Chlorophyll derivatives as catalysts and comonomers for atom transfer radical polymerizations

Gajewska, Bernadetta; Raccio, Samuel; Rodriguez, Kyle J.; Bruns, Nico

doi:10.1039/c8py01492b

Cited by 16 publications

(15 citation statements)

References 78 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our group has recently applied the cofactor copper Ce6 as a catalyst in atom transfer radical polymerisations (ATRP). [21] Compared to the native protoporphyrin IX (PPIX), Ce6 contains an unsaturated pyrrole ring and an extra carboxylic group (see Scheme S1 for the structures). Ce6 might create a more electron-deficient environment to the metal centre and form a stronger oxidising compound II for oxidation reactions when reconstituted in Mb.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, except for iron chlorin e6 myoglobin (FeCe6‐Mb), [19e] other Ce6‐containing Mb variants have not been reported. Our group has recently applied the cofactor copper Ce6 as a catalyst in atom transfer radical polymerisations (ATRP) [21] . Compared to the native protoporphyrin IX (PPIX), Ce6 contains an unsaturated pyrrole ring and an extra carboxylic group (see Scheme S1 for the structures).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Peroxidase Activity of Myoglobin Variants Reconstituted with Artificial Cofactors

et al. 2022

Self Cite

View full text Add to dashboard Cite

Myoglobin (Mb) can react with hydrogen peroxide (H 2 O 2 ) to form a highly active intermediate compound and catalyse oxidation reactions. To enhance this activity, known as pseudoperoxidase activity, previous studies have focused on the modification of key amino acid residues of Mb or the heme cofactor. In this work, the Mb scaffold (apo-Mb) was systematically reconstituted with a set of cofactors based on six metal ions and two ligands. These Mb variants were fully characterised by UV-Vis spectroscopy, circular dichroism (CD) spectroscopy, inductively coupled plasma mass spectrometry (ICP-MS) and native mass spectrometry (nMS). The steady-state kinetics of guaiacol oxidation and 2,4,6-trichlorophenol (TCP) dehalogenation catalysed by Mb variants were determined. Mb variants with iron chlorin e6 (FeÀ Ce6) and manganese chlorin e6 (MnÀ Ce6) cofactors were found to have improved catalytic efficiency for both guaiacol and TCP substrates in comparison with wild-type Mb, i. e. Fe-protoporphyrin IX-Mb. Furthermore, the selected cofactors were incorporated into the scaffold of a Mb mutant, swMb H64D. Enhanced peroxidase activity for both substrates were found via the reconstitution of FeÀ Ce6 into the mutant scaffold.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Peroxidase Activity of Myoglobin Variants Reconstituted with Artificial Cofactors

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…It has been proven that the polymerization takes place in the C3-position of the chlorin macrocycle. 35,36 Although the reactivity of the vinyl group on a Chl derivative is mentioned to be too low to form homopolymers in radical polymerizations, 37 we successfully performed electropolymerization to get the thin film materials derived from MChl monomers. The formation of a polymerized structure was confirmed by ultraviolet−visible (UV−Vis) absorption spectral changes as well as scanning electron microscopy (SEM) observations.…”

Section: ■ Introductionmentioning

confidence: 99%

Biopolymer Films of Metal-Coordinated Chlorophyll-a Derivatives for “Green” Supercapacitor Electrodes

Zhang

Ren

Liu

et al. 2022

ACS Appl. Energy Mater.

View full text Add to dashboard Cite

Chlorophylls (Chls) are the most naturally abundant organic dye pigments on earth. However, there is little research on Chl polymers so far. In this paper, we demonstrate the fabrication of a series of polymerized chlorophyll-a derivatives with different central metals (PolyMChls, M = Mg, Co, Ni, Cu, Zn, and Ga) via the electrochemical coupling of a peripheral vinyl group at the C3-position on the chlorin macrocycle. The formation of PolyMChls is confirmed by the broadening and slight red-shift of the Soret band in their ultraviolet–visible absorption spectra. PolyMChl films yield a morphology of uniform stacked nanospheres (PolyCuChl ∼ 237 nm), while the original MChl particles are irregular with a size of about 10 μm by scanning electron microscopy. When these PolyMChl films are employed as the working electrodes in a three-electrode system, the highest capacitance of 334 F g–1 at 5 mV s–1 is obtained for PolyCuChl. Basing on the widely existing Chl derivatives, we find a new biopolymer family. The great potential of biopolymer PolyMChl is also exhibited in the energy storage area.

show abstract

“…For the technical imitation of photosynthesis, however, copper 3 or zinc 4 are used as central atoms, since isolated chlorophyll easily disintegrates. 5 In contrast, the high stability of copper chlorophyllins allows their application in the food industry, 6 catalysis, 7 and medicine. 8 The use of chlorophyllins is also supported by their high aqueous solubility.…”

Section: Introductionmentioning

confidence: 99%

The porphyrin center as a regulator for metal–ligand covalency and π hybridization in the entire molecule

Büchner

Fondell

Haverkamp

et al. 2021

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

show abstract

Chlorophyll derivatives as catalysts and comonomers for atom transfer radical polymerizations

Abstract: Derivatives of chlorophyll were investigated as both catalysts and comonomers to generate well-defined polymers with narrow dispersities under AGET ATRP conditions.

Cited by 16 publications

References 78 publications

Peroxidase Activity of Myoglobin Variants Reconstituted with Artificial Cofactors

Peroxidase Activity of Myoglobin Variants Reconstituted with Artificial Cofactors

Biopolymer Films of Metal-Coordinated Chlorophyll-a Derivatives for “Green” Supercapacitor Electrodes

The porphyrin center as a regulator for metal–ligand covalency and π hybridization in the entire molecule

Contact Info

Product

Resources

About