A unique quinolineboronic acid-based supramolecular structure that relies on double intermolecular B–N bonds for self-assembly in solid state and in solution
The boronic acid functional group plays very important roles in sugar recognition, catalysis, organic synthesis, and supramolecular assembly. Therefore, understanding the unique properties of this functional group is very important. 8-Quinolineboronic acid (8-QBA) is found to be capable of self-asse...
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Veröffentlicht in: | Tetrahedron 2007-04, Vol.63 (16), p.3287-3292 |
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creator | Zhang, Yanling Li, Minyong Chandrasekaran, Sekar Gao, Xingming Fang, Xikui Lee, Hsiau-Wei Hardcastle, Kenneth Yang, Jenny Wang, Binghe |
description | The boronic acid functional group plays very important roles in sugar recognition, catalysis, organic synthesis, and supramolecular assembly. Therefore, understanding the unique properties of this functional group is very important. 8-Quinolineboronic acid (8-QBA) is found to be capable of self-assembling in solid state through a unique intermolecular B–N bond mechanism reinforced by intermolecular boronic anhydride formation, π–π stacking, and hydrogen bond formation. NMR NOE and diffusion studies indicate that intermolecular B–N interaction also exists in solution with 8-QBA. In contrast, a positional isomer of 8-QBA, 5-quinolineboronic acid (5-QBA) showed very different behaviors in crystal packing and in solution and therefore different supramolecular network. Understanding the structural features of this unique 8-QBA assembly could be very helpful for the future design of new sugar sensors, molecular catalysts, and supramolecular assemblies.
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doi_str_mv | 10.1016/j.tet.2007.02.042 |
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[Display omitted]</description><subject>Crystal structure</subject><subject>NMR</subject><subject>Quinolineboronic acid</subject><subject>Self-assembly</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1DAURi0EokPhAdggL9kkXDuOk4hVqYBWqmADa8uxb4RHiT31D1J3vAMPwLvxJHg0I3XHxpas831X14eQ1wxaBky-27cZc8sBhhZ4C4I_ITsmpGh6weRTsgMQ0AjgcEFepLQHAMZ495xcsFEcuX5H_lzR4t19QXpfnA-r8ziHGLwzVBtnm1kntDSVQ9RbWNGUVUeaciwml4g0_9CZRlwdJho8taHMK1LnM8ZH_MPfX7-_0Dl4m-gSahzXpdEp4TavDxWmqc6tQ7LOSLW356eSXfAvybNFrwlfne9L8v3Tx2_XN83d18-311d3jekmmRvNbA_L1I8gByMsg6lnduJisssgeS86Lg2b5bwYabEbYZq6oR8mqEc_4zR2l-TtqfcQQ_2NlNXmksF11R5DSYqNXS8kFx1UlJ1QE0NKERd1iG7T8UExUEcvaq-qF3X0ooCr6qVm3pzry7yhfUycRVTg_QnAuuRPh1El49AbtC6iycoG95_6f1YQoW0</recordid><startdate>20070416</startdate><enddate>20070416</enddate><creator>Zhang, Yanling</creator><creator>Li, Minyong</creator><creator>Chandrasekaran, Sekar</creator><creator>Gao, Xingming</creator><creator>Fang, Xikui</creator><creator>Lee, Hsiau-Wei</creator><creator>Hardcastle, Kenneth</creator><creator>Yang, Jenny</creator><creator>Wang, Binghe</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20070416</creationdate><title>A unique quinolineboronic acid-based supramolecular structure that relies on double intermolecular B–N bonds for self-assembly in solid state and in solution</title><author>Zhang, Yanling ; Li, Minyong ; Chandrasekaran, Sekar ; Gao, Xingming ; Fang, Xikui ; Lee, Hsiau-Wei ; Hardcastle, Kenneth ; Yang, Jenny ; Wang, Binghe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-a1d50f958067c4d10951d9249df76254326c1b6bfc6de380993757907575be983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Crystal structure</topic><topic>NMR</topic><topic>Quinolineboronic acid</topic><topic>Self-assembly</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Yanling</creatorcontrib><creatorcontrib>Li, Minyong</creatorcontrib><creatorcontrib>Chandrasekaran, Sekar</creatorcontrib><creatorcontrib>Gao, Xingming</creatorcontrib><creatorcontrib>Fang, Xikui</creatorcontrib><creatorcontrib>Lee, Hsiau-Wei</creatorcontrib><creatorcontrib>Hardcastle, Kenneth</creatorcontrib><creatorcontrib>Yang, Jenny</creatorcontrib><creatorcontrib>Wang, Binghe</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Yanling</au><au>Li, Minyong</au><au>Chandrasekaran, Sekar</au><au>Gao, Xingming</au><au>Fang, Xikui</au><au>Lee, Hsiau-Wei</au><au>Hardcastle, Kenneth</au><au>Yang, Jenny</au><au>Wang, Binghe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A unique quinolineboronic acid-based supramolecular structure that relies on double intermolecular B–N bonds for self-assembly in solid state and in solution</atitle><jtitle>Tetrahedron</jtitle><addtitle>Tetrahedron</addtitle><date>2007-04-16</date><risdate>2007</risdate><volume>63</volume><issue>16</issue><spage>3287</spage><epage>3292</epage><pages>3287-3292</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>The boronic acid functional group plays very important roles in sugar recognition, catalysis, organic synthesis, and supramolecular assembly. Therefore, understanding the unique properties of this functional group is very important. 8-Quinolineboronic acid (8-QBA) is found to be capable of self-assembling in solid state through a unique intermolecular B–N bond mechanism reinforced by intermolecular boronic anhydride formation, π–π stacking, and hydrogen bond formation. NMR NOE and diffusion studies indicate that intermolecular B–N interaction also exists in solution with 8-QBA. In contrast, a positional isomer of 8-QBA, 5-quinolineboronic acid (5-QBA) showed very different behaviors in crystal packing and in solution and therefore different supramolecular network. Understanding the structural features of this unique 8-QBA assembly could be very helpful for the future design of new sugar sensors, molecular catalysts, and supramolecular assemblies.
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subjects | Crystal structure NMR Quinolineboronic acid Self-assembly |
title | A unique quinolineboronic acid-based supramolecular structure that relies on double intermolecular B–N bonds for self-assembly in solid state and in solution |
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