Catalytically Active Multicompartment Micelles

Eman Ahmed, Jinwon Cho, Lulu Friedmann, Seung Soon Jang, Marcus Weck

Research output: Contribution to journalArticlepeer-review

Abstract

This article presents the self-assembly behavior of multicompartment micelles (MCMs) in water into morphologies with multiple segregated domains and their use as supports for aqueous catalysis. A library of poly(norbornene)-based amphiphilic bottlebrush copolymers containing covalently attached l-proline in the hydrophobic, styrene, and pentafluorostyrene domains and a poly(ethylene glycol)-containing repeat unit as the hydrophilic block have been synthesized using ring-opening metathesis polymerization. Interaction parameter (χ) values between amphiphilic blocks were determined using a Flory-Huggins-based computational model. The morphologies of the MCMs are observed via cryogenic transmission electron microscopy and modeled using dissipative particle dynamic simulations. The catalytic activities of these MCM nanoreactors were systematically investigated using the aldol addition between 4-nitrobenzaldehyde and cyclohexanone in water as a model reaction. MCMs present an ideal environment for catalysis by providing control over water content and enhancing interactions between the catalytic sites and the aldehyde substrate, thereby forming the aldol product in high yields and selectivities that is otherwise not possible under aqueous conditions. Catalyst location, block ratio, and functionality have substantial influences on micelle morphology and, ultimately, catalytic efficiency. "Clover-like"and "core-shell"micelle morphologies displayed the best catalytic activity. Our MCM-based catalytic system expands the application of these nanostructures beyond selective storage of guest molecules and demonstrates the importance of micelle morphology on catalytic activity.

Original languageEnglish (US)
Pages (from-to)2316-2326
Number of pages11
JournalJournal of the American Chemical Society
Volume2
Issue number10
DOIs
StatePublished - Oct 24 2022

Keywords

  • amphiphilic bottlebrush copolymer
  • asymmetric aldol addition
  • micelle morphology
  • multicompartment micelles
  • site isolation
  • supported catalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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