Peptide‐based Organocatalyst on Stage: Functionalizing Mesoporous Silica by Tetrazine‐Norbornene Ligation

Brand, Raoul D.; Busche, Stefan; Börner, Hans G.; Smarsly, Bernd M.

doi:10.1002/cctc.202300778

Cited by 3 publications

(2 citation statements)

References 64 publications

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“…Heterogeneous batch catalysis [46] : N-butanal (10) (119 μL, 1.32 mmol, 3.0 eq.) and β-nitrostyrene (11) (65 mg, 0.44 mmol, 1.0 eq.)…”

Section: Catalytic Testsmentioning

confidence: 99%

“…[40,41] Considering that materials science applications and high surface area material transformations will ultimately require scalable, catalyst-free ligations, the inverse electron-demand Diels-Alder (IEDDA) [42] ligation holds promise as a powerful PSM strategy. While IEDDA chemistries have been used to modify quantum dots, DNA, polymers, silica particles, metal-organic frameworks and hydrogel microspheres, [43][44][45][46][47][48][49] the ligation of norbornene (Nor) derivatives with an asymmetric 1,2,4,5-tetrazine (Tz) moiety benefits from a Nor stability [50] coupled with a simplified one-pot Tz synthesis. [51] The Nor/Tzligation appears to be suitable for the functionalization of high surface area MPNs.…”

Section: Introductionmentioning

confidence: 99%

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Ligating Catalytically Active Peptides onto Microporous Polymers: A General Route Toward Specifically‐Functional High Surface Area Platforms

Busche,

Traxler,

Thomas

et al. 2023

ChemSusChem

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A versatile post‐synthetic modification strategy to functionalize a high surface area microporous network (MPN‐OH) by bioorthogonal inverse electron‐demand Diels‐Alder (IEDDA) ligation is presented. While the polymer matrix is modified with a readily accessible norbornene isocyanate (Nb‐NCO), a set of functional entities, presenting the robust asymmetric 1,2,4,5‐tetrazine (Tz) allows easy functionalization of the MPN by chemoselective Nb/Tz ligation. A generic route is demonstrated, modulating the internal interfaces by introducing carboxylates, amides or amino acids as well as an oligopeptide d‐Pro‐Pro‐Glu organocatalyst. The MPN‐Peptide construct largely retains the catalytic activity and selectivity in an enantioselective enamine catalysis, proving remarkable availability in different solvents, offers heterogeneous organocatalysis in bulk and shows stability in recycling settings.

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“…Heterogeneous batch catalysis [46] : N-butanal (10) (119 μL, 1.32 mmol, 3.0 eq.) and β-nitrostyrene (11) (65 mg, 0.44 mmol, 1.0 eq.)…”

Section: Catalytic Testsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ligating Catalytically Active Peptides onto Microporous Polymers: A General Route Toward Specifically‐Functional High Surface Area Platforms

Busche,

Traxler,

Thomas

et al. 2023

ChemSusChem

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Heavy metal on stage: Making ion-exchange resin selective by peptide tetrazine-norbornene ligation

Busche,

Vigarani,

Retzmann

et al. 2024

Polymer

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Enhanced Recyclability of Polymer Brush-Supported Sulfonic Acid with Diblock Architecture

Zhao,

Cui,

Zhang

et al. 2024

ACS Appl. Polym. Mater.

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Solid polymer brush-supported molecular catalysts generally exhibit activity comparable to molecular catalysts, but they suffer the problems of decreased activity with increasing recycled times in reactions. This study explores the use of polymer brushes with a diblock architecture to design durable silica-based polymer brush-supported sulfonic acid catalysts. Two silica-based polymer brush materials, differing in the amounts of polystyrene (PS) brush, were prepared by first growing PS brush using copper-catalyzed ARGET SI-ATRP and growing poly(vinylimidazole) using SI-ATRP. The resulting polymer brushes were then reacted with 1,3-propane sultone and trifluoromethanesulfonic acid to obtain two solid acid catalysts. For comparison, a solid sulfonic acid without a PS layer was also prepared. These solid acidic catalysts were applied to synthesize acylals from aldehydes and acetic anhydride. The polymer brush-supported acids demonstrated superior activity compared with the molecular catalyst. Notably, the catalyst with PS protection could be recycled 15 times (yield ≥95%) without a decrease in activity; in contrast, the yield of the catalyst without PS protection decreased to 35% in the 10th run. Thermogravimetric analysis indicated 3% loss of materials for the catalyst with the PS layer and 9.5% loss for the catalyst without the PS layer, after the specified numbers of runs. Polymer brush protection probably finds more applications in the design of more durable solid-based polymer brush-supported molecular catalysts.

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Peptide‐based Organocatalyst on Stage: Functionalizing Mesoporous Silica by Tetrazine‐Norbornene Ligation

Cited by 3 publications

References 64 publications

Ligating Catalytically Active Peptides onto Microporous Polymers: A General Route Toward Specifically‐Functional High Surface Area Platforms

Ligating Catalytically Active Peptides onto Microporous Polymers: A General Route Toward Specifically‐Functional High Surface Area Platforms

Heavy metal on stage: Making ion-exchange resin selective by peptide tetrazine-norbornene ligation

Enhanced Recyclability of Polymer Brush-Supported Sulfonic Acid with Diblock Architecture

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