Synthesis and solid state structure of fluorous probe molecules for fluorous separation applications

H.-J Lehmler; S Telu; S.M Vyas; N.S Shaikh; S.E Rankin; B.L Knutson; S Parkin

doi:10.1016/j.tet.2010.02.018

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Synthesis and solid state structure of fluorous probe molecules for fluorous separation applications

Journal article

Peer reviewed

Synthesis and solid state structure of fluorous probe molecules for fluorous separation applications

H.-J Lehmler, S Telu, S.M Vyas, N.S Shaikh, S.E Rankin, B.L Knutson and S Parkin

Tetrahedron, Vol.66(14), pp.2561-2569

2010

DOI: 10.1016/j.tet.2010.02.018

PMCID: PMC2840617

PMID: 20305832

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Abstract

A series of colored hydrocarbon and fluorocarbon tagged 1-fluoro-4-alkylamino-anthraquinones and 1,4-bis-alkylamino-anthraquinone probe molecules were synthesized from a (fluorinated) alkyl amine and 1,4-difluoroanthraquinone to aid in the development of fluorous separation applications. The anthraquinones displayed stacking of the anthraquinone tricycle and interdigitation of the (fluorinated) alkyl chains in the solid state. Furthermore, intramolecular N–H⋯O hydrogen bonds forced the hydrocarbon and fluorocarbon tags into a conformation pointing away from the anthraquinone tricycle, with the angle of the tricycle plane normal and the main (fluorinated) alkyl vector ranging from 1° to 39°. Separation of the probe molecules on fluorous silica gel showed that the degree of fluorination of the probe molecules plays only a minor role with most eluents (e.g., hexane/ethyl acetate and methyl nonafluorobutyl ethers/ethyl acetate). However, toluene as eluent caused a pronounced separation by degree of fluorination for fluorocarbon, but not hydrocarbon tagged probe molecules on both silica gel and fluorous silica gel. These studies suggest that hydrocarbon and fluorocarbon tagged anthraquinones are useful probe molecules for the development of laboratory scale fluorous separation applications. [Display omitted]

Fluorophilic probes

Fluorous separations

Anthraquinones

Fluorophilicity

Details

Title: Subtitle: Synthesis and solid state structure of fluorous probe molecules for fluorous separation applications
Creators: H.-J Lehmler - Department of Occupational and Environmental Health, University of Iowa, College of Public Health, 100 Oakdale Campus, 221 IREH, Iowa City, IA 52242-5000, USA
S Telu - Department of Occupational and Environmental Health, University of Iowa, College of Public Health, 100 Oakdale Campus, 221 IREH, Iowa City, IA 52242-5000, USA
S.M Vyas - Department of Occupational and Environmental Health, University of Iowa, College of Public Health, 100 Oakdale Campus, 221 IREH, Iowa City, IA 52242-5000, USA
N.S Shaikh - Department of Occupational and Environmental Health, University of Iowa, College of Public Health, 100 Oakdale Campus, 221 IREH, Iowa City, IA 52242-5000, USA
S.E Rankin - Chemical and Materials Engineering Department, University of Kentucky, Lexington, KY 40506, USA
B.L Knutson - Chemical and Materials Engineering Department, University of Kentucky, Lexington, KY 40506, USA
S Parkin - Department of Chemistry, University of Kentucky, Lexington, KY 40536, USA
Resource Type: Journal article
Publication Details: Tetrahedron, Vol.66(14), pp.2561-2569
DOI: 10.1016/j.tet.2010.02.018
PMID: 20305832
PMCID: PMC2840617
NLM abbreviation: Tetrahedron
ISSN: 0040-4020
eISSN: 1464-5416
Publisher: Elsevier Ltd
Language: English
Date published: 2010
Academic Unit: Occupational and Environmental Health; Iowa Neuroscience Institute; Iowa Superfund Research Program
Record Identifier: 9984001081002771

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