Studying the activity of the MacMillan catalyst embedded within hydrophobic cross-linked polymeric nanostructures

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Studying the activity of the MacMillan catalyst embedded within hydrophobic cross-linked polymeric nanostructures. / Moore, Beth L.; Moatsou, Dafni; Lu, Annhelen; O'Reilly, Rachel K.

In: Polymer Chemistry, Vol. 5, No. 10, 17.03.2014, p. 3487-3494.

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@article{3aca324ba9b44e8f8c8a7b337876ba4a,
title = "Studying the activity of the MacMillan catalyst embedded within hydrophobic cross-linked polymeric nanostructures",
abstract = "The immobilization of the MacMillan catalyst within a unique hydrophobic environment created by a lightly cross-linked nanogel structure and its resulting catalytic activity is reported. The catalytic activity and selectivity of the catalyst were evaluated using the Diels–Alder (DA) reaction between cyclopentadiene and cinnamaldehyde. The relatively easy synthetic route applied allowed for the synthesis of a collection of nanogels with catalyst incorporations ranging from 0.5 to 25 wt%. In addition, core–shell type nanogels were synthesized to evaluate potential recovery and reuse of the catalytic system. The influence of the concentrator effect and possible partition coefficient on the catalyst activity was investigated. The results indicate catalyst loading/concentration can be more significantly reduced when the catalyst is embedded within the polymeric nanostructures compared to the small molecule equivalent.",
keywords = "Diels-Alder reactions, organic catalysis, chiral imidazolidin-4-one, acylation reactions, immoblization, nanoreactors, core, organocatalysts, strategies, micelles",
author = "Moore, {Beth L.} and Dafni Moatsou and Annhelen Lu and O'Reilly, {Rachel K.}",
year = "2014",
month = mar,
day = "17",
doi = "10.1039/c3py01734f",
language = "English",
volume = "5",
pages = "3487--3494",
journal = "Polymer Chemistry",
issn = "1759-9954",
publisher = "Royal Society of Chemistry",
number = "10",

}

RIS

TY - JOUR

T1 - Studying the activity of the MacMillan catalyst embedded within hydrophobic cross-linked polymeric nanostructures

AU - Moore, Beth L.

AU - Moatsou, Dafni

AU - Lu, Annhelen

AU - O'Reilly, Rachel K.

PY - 2014/3/17

Y1 - 2014/3/17

N2 - The immobilization of the MacMillan catalyst within a unique hydrophobic environment created by a lightly cross-linked nanogel structure and its resulting catalytic activity is reported. The catalytic activity and selectivity of the catalyst were evaluated using the Diels–Alder (DA) reaction between cyclopentadiene and cinnamaldehyde. The relatively easy synthetic route applied allowed for the synthesis of a collection of nanogels with catalyst incorporations ranging from 0.5 to 25 wt%. In addition, core–shell type nanogels were synthesized to evaluate potential recovery and reuse of the catalytic system. The influence of the concentrator effect and possible partition coefficient on the catalyst activity was investigated. The results indicate catalyst loading/concentration can be more significantly reduced when the catalyst is embedded within the polymeric nanostructures compared to the small molecule equivalent.

AB - The immobilization of the MacMillan catalyst within a unique hydrophobic environment created by a lightly cross-linked nanogel structure and its resulting catalytic activity is reported. The catalytic activity and selectivity of the catalyst were evaluated using the Diels–Alder (DA) reaction between cyclopentadiene and cinnamaldehyde. The relatively easy synthetic route applied allowed for the synthesis of a collection of nanogels with catalyst incorporations ranging from 0.5 to 25 wt%. In addition, core–shell type nanogels were synthesized to evaluate potential recovery and reuse of the catalytic system. The influence of the concentrator effect and possible partition coefficient on the catalyst activity was investigated. The results indicate catalyst loading/concentration can be more significantly reduced when the catalyst is embedded within the polymeric nanostructures compared to the small molecule equivalent.

KW - Diels-Alder reactions

KW - organic catalysis

KW - chiral imidazolidin-4-one

KW - acylation reactions

KW - immoblization

KW - nanoreactors

KW - core

KW - organocatalysts

KW - strategies

KW - micelles

UR - http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=ORCID&SrcApp=OrcidOrg&DestLinkType=FullRecord&DestApp=WOS_CPL&KeyUT=WOS:000334833900024&KeyUID=WOS:000334833900024

U2 - 10.1039/c3py01734f

DO - 10.1039/c3py01734f

M3 - Article

VL - 5

SP - 3487

EP - 3494

JO - Polymer Chemistry

JF - Polymer Chemistry

SN - 1759-9954

IS - 10

ER -