Molecularly defined caprolactone oligomers and polymers: synthesis and characterization.
Identifieur interne : 002964 ( Main/Exploration ); précédent : 002963; suivant : 002965Molecularly defined caprolactone oligomers and polymers: synthesis and characterization.
Auteurs : Kenichi Takizawa [États-Unis] ; Chuanbing Tang ; Craig J. HawkerSource :
- Journal of the American Chemical Society [ 1520-5126 ] ; 2008.
Descripteurs français
- KwdFr :
- Calorimétrie différentielle à balayage, Caproates (), Caproates (synthèse chimique), Lactones (), Lactones (synthèse chimique), Microscopie à force atomique, Polymères (), Polymères (synthèse chimique), Spectrométrie de masse ESI, Spectrométrie de masse MALDI, Spectroscopie par résonance magnétique, Structure moléculaire.
- MESH :
English descriptors
- KwdEn :
- Calorimetry, Differential Scanning, Caproates (chemical synthesis), Caproates (chemistry), Lactones (chemical synthesis), Lactones (chemistry), Magnetic Resonance Spectroscopy, Microscopy, Atomic Force, Molecular Structure, Polymers (chemical synthesis), Polymers (chemistry), Spectrometry, Mass, Electrospray Ionization, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization.
- MESH :
- chemical , chemical synthesis : Caproates, Lactones, Polymers.
- chemical , chemistry : Caproates, Lactones, Polymers.
- Calorimetry, Differential Scanning, Magnetic Resonance Spectroscopy, Microscopy, Atomic Force, Molecular Structure, Spectrometry, Mass, Electrospray Ionization, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization.
Abstract
The synthesis of molecularly defined epsilon-caprolactone oligomers and polymers up to the 64-mer, via an exponential growth strategy, is described. By careful selection of orthogonal protecting groups, t-butyldimethylsilyl (TBDMS) ether for the hydroxyl group and benzyl (Bn) ester for the carboxylic acid group, a highly efficient synthetic strategy was developed with yields for both deprotection steps being essentially quantitative and for the coupling reactions using 1,3-dicyclohexylcarbodiimide (DCC), yields of 80-95% were obtained even at high molecular weights. This allows monodisperse dimers, tetramers, octamers, 16-mers, 32-mers and 64-mers to be prepared in gram quantities and fully characterized using mass spectroscopy, size exclusion chromatography (SEC), and IR and NMR spectroscopy. Thermal and physical properties were measured using thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), atomic force microscopy (AFM), and small-angle X-ray scattering (SAXS). These results conclusively show a distinct structure/property relationship with a close correlation between the number of repeat units and physical properties. In addition, a number of marked differences were observed on comparison with the parent poly(caprolactone) polymer.
DOI: 10.1021/ja077149w
PubMed: 18189397
Affiliations:
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Hawker</name></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="eISSN">1520-5126</idno><imprint><date when="2008" type="published">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Calorimetry, Differential Scanning</term><term>Caproates (chemical synthesis)</term><term>Caproates (chemistry)</term><term>Lactones (chemical synthesis)</term><term>Lactones (chemistry)</term><term>Magnetic Resonance Spectroscopy</term><term>Microscopy, Atomic Force</term><term>Molecular Structure</term><term>Polymers (chemical synthesis)</term><term>Polymers (chemistry)</term><term>Spectrometry, Mass, Electrospray Ionization</term><term>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Calorimétrie différentielle à balayage</term><term>Caproates ()</term><term>Caproates (synthèse chimique)</term><term>Lactones ()</term><term>Lactones (synthèse chimique)</term><term>Microscopie à force atomique</term><term>Polymères ()</term><term>Polymères (synthèse chimique)</term><term>Spectrométrie de masse ESI</term><term>Spectrométrie de masse MALDI</term><term>Spectroscopie par résonance magnétique</term><term>Structure moléculaire</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Caproates</term><term>Lactones</term><term>Polymers</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Caproates</term><term>Lactones</term><term>Polymers</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Caproates</term><term>Lactones</term><term>Polymères</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Calorimetry, Differential Scanning</term><term>Magnetic Resonance Spectroscopy</term><term>Microscopy, Atomic Force</term><term>Molecular Structure</term><term>Spectrometry, Mass, Electrospray Ionization</term><term>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Calorimétrie différentielle à balayage</term><term>Caproates</term><term>Lactones</term><term>Microscopie à force atomique</term><term>Polymères</term><term>Spectrométrie de masse ESI</term><term>Spectrométrie de masse MALDI</term><term>Spectroscopie par résonance magnétique</term><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The synthesis of molecularly defined epsilon-caprolactone oligomers and polymers up to the 64-mer, via an exponential growth strategy, is described. By careful selection of orthogonal protecting groups, t-butyldimethylsilyl (TBDMS) ether for the hydroxyl group and benzyl (Bn) ester for the carboxylic acid group, a highly efficient synthetic strategy was developed with yields for both deprotection steps being essentially quantitative and for the coupling reactions using 1,3-dicyclohexylcarbodiimide (DCC), yields of 80-95% were obtained even at high molecular weights. This allows monodisperse dimers, tetramers, octamers, 16-mers, 32-mers and 64-mers to be prepared in gram quantities and fully characterized using mass spectroscopy, size exclusion chromatography (SEC), and IR and NMR spectroscopy. Thermal and physical properties were measured using thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), atomic force microscopy (AFM), and small-angle X-ray scattering (SAXS). These results conclusively show a distinct structure/property relationship with a close correlation between the number of repeat units and physical properties. In addition, a number of marked differences were observed on comparison with the parent poly(caprolactone) polymer.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country></list><tree><noCountry><name sortKey="Hawker, Craig J" sort="Hawker, Craig J" uniqKey="Hawker C" first="Craig J" last="Hawker">Craig J. Hawker</name><name sortKey="Tang, Chuanbing" sort="Tang, Chuanbing" uniqKey="Tang C" first="Chuanbing" last="Tang">Chuanbing Tang</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Takizawa, Kenichi" sort="Takizawa, Kenichi" uniqKey="Takizawa K" first="Kenichi" last="Takizawa">Kenichi Takizawa</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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