Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores
Novel optically-active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (based on the l-lactic acid residue) linked to the spiropyran chromophore, have been successfully synthesized and fully characterized. These intrinsically chiral polymers e...
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| Veröffentlicht in: | Reactive & functional polymers 2012-07, Vol.72 (7), p.469-477 |
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| container_title | Reactive & functional polymers |
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| creator | Angiolini, Luigi Benelli, Tiziana Bicciocchi, Erika Giorgini, Loris Raymo, Françisco M. |
| description | Novel optically-active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (based on the l-lactic acid residue) linked to the spiropyran chromophore, have been successfully synthesized and fully characterized.
These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperatures in the range 100–130°C and decomposition temperatures around 270°C. The chiroptical characterization indicates the occurrence of asymmetric induction on the electronic transitions of the side-chain chromophore related to the number of l-lactic acid residues interposed between the main chain and the spiropyran chromophore.
In the presence of acid, these systems can be used to modulate the protonation of polymeric azopyridine moieties upon photoisomerization of the spiropyran group. In addition to UV–Vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, the system thus behaving as a chiroptical switch. |
| doi_str_mv | 10.1016/j.reactfunctpolym.2012.04.011 |
| format | Article |
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These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperatures in the range 100–130°C and decomposition temperatures around 270°C. The chiroptical characterization indicates the occurrence of asymmetric induction on the electronic transitions of the side-chain chromophore related to the number of l-lactic acid residues interposed between the main chain and the spiropyran chromophore.
In the presence of acid, these systems can be used to modulate the protonation of polymeric azopyridine moieties upon photoisomerization of the spiropyran group. In addition to UV–Vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, the system thus behaving as a chiroptical switch.</description><identifier>ISSN: 1381-5148</identifier><identifier>DOI: 10.1016/j.reactfunctpolym.2012.04.011</identifier><language>eng</language><publisher>Kidlington: Elsevier B.V</publisher><subject>Applied sciences ; Bearing ; Chains (polymeric) ; Chromophores ; Circular dichroism ; Exact sciences and technology ; Optical activity ; Organic polymers ; Photochromic chiral polymers ; Photochromism ; Physicochemistry of polymers ; Polymeric chiroptical switches ; Polymers ; Polymers with particular properties ; Preparation, kinetics, thermodynamics, mechanism and catalysts ; Residues ; Spiropyrans ; Synthesis</subject><ispartof>Reactive & functional polymers, 2012-07, Vol.72 (7), p.469-477</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c396t-9737621180a3402328feb4092782d5198bed90834fdc35a3ac3f2218cae0bf233</citedby><cites>FETCH-LOGICAL-c396t-9737621180a3402328feb4092782d5198bed90834fdc35a3ac3f2218cae0bf233</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S1381514812001228$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25982017$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Angiolini, Luigi</creatorcontrib><creatorcontrib>Benelli, Tiziana</creatorcontrib><creatorcontrib>Bicciocchi, Erika</creatorcontrib><creatorcontrib>Giorgini, Loris</creatorcontrib><creatorcontrib>Raymo, Françisco M.</creatorcontrib><title>Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores</title><title>Reactive & functional polymers</title><description>Novel optically-active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (based on the l-lactic acid residue) linked to the spiropyran chromophore, have been successfully synthesized and fully characterized.
These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperatures in the range 100–130°C and decomposition temperatures around 270°C. The chiroptical characterization indicates the occurrence of asymmetric induction on the electronic transitions of the side-chain chromophore related to the number of l-lactic acid residues interposed between the main chain and the spiropyran chromophore.
