Grafting (S)-2-Phenylpropionic Acid on Coordinatively Unsaturated Metal Centers of MIL-101(Al) Metal-Organic Frameworks for Improved Enantioseparation
Chiral metal-organic frameworks (cMOFs) are emerging chiral stationary phases for enantioseparation owing to their porosity and designability. However, a great number of cMOF materials show poor separation performance for chiral drugs in high-performance liquid chromatography (HPLC). The possible re...
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| description | Chiral metal-organic frameworks (cMOFs) are emerging chiral stationary phases for enantioseparation owing to their porosity and designability. However, a great number of cMOF materials show poor separation performance for chiral drugs in high-performance liquid chromatography (HPLC). The possible reasons might be the irregular shapes of MOFs and the low grafting degree of chiral ligands. Herein, MIL-101-Ppa@SiO
was synthesized by a simple coordination post-synthetic modification method using (S)-(+)-2-Phenylpropionic acid and applied as the chiral stationary phase to separate chiral compounds by HPLC. NH
-MIL-101-Ppa@SiO
prepared via covalent post-synthetic modification was used for comparison. The results showed that the chiral ligand density of MIL-101-Ppa@SiO
was higher than that of NH
-MIL-101-Ppa@SiO
, and the MIL-101-Ppa@SiO
column exhibited better chiral separation performance and structural stability. The binding affinities between MIL-101-Ppa@SiO
and chiral compounds were simulated to prove the mechanism of the molecular interactions during HPLC. These results revealed that cMOFs prepared by coordination post-synthetic modification could increase the grafting degree and enhance the separation performance. This method can provide ideas for the synthesis of cMOFs. |
| doi_str_mv | 10.3390/ma15238456 |
| format | Article |
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was synthesized by a simple coordination post-synthetic modification method using (S)-(+)-2-Phenylpropionic acid and applied as the chiral stationary phase to separate chiral compounds by HPLC. NH
-MIL-101-Ppa@SiO
prepared via covalent post-synthetic modification was used for comparison. The results showed that the chiral ligand density of MIL-101-Ppa@SiO
was higher than that of NH
-MIL-101-Ppa@SiO
, and the MIL-101-Ppa@SiO
column exhibited better chiral separation performance and structural stability. The binding affinities between MIL-101-Ppa@SiO
and chiral compounds were simulated to prove the mechanism of the molecular interactions during HPLC. These results revealed that cMOFs prepared by coordination post-synthetic modification could increase the grafting degree and enhance the separation performance. This method can provide ideas for the synthesis of cMOFs.</description><identifier>ISSN: 1996-1944</identifier><identifier>EISSN: 1996-1944</identifier><identifier>DOI: 10.3390/ma15238456</identifier><identifier>PMID: 36499951</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acids ; Aluminum ; Chromatography ; Coordination ; Ethanol ; Grafting ; High performance liquid chromatography ; Ligands ; Metal-organic frameworks ; Molecular interactions ; Porous materials ; Separation ; Severe acute respiratory syndrome coronavirus 2 ; Silicon dioxide ; Structural stability</subject><ispartof>Materials, 2022-11, Vol.15 (23), p.8456</ispartof><rights>2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2022 by the authors. 