Titanium complexes bearing 2,6-Bis(o-hydroxyalkyl)pyridine ligands in the ring-opening polymerization of L-Lactide and ε-caprolactone
A series of titanium (Ti) compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized and investigated as catalysts for the ring-opening polymerization of ε-caprolactone (CL) and L-lactide (LA). The Ti complexes with electron-withdrawing groups in pyridine rings or steric bulky groups...
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| Veröffentlicht in: | Polymer (Guilford) 2020-09, Vol.204, p.122860, Article 122860 |
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| creator | Lai, Feng-Jie Huang, Tsai-Wen Chang, Yu-Lun Chang, Heng-Yi Lu, Wei-Yi Ding, Shangwu Chen, Hsuan-Ying Chiu, Chien-Chih Wu, Kuo-Hui |
| description | A series of titanium (Ti) compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized and investigated as catalysts for the ring-opening polymerization of ε-caprolactone (CL) and L-lactide (LA). The Ti complexes with electron-withdrawing groups in pyridine rings or steric bulky groups in hydroxymethyl groups reduced the catalytic activity in CL and LA polymerizations, and MeLPh-TiOPr2 exhibited the highest catalytic activity ([CL] = 0.5 M, [CL]:[Cat] = 100:8, 60 °C, 7.5 h, conversion = 93%; [LA] = 0.5 M, [LA]:[Cat] = 100:8, 60 °C, 3.5 h, conversion = 98%). The density functional theory calculation results revealed that CL interacted with the ligand through weak hydrogen bonds, and then approached the Ti center. After being attacked by isopropyl oxide, the carbonyl group of CL bonded to the Ti center. After the rearrangement and ring opening of CL ring, CL was converted to poly-ε-caprolactone.
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•Ti compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized.•LA and CL polymerizations were investigated.•MeLPh-TiOPr2 exhibited the highest catalytic activity. |
| doi_str_mv | 10.1016/j.polymer.2020.122860 |
| format | Article |
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[Display omitted]
•Ti compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized.•LA and CL polymerizations were investigated.•MeLPh-TiOPr2 exhibited the highest catalytic activity.</description><identifier>ISSN: 0032-3861</identifier><identifier>EISSN: 1873-2291</identifier><identifier>DOI: 10.1016/j.polymer.2020.122860</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Bonding strength ; Carbonyl compounds ; Carbonyl groups ; Carbonyls ; Catalysts ; Catalytic activity ; Chemical synthesis ; Conversion ; Density functional theory ; Hydrogen bonding ; Hydrogen bonds ; L-lactide ; Ligands ; Polycaprolactone ; Polymerization ; Pyridines ; Ring opening polymerization ; Titanium ; Titanium complex ; Titanium compounds ; ε-Caprolactone</subject><ispartof>Polymer (Guilford), 2020-09, Vol.204, p.122860, Article 122860</ispartof><rights>2020 Elsevier Ltd</rights><rights>Copyright Elsevier BV Sep 9, 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-47895bd0f6dc586ade1d6eafbaa0f66bd89474c6d78bdf10044a7b64cbf2f8e73</citedby><cites>FETCH-LOGICAL-c337t-47895bd0f6dc586ade1d6eafbaa0f66bd89474c6d78bdf10044a7b64cbf2f8e73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S003238612030687X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Lai, Feng-Jie</creatorcontrib><creatorcontrib>Huang, Tsai-Wen</creatorcontrib><creatorcontrib>Chang, Yu-Lun</creatorcontrib><creatorcontrib>Chang, Heng-Yi</creatorcontrib><creatorcontrib>Lu, Wei-Yi</creatorcontrib><creatorcontrib>Ding, Shangwu</creatorcontrib><creatorcontrib>Chen, Hsuan-Ying</creatorcontrib><creatorcontrib>Chiu, Chien-Chih</creatorcontrib><creatorcontrib>Wu, Kuo-Hui</creatorcontrib><title>Titanium complexes bearing 2,6-Bis(o-hydroxyalkyl)pyridine ligands in the ring-opening polymerization of L-Lactide and ε-caprolactone</title><title>Polymer (Guilford)</title><description>A series of titanium (Ti) compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized and investigated as catalysts for the ring-opening polymerization of ε-caprolactone (CL) and L-lactide (LA). The Ti complexes with electron-withdrawing groups in pyridine rings or steric bulky groups in hydroxymethyl groups reduced the catalytic activity in CL and LA polymerizations, and MeLPh-TiOPr2 exhibited the highest catalytic activity ([CL] = 0.5 M, [CL]:[Cat] = 100:8, 60 °C, 7.5 h, conversion = 93%; [LA] = 0.5 M, [LA]:[Cat] = 100:8, 60 °C, 3.5 h, conversion = 98%). The density functional theory calculation results revealed that CL interacted with the ligand through weak hydrogen bonds, and then approached the Ti center. After being attacked by isopropyl oxide, the carbonyl group of CL bonded to the Ti center. After the rearrangement and ring opening of CL ring, CL was converted to poly-ε-caprolactone.