In the presence of acid, these systems can be used to modulate the protonation of polymeric azopyridine moieties upon photoisomerization of the spiropyran group. In addition to UV–Vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, the system thus behaving as a chiroptical switch.</description><subject>Applied sciences</subject><subject>Bearing</subject><subject>Chains (polymeric)</subject><subject>Chromophores</subject><subject>Circular dichroism</subject><subject>Exact sciences and technology</subject><subject>Optical activity</subject><subject>Organic polymers</subject><subject>Photochromic chiral polymers</subject><subject>Photochromism</subject><subject>Physicochemistry of polymers</subject><subject>Polymeric chiroptical switches</subject><subject>Polymers</subject><subject>Polymers with particular properties</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Residues</subject><subject>Spiropyrans</subject><subject>Synthesis</subject><issn>1381-5148</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqNkD2P1DAQQFOAxHHwH9ycRJPgj2ziFBToBAfSSRRAbXknY-JVYgePd6WU_HMc9kRBRWVZfp6neVV1J3gjuOjenpqEFrI7B8hrnLelkVzIhrcNF-JZdSOUFvVBtPpF9ZLoxLnoRdfdVL--biFPSJ6YDSNbp5hjQlpjIH9BdsTJXnxMLDoW1-zBzvPGimh_XDBPFtI2e2BTXOIfLyZiEEO2Pvjwg5EfsYap3BitPsV1SzYwmNLOT7vqVfXc2Znw9dN5W33_-OHb_af68cvD5_v3jzWoocv10Ku-k0JoblXLpZLa4bHlg-y1HA9i0EccB65V60ZQB6ssKCel0GCRH51U6rZ6c527pvjzjJTN4glwnm3AeCYjuNKy1VoPBX13RSFFooTOrMkvNm0FMntuczL_5DZ7bsNbU3KX_3dPKkulmCsrg6e_Q-Rh0AXvC_dw5bDsffGYDIHHADj6hJDNGP1_Gn8DuuCmRQ</recordid><startdate>20120701</startdate><enddate>20120701</enddate><creator>Angiolini, Luigi</creator><creator>Benelli, Tiziana</creator><creator>Bicciocchi, Erika</creator><creator>Giorgini, Loris</creator><creator>Raymo, Françisco M.</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20120701</creationdate><title>Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores</title><author>Angiolini, Luigi ; Benelli, Tiziana ; Bicciocchi, Erika ; Giorgini, Loris ; Raymo, Françisco M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-9737621180a3402328feb4092782d5198bed90834fdc35a3ac3f2218cae0bf233</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Applied sciences</topic><topic>Bearing</topic><topic>Chains (polymeric)</topic><topic>Chromophores</topic><topic>Circular dichroism</topic><topic>Exact sciences and technology</topic><topic>Optical activity</topic><topic>Organic polymers</topic><topic>Photochromic chiral polymers</topic><topic>Photochromism</topic><topic>Physicochemistry of polymers</topic><topic>Polymeric chiroptical switches</topic><topic>Polymers</topic><topic>Polymers with particular properties</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Residues</topic><topic>Spiropyrans</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Angiolini, Luigi</creatorcontrib><creatorcontrib>Benelli, Tiziana</creatorcontrib><creatorcontrib>Bicciocchi, Erika</creatorcontrib><creatorcontrib>Giorgini, Loris</creatorcontrib><creatorcontrib>Raymo, Françisco M.</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>Angiolini, Luigi</au><au>Benelli, Tiziana</au><au>Bicciocchi, Erika</au><au>Giorgini, Loris</au><au>Raymo, Françisco M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores</atitle><jtitle>Reactive & functional polymers</jtitle><date>2012-07-01</date><risdate>2012</risdate><volume>72</volume><issue>7</issue><spage>469</spage><epage>477</epage><pages>469-477</pages><issn>1381-5148</issn><abstract>Novel optically-active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (based on the l-lactic acid residue) linked to the spiropyran chromophore, have been successfully synthesized and fully characterized.
These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperatures in the range 100–130°C and decomposition temperatures around 270°C. The chiroptical characterization indicates the occurrence of asymmetric induction on the electronic transitions of the side-chain chromophore related to the number of l-lactic acid residues interposed between the main chain and the spiropyran chromophore.
In the presence of acid, these systems can be used to modulate the protonation of polymeric azopyridine moieties upon photoisomerization of the spiropyran group. In addition to UV–Vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, the system thus behaving as a chiroptical switch.</abstract><cop>Kidlington</cop><pub>Elsevier B.V</pub><doi>10.1016/j.reactfunctpolym.2012.04.011</doi><tpages>9</tpages></addata></record> |
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| subjects | Applied sciences Bearing Chains (polymeric) Chromophores Circular dichroism Exact sciences and technology Optical activity Organic polymers Photochromic chiral polymers Photochromism Physicochemistry of polymers Polymeric chiroptical switches Polymers Polymers with particular properties Preparation, kinetics, thermodynamics, mechanism and catalysts Residues Spiropyrans Synthesis |
| title | Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores |
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