Seeing the Light: Advancing Materials Chemistry through Photopolymerization DOI Creative Commons
Nathaniel Corrigan, Jonathan Yeow,

Peter R. Judzewitsch

и другие.

Angewandte Chemie, Год журнала: 2018, Номер 131(16), С. 5224 - 5243

Опубликована: Авг. 1, 2018

Abstract The application of photochemistry to polymer and material science has led the development complex yet efficient systems for polymerization, post‐functionalization, advanced materials production. Using light activate chemical reaction pathways in these not only leads exquisite control over dynamics, but also allows synthetic protocols be easily achieved. Compared polymerization mediated by thermal, chemical, or electrochemical means, photoinduced can potentially offer more versatile methods macromolecular synthesis. We highlight utility as an energy source mediating photopolymerization, present some promising examples which are advancing production through their exploitation photochemistry.

Язык: Английский

A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor–Acceptor Cyanoarenes DOI
Elisabeth Speckmeier, Tillmann G. Fischer, Kirsten Zeitler

и другие.

Journal of the American Chemical Society, Год журнала: 2018, Номер 140(45), С. 15353 - 15365

Опубликована: Окт. 2, 2018

The targeted choice of specific photocatalysts has been shown to play a critical role for the successful realization challenging photoredox catalytic transformations. Herein, we demonstrate implementation rational design strategy series deliberate structural manipulations cyanoarene-based, purely organic donor-acceptor photocatalysts, using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as starting point. Systematic modifications both donor substituents well acceptors' molecular core allowed us identify strongly oxidizing reducing catalysts (e.g., an unprecedented detriflation unactivated naphthol triflate), which additionally offer remarkably balanced redox potentials with predictable trends. Especially halogen arene substitutions are instrumental our alterations catalysts' properties. Based on their preeminent electrochemical and photophysical characteristics, all novel, were evaluated in three challenging, mechanistically distinct classes benchmark reactions (either requiring balanced, highly or properties) enormous potential customizable that outperform complement prevailing typical best photocatalysts.

Язык: Английский

Процитировано

618

Seeing the Light: Advancing Materials Chemistry through Photopolymerization DOI Creative Commons
Nathaniel Corrigan, Jonathan Yeow,

Peter R. Judzewitsch

и другие.

Angewandte Chemie International Edition, Год журнала: 2018, Номер 58(16), С. 5170 - 5189

Опубликована: Авг. 1, 2018

The application of photochemistry to polymer and material science has led the development complex yet efficient systems for polymerization, post-functionalization, advanced materials production. Using light activate chemical reaction pathways in these not only leads exquisite control over dynamics, but also allows synthetic protocols be easily achieved. Compared polymerization mediated by thermal, chemical, or electrochemical means, photoinduced can potentially offer more versatile methods macromolecular synthesis. We highlight utility as an energy source mediating photopolymerization, present some promising examples which are advancing production through their exploitation photochemistry.

Язык: Английский

Процитировано

535

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis DOI
Nicholas E. S. Tay, Dan Lehnherr, Tomislav Rovis

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2487 - 2649

Опубликована: Ноя. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Язык: Английский

Процитировано

361

Atom Transfer Radical Polymerization: Billion Times More Active Catalysts and New Initiation Systems DOI
Thomas G. Ribelli, Francesca Lorandi, Marco Fantin

и другие.

Macromolecular Rapid Communications, Год журнала: 2018, Номер 40(1)

Опубликована: Окт. 30, 2018

Approaching 25 years since its invention, atom transfer radical polymerization (ATRP) is established as a powerful technique to prepare precisely defined polymeric materials. This perspective focuses on the relation between structure and activity of ATRP catalysts, consequent choice initiating system, which are paramount aspects well-controlled polymerizations. The mechanism discussed, including effect kinetic thermodynamic parameters side reactions affecting catalyst. coordination chemistry copper complexes used in reviewed chronological order, while emphasizing structure-activity correlation. ATRP-initiating systems described, from normal low ppm Cu systems. Most recent advancements regarding dispersed media oxygen-tolerant techniques presented, well future opportunities that arise progressively more active catalysts deeper mechanistic understanding.

Язык: Английский

Процитировано

256

Highly Conjugated Three-Dimensional Covalent Organic Frameworks Based on Spirobifluorene for Perovskite Solar Cell Enhancement DOI
Chenyu Wu, Yamei Liu, Hui Liu

и другие.