[Display omitted]
•Ti compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized.•LA and CL polymerizations were investigated.•MeLPh-TiOPr2 exhibited the highest catalytic activity.</description><subject>Bonding strength</subject><subject>Carbonyl compounds</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Catalysts</subject><subject>Catalytic activity</subject><subject>Chemical synthesis</subject><subject>Conversion</subject><subject>Density functional theory</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>L-lactide</subject><subject>Ligands</subject><subject>Polycaprolactone</subject><subject>Polymerization</subject><subject>Pyridines</subject><subject>Ring opening polymerization</subject><subject>Titanium</subject><subject>Titanium complex</subject><subject>Titanium compounds</subject><subject>ε-Caprolactone</subject><issn>0032-3861</issn><issn>1873-2291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkM1qGzEUhUVJoU7aRygIskkgciWNrJFXITFJWxjoJl0LjXQnkTOWJtK4ePoAfaO8Rp6pMvY-qwvnnu_-HIS-MjpnlMlv6_kQ-2kDac4pLxrnStIPaMZUXRHOl-wEzSitOKmUZJ_Qac5rSilfcDFD_x78aILfbrCNm6GHHWTcgkk-PGJ-JcmtzxeRPE0uxd1k-uepvxym5J0PgHv_aILL2Ac8PgHeMyQOEPbs8SL_14w-Bhw73JDG2NE7wAXCb6_EmiHFvmgxwGf0sTN9hi_HeoZ-3989rH6Q5tf3n6ubhtiqqkciarVctI520tmFksYBcxJM1xpTNNk6tRS1sNLVqnUdo1QIU7dS2LbjnYK6OkPnh7ll9csW8qjXcZtCWam5EIWupKqKa3Fw2RRzTtDpIfmNSZNmVO8j12t9fFDvI9eHyAt3feCgvPDHl262HoIF5xPYUbvo35nwH8i_kN8</recordid><startdate>20200909</startdate><enddate>20200909</enddate><creator>Lai, Feng-Jie</creator><creator>Huang, Tsai-Wen</creator><creator>Chang, Yu-Lun</creator><creator>Chang, Heng-Yi</creator><creator>Lu, Wei-Yi</creator><creator>Ding, Shangwu</creator><creator>Chen, Hsuan-Ying</creator><creator>Chiu, Chien-Chih</creator><creator>Wu, Kuo-Hui</creator><general>Elsevier Ltd</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7T7</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope></search><sort><creationdate>20200909</creationdate><title>Titanium complexes bearing 2,6-Bis(o-hydroxyalkyl)pyridine ligands in the ring-opening polymerization of L-Lactide and ε-caprolactone</title><author>Lai, Feng-Jie ; Huang, Tsai-Wen ; Chang, Yu-Lun ; Chang, Heng-Yi ; Lu, Wei-Yi ; Ding, Shangwu ; Chen, Hsuan-Ying ; Chiu, Chien-Chih ; Wu, Kuo-Hui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-47895bd0f6dc586ade1d6eafbaa0f66bd89474c6d78bdf10044a7b64cbf2f8e73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Bonding strength</topic><topic>Carbonyl compounds</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Catalysts</topic><topic>Catalytic activity</topic><topic>Chemical synthesis</topic><topic>Conversion</topic><topic>Density functional theory</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>L-lactide</topic><topic>Ligands</topic><topic>Polycaprolactone</topic><topic>Polymerization</topic><topic>Pyridines</topic><topic>Ring opening polymerization</topic><topic>Titanium</topic><topic>Titanium complex</topic><topic>Titanium