of Cu adatoms

Nataliya Kalashnyk, Adam Hassan Denawi, Frederic Dumur, Didier Gigmes, Xavier Bouju, Sylvain Clair

Summary: The supramolecular self-assembly of s-indacene-1,3,5,7(2H,6H)-tetrone on the Cu(111) surface was investigated and six different phases were found, driven by different interactions. Host-guest interactions allowed for the accommodation of molecular or metal clusters inside the nanoporous patterns. Three metal-organic networks led to the creation of regular arrays of isolated metal adatoms or adatom clusters.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2023)

暂无数据