Journal of the American Chemical Society, Год журнала: 2018, Номер 140(31), С. 10016 - 10024

Опубликована: Июль 14, 2018

Highly conjugated three-dimensional covalent organic frameworks (3D COFs) were constructed based on spirobifluorene cores linked via imine bonds (SP-3D-COFs) with novel interlacing conjugation systems. The crystalline structures confirmed by powder X-ray diffraction and detailed structural simulation. A 6- or 7-fold interpenetration was formed depending the structure of linking units. obtained SP-3D-COFs showed permanent porosity high thermal stability. In application for solar cells, simple bulk doping to perovskite cells (PSCs) substantially improved average power conversion efficiency 15.9% SP-3D-COF 1 18.0% 2 as compared reference undoped PSC, while offering excellent leakage prevention in meantime. By aid both experimental computational studies, a possible photoresponsive perovskite–SP-3D-COFs interaction mechanism proposed explain improvement PSC performance after doping.

Язык: Английский

Процитировано

244

Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis DOI Creative Commons
Daniel A. Corbin, Garret M. Miyake

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 1830 - 1874

Опубликована: Ноя. 29, 2021

The development of photoinduced organocatalyzed atom transfer radical polymerization (O-ATRP) has received considerable attention since its introduction in 2014. Expanding on many the advantages traditional ATRP, O-ATRP allows well-defined polymers to be produced under mild reaction conditions using organic photoredox catalysts. As a result, opened access range sensitive applications where use metal catalyst could concern, such as electronics, certain biological applications, and coordinating monomers. However, key limitations this method remain necessitate further investigation continue field. such, review details achievements made to-date well future research directions that will expand capabilities application landscape O-ATRP.

Язык: Английский

Процитировано

233

A Rational Approach to Organo‐Photocatalysis: Novel Designs and Structure‐Property Relationships DOI
Alberto Vega‐Peñaloza, Javier Mateos, Xavier Companyó

и другие.

Angewandte Chemie International Edition, Год журнала: 2020, Номер 60(3), С. 1082 - 1097

Опубликована: Июнь 22, 2020

Organic photocatalysts are emerging as viable and more sustainable tools than metal complexes. Recently, the field of organo-photocatalysis has experienced an explosion in terms applications, redesign well-established systems, identification novel scaffolds. A rational approach to structural modification different is key accessing unprecedented reactivity, while improving their catalytic performances. We herein discuss concepts underpinning scaffold some most recently used analyze how specific changes alter physicochemical redox properties.

Язык: Английский

Процитировано

213

PET-RAFT polymerisation: towards green and precision polymer manufacturing DOI

Jamie Phommalysack-Lovan,

Yingying Chu, Cyrille Boyer

и другие.

Chemical Communications, Год журнала: 2018, Номер 54(50), С. 6591 - 6606

Опубликована: Янв. 1, 2018

The necessity of sustainable development in the chemical industry has continuously drawn attention to find safe, environmentally friendly and atom-economic processes, which is defined 12 principles green chemistry. Merging photoredox catalysis reversible addition-fragmentation chain transfer (RAFT) polymerisation, photoinduced electron/energy (PET)-RAFT process opened up a new way performing deactivation radical polymerisation for well-defined polymer synthesis using light as an external stimulus. While providing increased level control (spatiotemporal, wavelength, intensity control) over PET-RAFT many attractive attributes (abundant catalyst availability, recyclability, selectivity oxygen tolerance) be sustainable, intriguing precision manufacturing industry.

Язык: Английский

Процитировано

208

Recent progress in the development of transition-metal based photoredox catalysts DOI
Felix Glaser, Oliver S. Wenger

Coordination Chemistry Reviews, Год журнала: 2019, Номер 405, С. 213129 - 213129

Опубликована: Дек. 10, 2019

Язык: Английский

Процитировано

204

Evolution and Future Directions of Metal-Free Atom Transfer Radical Polymerization DOI Creative Commons
Emre H. Discekici, Athina Anastasaki, Javier Read de Alaniz

и другие.

Macromolecules, Год журнала: 2018, Номер 51(19), С. 7421 - 7434

Опубликована: Сен. 25, 2018

The increasing impact of atom transfer radical polymerization (ATRP) in fields beyond traditional polymer science has necessitated the development alternative strategies for controlling growth. Driven by applications that are sensitive to metal ion contamination, "greener" methodologies emerging as a powerful conventional ATRP. Organic catalysis represents major evolution ATRP with metal-free systems holding significant potential user-friendly methods utility biological and microelectronic applications. In addition, shifting from combination thermal activation/metal ions/ligands simpler organic catalysis/light activation increases compatibility functional monomers allows novel surface patterning strategies. Herein, we highlight key discoveries recent developments ATRP, while providing perspective future opportunities this area.

Язык: Английский

Процитировано

200