Optically active polymethacrylamides bearing a bulky oxazoline pendant: Synthesis and characterization
A novel type of chiral methacrylamide derivatives, N-[ o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide (( R)-PhOPMAM), N-[ o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide (( S)-Pr i OPMAM), and N-[ o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide (( S)-...
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| Veröffentlicht in: | Reactive & functional polymers 2007-07, Vol.67 (7), p.636-643 |
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| creator | Fu, Zheng Xi, Xiujuan Jiang, Liming Shen, Zhiquan |
| description | A novel type of chiral methacrylamide derivatives,
N-[
o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
R)-PhOPMAM),
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-Pr
i
OPMAM), and
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-MeOPMAM), was synthesized and radically polymerized to the corresponding polymers in moderate yields. The polymerization characteristics and the chiroptical behavior of the resultant polymers have been examined in detail by using circular dichroism (CD), UV–Vis, and NMR spectroscopies in comparison with our previous observation. It was found that the oxazoline moieties have an effective influence on both the polymerization process and the optical activity of obtained polymers. Especially, the levorotatory monomer (
S)-MeOPMAM
(
[
α
]
D
25
=
-
7.7
°
)
was transformed to the polymers with dextrorotation activity
(
[
α
]
D
25
=
+
102.0
°
to
+
117.1
°
)
, indicating the polymer main chain might exist a helical conformation. Also, the chiral recognition ability was briefly evaluated by
1H NMR technique for the poly(OPMAM)s. |
| doi_str_mv | 10.1016/j.reactfunctpolym.2007.04.005 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_30066410</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S1381514807000727</els_id><sourcerecordid>30066410</sourcerecordid><originalsourceid>FETCH-LOGICAL-c394t-f56ee23f3b7dc00df638eef7c044d1e0354da65c074da5e2a636775bc2c3453f3</originalsourceid><addsrcrecordid>eNqNkDFvFDEQhbcAiRD4D25Cd8t47fVekChQBAEpUgqgtubGY86Hz3vYvojNr4_DRUKioprme-9pvq67kNBLkObtrs-MVP0xUT3Mcdn3A8DUg-4BxmfdmVRruRqlXr_oXpayA5CTNOas87eHGghjXESLhzsWf9Jct0h5ibgPjovYMOaQfggUm2P8uYj5N97PMaRGc3KY6jvxdUl1yyUUgckJ2mJufZzDPdYwp1fdc4-x8Oune959__Tx29Xn1c3t9ZerDzcrUpe6rvxomAfl1WZyBOC8UWtmPxFo7SSDGrVDMxJM7Y48oFFmmsYNDaT02HLn3ZtT7yHPv45cqt2HQhwjJp6PxSoAY7SEBr4_gZTnUjJ7e8hhj3mxEuyjUbuz_xi1j0YtaNuMtvzF0xCWps9nTBTK35L1pTTToBp3feK4fX0XONtCgROxC5mpWjeH_1x8ABpZm74</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>30066410</pqid></control><display><type>article</type><title>Optically active polymethacrylamides bearing a bulky oxazoline pendant: Synthesis and characterization</title><source>Elsevier ScienceDirect Journals</source><creator>Fu, Zheng ; Xi, Xiujuan ; Jiang, Liming ; Shen, Zhiquan</creator><creatorcontrib>Fu, Zheng ; Xi, Xiujuan ; Jiang, Liming ; Shen, Zhiquan</creatorcontrib><description>A novel type of chiral methacrylamide derivatives,
N-[
o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
R)-PhOPMAM),
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-Pr
i
OPMAM), and
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-MeOPMAM), was synthesized and radically polymerized to the corresponding polymers in moderate yields. The polymerization characteristics and the chiroptical behavior of the resultant polymers have been examined in detail by using circular dichroism (CD), UV–Vis, and NMR spectroscopies in comparison with our previous observation. It was found that the oxazoline moieties have an effective influence on both the polymerization process and the optical activity of obtained polymers. Especially, the levorotatory monomer (
S)-MeOPMAM
(
[
α
]
D
25
=
-
7.7
°
)
was transformed to the polymers with dextrorotation activity
(
[
α
]
D
25
=
+
102.0
°
to
+
117.1
°
)
, indicating the polymer main chain might exist a helical conformation. Also, the chiral recognition ability was briefly evaluated by
1H NMR technique for the poly(OPMAM)s.</description><identifier>ISSN: 1381-5148</identifier><identifier>DOI: 10.1016/j.reactfunctpolym.2007.04.005</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Applied sciences ; Exact sciences and technology ; Methacrylamides ; Optical activity ; Organic polymers ; Oxazoline ; Physicochemistry of polymers ; Polymerization ; Preparation, kinetics, thermodynamics, mechanism and catalysts ; Radical polymerization</subject><ispartof>Reactive & functional polymers, 2007-07, Vol.67 (7), p.636-643</ispartof><rights>2007 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c394t-f56ee23f3b7dc00df638eef7c044d1e0354da65c074da5e2a636775bc2c3453f3</citedby><cites>FETCH-LOGICAL-c394t-f56ee23f3b7dc00df638eef7c044d1e0354da65c074da5e2a636775bc2c3453f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S1381514807000727$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18916723$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Fu, Zheng</creatorcontrib><creatorcontrib>Xi, Xiujuan</creatorcontrib><creatorcontrib>Jiang, Liming</creatorcontrib><creatorcontrib>Shen, Zhiquan</creatorcontrib><title>Optically active polymethacrylamides bearing a bulky oxazoline pendant: Synthesis and characterization</title><title>Reactive & functional polymers</title><description>A novel type of chiral methacrylamide derivatives,
N-[
o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
