Repairable photoactive polymer systems via metal–terpyridine-based self-assembly

Jeong, Dong−Cheol; Lee, Jookyeong; Ro, Yu Hyeon; Song, Changsik

doi:10.1039/c7py00095b

Cited by 12 publications

(17 citation statements)

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“…The authors tested the HPCat for the singlet oxygen production using α-terpinene (44) as a singlet oxygen trap (discussed in the next section), which proved successful. However, we would argue that this is not conclusive evidence that the mechanism occurs via singlet oxygen and not photoredox, as other reports tend to favour the photoredox mechanism for TiO 2 and transition metal-based photocatalysts [250][251][252][253]. Additionally, photoredox and photosensitisation ability are not mutually exclusive, so the positive result for singlet oxygen production does Scheme 16: Scheme of the oxidative coupling of benzylamines with the HOTT-HATN HPCat and selected examples of the benzyl benzaldimine products 39a-f.…”

Section: The Reaction Was Previously Reported Using a [Ru(bpy) 3 ]Clmentioning

confidence: 61%

Heterogeneous photocatalysis in flow chemical reactors

Thomson

Lee

Vilela

2020

Beilstein J. Org. Chem.

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The synergy between photocatalysis and continuous flow chemical reactors has shifted the paradigms of photochemistry, opening new avenues of research with safer and scalable processes that can be readily implemented in academia and industry. Current state-of-the-art photocatalysts are homogeneous transition metal complexes that have favourable photophysical properties, wide electrochemical redox potentials, and photostability. However, these photocatalysts present serious drawbacks, such as toxicity, limited availability, and the overall cost of rare transition metal elements. This reduces their long-term viability, especially at an industrial scale. Heterogeneous photocatalysts (HPCats) are an attractive alternative, as the requirement for the separation and purification is largely removed, but typically at the cost of efficiency. Flow chemical reactors can, to a large extent, mitigate the loss in efficiency through reactor designs that enhance mass transport and irradiation. Herein, we review some important developments of heterogeneous photocatalytic materials and their application in flow reactors for sustainable organic synthesis. Further, the application of continuous flow heterogeneous photocatalysis in environmental remediation is briefly discussed to present some interesting reactor designs that could be implemented to enhance organic synthesis.

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Section: The Reaction Was Previously Reported Using a [Ru(bpy) 3 ]Clmentioning

confidence: 61%

Heterogeneous photocatalysis in flow chemical reactors

Thomson

Lee

Vilela

2020

Beilstein J. Org. Chem.

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“…A synthesis was conducted according to the procedure described in Reference [13]. Cis-5-norbornene- exo -2,3-dicarboxylic anhydride (0.50 g, 3.0 mmol), 3-aminopropionic acid (0.34 g, 3.8 mmol), and triethylamine (0.039 g, 0.38 mmol) were mixed in 10 mL toluene, in a 25 mL round-bottom flask, fitted using a Dean–Stark apparatus.…”

Section: Methodsmentioning

confidence: 99%

“…To prepare functionalized polymers, several methods have been established, such as the ionic and free radical polymerization of vinyl monomers, group transfer polymerization (GTP), and more recently, ring-opening metathesis polymerization (ROMP) [12]. Among these methods, ROMP is an attractive method because it is robust, produces an absolutely linear material, and is amenable to the formation of various copolymers of a controlled architecture [13,14]. Polymers produced using ROMP can have a variety of chelating groups including terpyridine moieties, which can act as an anchor group in the binding of metal complexes with a polymer chain [14].…”

Section: Introductionmentioning

confidence: 99%

“…A member of our group recently synthesized a terpyridine-based norbornene polymer using ROMP, and conducted visible-light induced photocatalytic oxidation of benzylamine into imine, to confirm its applicability as a regenerative and repairable photocatalyst. The metallo photo-active complex polymer, which can bind to a ruthenium(II) complex (Ru(bpy) 2 (bpy–tpy)Cl 2 ) through metal ions, was applied to a reversible photo-catalyst [13]. Other researchers have reported a chemodosimeter for chemical warfare agents (CWAs), using norbornene-derived terpyridine materials [15].…”

Section: Introductionmentioning

confidence: 99%

“…Other researchers have reported a chemodosimeter for chemical warfare agents (CWAs), using norbornene-derived terpyridine materials [15]. Although terpyridine-based norbornene polymers have been reported in the application of photocatalysts [13], chemo-sensors [15], and anion exchange membranes [16], they have yet to be reported in studies on self-healing.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Reversible Assembly of Terpyridine Incorporated Norbornene-Based Polymer via a Ring-Opening Metathesis Polymerization and Its Self-Healing Property

Lee¹,

Moon²,

Paeng³

et al. 2018

Polymers

Self Cite

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We induced a terpyridine moiety into a norbornene-based polymer to demonstrate its self-healing property, without an external stimulus, such as light, heat, or healing agent, using metal–ligand interactions. We synthesized terpyridine incorporated norbornene-based polymers using a ring-opening metathesis polymerization. The sol state of diluted polymer solutions was converted into supramolecular assembled gels, through the addition of transition metal ions (Ni2+, Co2+, Fe2+, and Zn2+). In particular, a supramolecular complex gel with Zn2+, which is a metal with a lower binding affinity, demonstrated fast self-healing properties, without any additional external stimuli, and its mechanical properties were completely recovered.

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Metal‐Terpyridine Assembled Functional Materials for Electrochromic, Catalytic and Environmental Applications

Jena

Mandal

Choudhury

2022

The Chemical Record

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Molecular assembly induced by metal-terpyridine-based coordinative interactions has become an emergent research topic due to its ease of synthesis and diverse applications. This article highlights recent significant developments in the metal-terpyridine-based supramolecular architectures. At first, the design aspect of the molecular building blocks has been described, followed by elaboration on how the ligand backbone plays an important role for achieving different dimensionalities of the resulting assemblies which exhibit a wide range of potential applications. After that, we discussed different synthetic approaches for constructing these assemblies, and finally, we focused on their significant developments in three specific areas, viz., electrochromic materials, catalysis and a new application in wastewater treatment. In the field of electrochromic materials, these assemblies made important advancements in various aspects like sub-second switching time (< 1 s), low switching voltage (< 1 V), increased switching stability (> 10000 cycles), tuning of multiple colors by using multimetallic systems, fabrication of charge storing electrochromic devices, utilizing and storing solar energy etc. Similarly, the catalysis field witnessed application of the metal-terpyridine assemblies in CÀ H monohalogenation, heterogeneous Suzuki-Miyaura coupling, photocatalysis, reduction of carbon dioxide, etc. Finally, the environmental application of these coordination assemblies includes capturing Cr(VI) from waste water efficiently with high capture capacity, good recyclability, wide pH independency etc.

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Repairable photoactive polymer systems via metal–terpyridine-based self-assembly

Abstract: The photocatalytic activity of polymeric systems ceased upon disassembly and was restored upon assembly through metal ion–ligand interaction.

Cited by 12 publications

References 50 publications

Heterogeneous photocatalysis in flow chemical reactors

Heterogeneous photocatalysis in flow chemical reactors

Reversible Assembly of Terpyridine Incorporated Norbornene-Based Polymer via a Ring-Opening Metathesis Polymerization and Its Self-Healing Property

Metal‐Terpyridine Assembled Functional Materials for Electrochromic, Catalytic and Environmental Applications

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