compounds</topic><topic>ε-Caprolactone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lai, Feng-Jie</creatorcontrib><creatorcontrib>Huang, Tsai-Wen</creatorcontrib><creatorcontrib>Chang, Yu-Lun</creatorcontrib><creatorcontrib>Chang, Heng-Yi</creatorcontrib><creatorcontrib>Lu, Wei-Yi</creatorcontrib><creatorcontrib>Ding, Shangwu</creatorcontrib><creatorcontrib>Chen, Hsuan-Ying</creatorcontrib><creatorcontrib>Chiu, Chien-Chih</creatorcontrib><creatorcontrib>Wu, Kuo-Hui</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Polymer (Guilford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lai, Feng-Jie</au><au>Huang, Tsai-Wen</au><au>Chang, Yu-Lun</au><au>Chang, Heng-Yi</au><au>Lu, Wei-Yi</au><au>Ding, Shangwu</au><au>Chen, Hsuan-Ying</au><au>Chiu, Chien-Chih</au><au>Wu, Kuo-Hui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Titanium complexes bearing 2,6-Bis(o-hydroxyalkyl)pyridine ligands in the ring-opening polymerization of L-Lactide and ε-caprolactone</atitle><jtitle>Polymer (Guilford)</jtitle><date>2020-09-09</date><risdate>2020</risdate><volume>204</volume><spage>122860</spage><pages>122860-</pages><artnum>122860</artnum><issn>0032-3861</issn><eissn>1873-2291</eissn><abstract>A series of titanium (Ti) compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized and investigated as catalysts for the ring-opening polymerization of ε-caprolactone (CL) and L-lactide (LA). The Ti complexes with electron-withdrawing groups in pyridine rings or steric bulky groups in hydroxymethyl groups reduced the catalytic activity in CL and LA polymerizations, and MeLPh-TiOPr2 exhibited the highest catalytic activity ([CL] = 0.5 M, [CL]:[Cat] = 100:8, 60 °C, 7.5 h, conversion = 93%; [LA] = 0.5 M, [LA]:[Cat] = 100:8, 60 °C, 3.5 h, conversion = 98%). The density functional theory calculation results revealed that CL interacted with the ligand through weak hydrogen bonds, and then approached the Ti center. After being attacked by isopropyl oxide, the carbonyl group of CL bonded to the Ti center. After the rearrangement and ring opening of CL ring, CL was converted to poly-ε-caprolactone.
[Display omitted]
•Ti compounds bearing 2,6-bis(o-hydroxyalkyl)pyridine ligands were synthesized.•LA and CL polymerizations were investigated.•MeLPh-TiOPr2 exhibited the highest catalytic activity.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.polymer.2020.122860</doi></addata></record> |
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| ispartof | Polymer (Guilford), 2020-09, Vol.204, p.122860, Article 122860 |
| issn | 0032-3861 1873-2291 |
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| subjects | Bonding strength Carbonyl compounds Carbonyl groups Carbonyls Catalysts Catalytic activity Chemical synthesis Conversion Density functional theory Hydrogen bonding Hydrogen bonds L-lactide Ligands Polycaprolactone Polymerization Pyridines Ring opening polymerization Titanium Titanium complex Titanium compounds ε-Caprolactone |
| title | Titanium complexes bearing 2,6-Bis(o-hydroxyalkyl)pyridine ligands in the ring-opening polymerization of L-Lactide and ε-caprolactone |
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