Self-Assembled Thermoresponsive Molecular Brushes as Nanoreactors for Asymmetric Aldol Addition in Water

Kuepfert, Michael; Ahmed, Eman; Weck, Marcus

doi:10.1021/acs.macromol.0c02708

Self-Assembled Thermoresponsive Molecular Brushes as Nanoreactors for Asymmetric Aldol Addition in Water

Journal Article · Tue Apr 06 04:00:00 EDT 2021 · Macromolecules

DOI:https://doi.org/10.1021/acs.macromol.0c02708· OSTI ID:1772241

Kuepfert, Michael ^[1]; Ahmed, Eman ^[2]; ^[2]

New York Univ. (NYU), NY (United States); NYU
New York Univ. (NYU), NY (United States)

The manipulation and tunability of self-assembled block copolymers through external stimuli presents an attractive strategy to develop smart polymer-based nanoreactors as supports for non-orthogonal tandem catalysis. We report on thermoresponsive core-shell micelles based on poly[norbornene-poly(2-methyl-2-oxazoline-block-2-propyl-2-oxazoline)]-graft-poly[norbornene L-proline] (P[NB-P(MeOx-b-PropOx)]-graft-P[NB-L-proline]) as catalyst supports for L-proline. These molecular brushes exhibit large differences in lower critical solution temperature behavior and nanostructure size in water depending on the chain-lengths and proline connectivity. L-Proline-mediated aldol reactions expose the efficiency by which the molecular brushes self-assemble into micelles. Molecular brushes with an extended backbone show higher activity and selectivity, suggesting better core-shell segregation of the micelles and exclusion of water from the catalytic site. Catalytic efficiencies are not improved above the cloud point temperature, the catalytic be-havior is rather sensitive to conformational changes of the polymer chains.

View Accepted Manuscript (DOE)

Research Organization:: New York Univ. (NYU), NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-03ER15459

OSTI ID:: 1772241

Journal Information:: Macromolecules, Journal Name: Macromolecules Journal Issue: 8 Vol. 54; ISSN 0024-9297

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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