2022</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c406t-7f4a25bdd450952a0da771487d108e240c8343ed822e99936f2f5669789718733</citedby><cites>FETCH-LOGICAL-c406t-7f4a25bdd450952a0da771487d108e240c8343ed822e99936f2f5669789718733</cites><orcidid>0000-0001-5054-0855 ; 0000-0001-6131-9515 ; 0000-0002-2410-7078</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9740726/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9740726/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27903,27904,53769,53771</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36499951$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhao, Rui</creatorcontrib><creatorcontrib>Bai, Xueyan</creatorcontrib><creatorcontrib>Yang, Wenhui</creatorcontrib><creatorcontrib>Fan, Kun</creatorcontrib><creatorcontrib>Zhang, Haiyang</creatorcontrib><title>Grafting (S)-2-Phenylpropionic Acid on Coordinatively Unsaturated Metal Centers of MIL-101(Al) Metal-Organic Frameworks for Improved Enantioseparation</title><title>Materials</title><addtitle>Materials (Basel)</addtitle><description>Chiral metal-organic frameworks (cMOFs) are emerging chiral stationary phases for enantioseparation owing to their porosity and designability. However, a great number of cMOF materials show poor separation performance for chiral drugs in high-performance liquid chromatography (HPLC). The possible reasons might be the irregular shapes of MOFs and the low grafting degree of chiral ligands. Herein, MIL-101-Ppa@SiO
was synthesized by a simple coordination post-synthetic modification method using (S)-(+)-2-Phenylpropionic acid and applied as the chiral stationary phase to separate chiral compounds by HPLC. NH
-MIL-101-Ppa@SiO
prepared via covalent post-synthetic modification was used for comparison. The results showed that the chiral ligand density of MIL-101-Ppa@SiO
was higher than that of NH
-MIL-101-Ppa@SiO
, and the MIL-101-Ppa@SiO
column exhibited better chiral separation performance and structural stability. The binding affinities between MIL-101-Ppa@SiO
and chiral compounds were simulated to prove the mechanism of the molecular interactions during HPLC. These results revealed that cMOFs prepared by coordination post-synthetic modification could increase the grafting degree and enhance the separation performance. This method can provide ideas for the synthesis of cMOFs.</description><subject>Acids</subject><subject>Aluminum</subject><subject>Chromatography</subject><subject>Coordination</subject><subject>Ethanol</subject><subject>Grafting</subject><subject>High performance liquid chromatography</subject><subject>Ligands</subject><subject>Metal-organic frameworks</subject><subject>Molecular interactions</subject><subject>Porous materials</subject><subject>Separation</subject><subject>Severe acute respiratory syndrome coronavirus 2</subject><subject>Silicon dioxide</subject><subject>Structural stability</subject><issn>1996-1944</issn><issn>1996-1944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNpdkd9KHDEUh4O0qFhvfIAS6M1amDZ_J8lNYVnULqxYqF6HOJNZY2eSaZJZ2Rfp8zbLWmubmxM4H985hx8AZxh9olShz4PBnFDJeH0AjrFSdYUVY29e_Y_AaUqPqDxKsSTqEBzRmimlOD4Gv66i6bLzazj7fl6R6tuD9dt-jGF0wbsGzhvXwuDhIoTYOm-y29h-C-98MnmKJtsWXttseriwPtuYYOjg9XJVYYRn8_5836xu4trsbJfRDPYpxB8JdiHC5VAGbYriwhufXUh2NMVZJr8DbzvTJ3v6XE_A3eXF7eJrtbq5Wi7mq6phqM6V6Jgh_L5tGUeKE4NaIwRmUrQYSUsYaiRl1LaSEFsOpnVHOl7XSkglsBSUnoAve-843Q-2bcoR0fR6jG4wcauDcfrfjncPeh02WgmGBKmLYPYsiOHnZFPWg0uN7XvjbZiSJoJTigSmvKAf_kMfwxR9Oa9QTHJeC7mjPu6pJoaUou1elsFI7xLXfxMv8PvX67-gf_KlvwGFHKX0</recordid><startdate>20221127</startdate><enddate>20221127</enddate><creator>Zhao, Rui</creator><creator>Bai, Xueyan</creator><creator>Yang, Wenhui</creator><creator>Fan, Kun</creator><creator>Zhang, Haiyang</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>COVID</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-5054-0855</orcidid><orcidid>https://orcid.org/0000-0001-6131-9515</orcidid><orcidid>https://orcid.org/0000-0002-2410-7078</orcidid></search><sort><creationdate>20221127</creationdate><title>Grafting (S)-2-Phenylpropionic Acid on Coordinatively Unsaturated Metal Centers of MIL-101(Al) Metal-Organic Frameworks for Improved Enantioseparation</title><author>Zhao, Rui ; Bai, Xueyan ; Yang, Wenhui ; Fan, Kun ; Zhang, Haiyang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c406t-7f4a25bdd450952a0da771487d108e240c8343ed822e99936f2f5669789718733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Acids</topic><topic>Aluminum</topic><topic>Chromatography</topic><topic>Coordination</topic><topic>Ethanol</topic><topic>Grafting</topic><topic>High