R)-PhOPMAM),
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-Pr
i
OPMAM), and
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-MeOPMAM), was synthesized and radically polymerized to the corresponding polymers in moderate yields. The polymerization characteristics and the chiroptical behavior of the resultant polymers have been examined in detail by using circular dichroism (CD), UV–Vis, and NMR spectroscopies in comparison with our previous observation. It was found that the oxazoline moieties have an effective influence on both the polymerization process and the optical activity of obtained polymers. Especially, the levorotatory monomer (
S)-MeOPMAM
(
[
α
]
D
25
=
-
7.7
°
)
was transformed to the polymers with dextrorotation activity
(
[
α
]
D
25
=
+
102.0
°
to
+
117.1
°
)
, indicating the polymer main chain might exist a helical conformation. Also, the chiral recognition ability was briefly evaluated by
1H NMR technique for the poly(OPMAM)s.</description><subject>Applied sciences</subject><subject>Exact sciences and technology</subject><subject>Methacrylamides</subject><subject>Optical activity</subject><subject>Organic polymers</subject><subject>Oxazoline</subject><subject>Physicochemistry of polymers</subject><subject>Polymerization</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Radical polymerization</subject><issn>1381-5148</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNqNkDFvFDEQhbcAiRD4D25Cd8t47fVekChQBAEpUgqgtubGY86Hz3vYvojNr4_DRUKioprme-9pvq67kNBLkObtrs-MVP0xUT3Mcdn3A8DUg-4BxmfdmVRruRqlXr_oXpayA5CTNOas87eHGghjXESLhzsWf9Jct0h5ibgPjovYMOaQfggUm2P8uYj5N97PMaRGc3KY6jvxdUl1yyUUgckJ2mJufZzDPdYwp1fdc4-x8Oune959__Tx29Xn1c3t9ZerDzcrUpe6rvxomAfl1WZyBOC8UWtmPxFo7SSDGrVDMxJM7Y48oFFmmsYNDaT02HLn3ZtT7yHPv45cqt2HQhwjJp6PxSoAY7SEBr4_gZTnUjJ7e8hhj3mxEuyjUbuz_xi1j0YtaNuMtvzF0xCWps9nTBTK35L1pTTToBp3feK4fX0XONtCgROxC5mpWjeH_1x8ABpZm74</recordid><startdate>20070701</startdate><enddate>20070701</enddate><creator>Fu, Zheng</creator><creator>Xi, Xiujuan</creator><creator>Jiang, Liming</creator><creator>Shen, Zhiquan</creator><general>Elsevier B.V</general><general>Elsevier Science</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20070701</creationdate><title>Optically active polymethacrylamides bearing a bulky oxazoline pendant: Synthesis and characterization</title><author>Fu, Zheng ; Xi, Xiujuan ; Jiang, Liming ; Shen, Zhiquan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c394t-f56ee23f3b7dc00df638eef7c044d1e0354da65c074da5e2a636775bc2c3453f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Applied sciences</topic><topic>Exact sciences and technology</topic><topic>Methacrylamides</topic><topic>Optical activity</topic><topic>Organic polymers</topic><topic>Oxazoline</topic><topic>Physicochemistry of polymers</topic><topic>Polymerization</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Radical polymerization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fu, Zheng</creatorcontrib><creatorcontrib>Xi, Xiujuan</creatorcontrib><creatorcontrib>Jiang, Liming</creatorcontrib><creatorcontrib>Shen, Zhiquan</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Reactive & functional polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fu, Zheng</au><au>Xi, Xiujuan</au><au>Jiang, Liming</au><au>Shen, Zhiquan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Optically active polymethacrylamides bearing a bulky oxazoline pendant: Synthesis and characterization</atitle><jtitle>Reactive & functional polymers</jtitle><date>2007-07-01</date><risdate>2007</risdate><volume>67</volume><issue>7</issue><spage>636</spage><epage>643</epage><pages>636-643</pages><issn>1381-5148</issn><abstract>A novel type of chiral methacrylamide derivatives,
N-[
o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
R)-PhOPMAM),
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-Pr
i
OPMAM), and
N-[
o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]methacrylamide ((
S)-MeOPMAM), was synthesized and radically polymerized to the corresponding polymers in moderate yields. The polymerization characteristics and the chiroptical behavior of the resultant polymers have been examined in detail by using circular dichroism (CD), UV–Vis, and NMR spectroscopies in comparison with our previous observation. It was found that the oxazoline moieties have an effective influence on both the polymerization process and the optical activity of obtained polymers. Especially, the levorotatory monomer (
S)-MeOPMAM
(
[
α
]
D
25
=
-
7.7
°
)
was transformed to the polymers with dextrorotation activity
(
[
α
]
D
25
=
+
102.0
°
to
+
117.1
°
)
, indicating the polymer main chain might exist a helical conformation. Also, the chiral recognition ability was briefly evaluated by
1H NMR technique for the poly(OPMAM)s.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.reactfunctpolym.2007.04.005</doi><tpages>8</tpages></addata></record> |
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| issn | 1381-5148 |
| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Applied sciences Exact sciences and technology Methacrylamides Optical activity Organic polymers Oxazoline Physicochemistry of polymers Polymerization Preparation, kinetics, thermodynamics, mechanism and catalysts Radical polymerization |
| title | Optically active polymethacrylamides bearing a bulky oxazoline pendant: Synthesis and characterization |
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