performance liquid chromatography</topic><topic>Ligands</topic><topic>Metal-organic frameworks</topic><topic>Molecular interactions</topic><topic>Porous materials</topic><topic>Separation</topic><topic>Severe acute respiratory syndrome coronavirus 2</topic><topic>Silicon dioxide</topic><topic>Structural stability</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhao, Rui</creatorcontrib><creatorcontrib>Bai, Xueyan</creatorcontrib><creatorcontrib>Yang, Wenhui</creatorcontrib><creatorcontrib>Fan, Kun</creatorcontrib><creatorcontrib>Zhang, Haiyang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Databases</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>Coronavirus Research Database</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials science collection</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhao, Rui</au><au>Bai, Xueyan</au><au>Yang, Wenhui</au><au>Fan, Kun</au><au>Zhang, Haiyang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Grafting (S)-2-Phenylpropionic Acid on Coordinatively Unsaturated Metal Centers of MIL-101(Al) Metal-Organic Frameworks for Improved Enantioseparation</atitle><jtitle>Materials</jtitle><addtitle>Materials (Basel)</addtitle><date>2022-11-27</date><risdate>2022</risdate><volume>15</volume><issue>23</issue><spage>8456</spage><pages>8456-</pages><issn>1996-1944</issn><eissn>1996-1944</eissn><abstract>Chiral metal-organic frameworks (cMOFs) are emerging chiral stationary phases for enantioseparation owing to their porosity and designability. However, a great number of cMOF materials show poor separation performance for chiral drugs in high-performance liquid chromatography (HPLC). The possible reasons might be the irregular shapes of MOFs and the low grafting degree of chiral ligands. Herein, MIL-101-Ppa@SiO
was synthesized by a simple coordination post-synthetic modification method using (S)-(+)-2-Phenylpropionic acid and applied as the chiral stationary phase to separate chiral compounds by HPLC. NH
-MIL-101-Ppa@SiO
prepared via covalent post-synthetic modification was used for comparison. The results showed that the chiral ligand density of MIL-101-Ppa@SiO
was higher than that of NH
-MIL-101-Ppa@SiO
, and the MIL-101-Ppa@SiO
column exhibited better chiral separation performance and structural stability. The binding affinities between MIL-101-Ppa@SiO
and chiral compounds were simulated to prove the mechanism of the molecular interactions during HPLC. These results revealed that cMOFs prepared by coordination post-synthetic modification could increase the grafting degree and enhance the separation performance. This method can provide ideas for the synthesis of cMOFs.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>36499951</pmid><doi>10.3390/ma15238456</doi><orcidid>https://orcid.org/0000-0001-5054-0855</orcidid><orcidid>https://orcid.org/0000-0001-6131-9515</orcidid><orcidid>https://orcid.org/0000-0002-2410-7078</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Materials, 2022-11, Vol.15 (23), p.8456 |
| issn | 1996-1944 1996-1944 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9740726 |
| source | PubMed Central Open Access; MDPI - Multidisciplinary Digital Publishing Institute; PubMed Central; Free Full-Text Journals in Chemistry; EZB Electronic Journals Library |
| subjects | Acids Aluminum Chromatography Coordination Ethanol Grafting High performance liquid chromatography Ligands Metal-organic frameworks Molecular interactions Porous materials Separation Severe acute respiratory syndrome coronavirus 2 Silicon dioxide Structural stability |
| title | Grafting (S)-2-Phenylpropionic Acid on Coordinatively Unsaturated Metal Centers of MIL-101(Al) Metal-Organic Frameworks for Improved Enantioseparation |
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