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A conformationally adaptive macrocycle: conformational complexity and host-guest chemistry of zorb[4]arene
Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present...
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| Published in: | Beilstein journal of organic chemistry 2018-06, Vol.14 (1), p.1570-1577 |
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| Main Authors: | , , , , , |
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| container_title | Beilstein journal of organic chemistry |
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| creator | Yang, Liu-Pan Lu, Song-Bo Valkonen, Arto Pan, Fangfang Rissanen, Kari Jiang, Wei |
| description | Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host-guest chemistry of a conformationally adaptive macrocycle, namely per-
-ethoxyzorb[4]arene (
). Similar to per-
-ethoxyoxatub[4]arene,
is capable of accommodating a wide range of organic cations. However,
does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship,
follows a parabolic free-energy relationship. This is explained by invoking the influence of secondary C-H···O hydrogen bonds on the primary cation···π interactions based on the information obtained from four representative crystal structures. In addition, heat capacity changes (Δ
) and enthalpy-entropy compensation phenomena both indicate that solvent reorganization is also involved during the binding. This research further deepens our understanding on the binding behavior of
and lays the basis for the construction of stimuli-responsive materials with
as a major component. |
| doi_str_mv | 10.3762/bjoc.14.134 |
| format | article |
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-ethoxyzorb[4]arene (
). Similar to per-
-ethoxyoxatub[4]arene,
is capable of accommodating a wide range of organic cations. However,
does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship,
follows a parabolic free-energy relationship. This is explained by invoking the influence of secondary C-H···O hydrogen bonds on the primary cation···π interactions based on the information obtained from four representative crystal structures. In addition, heat capacity changes (Δ
) and enthalpy-entropy compensation phenomena both indicate that solvent reorganization is also involved during the binding. This research further deepens our understanding on the binding behavior of
and lays the basis for the construction of stimuli-responsive materials with
as a major component.</description><identifier>ISSN: 1860-5397</identifier><identifier>ISSN: 2195-951X</identifier><identifier>EISSN: 1860-5397</identifier><identifier>DOI: 10.3762/bjoc.14.134</identifier><identifier>PMID: 30013684</identifier><language>eng</language><publisher>Germany: Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</publisher><subject>Allosteric properties ; Cations ; Chemistry ; conformations ; Entropy ; Free energy ; Full Research Paper ; Heat ; host–guest chemistry ; Hydrogen bonding ; macrocycles ; Signal transduction ; Solvents ; supramolecular chemistry ; zorbarene</subject><ispartof>Beilstein journal of organic chemistry, 2018-06, Vol.14 (1), p.1570-1577</ispartof><rights>Copyright © 2018, Yang et al.; licensee Beilstein-Institut. This work is published under http://creativecommons.org/licenses/by/4.0 (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Copyright © 2018, Yang et al. 2018 Yang et al.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c475t-ba7bdbed3183ba3942fa4dedb2b7c56e06f2cf6808e1b8999278a8637d1531a73</citedby><cites>FETCH-LOGICAL-c475t-ba7bdbed3183ba3942fa4dedb2b7c56e06f2cf6808e1b8999278a8637d1531a73</cites><orcidid>0000-0002-7282-8419 ; 0000-0003-2806-3807</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2080462365/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2080462365?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,25731,27901,27902,36989,36990,44566,53766,53768,74869</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30013684$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Liu-Pan</creatorcontrib><creatorcontrib>Lu, Song-Bo</creatorcontrib><creatorcontrib>Valkonen, Arto</creatorcontrib><creatorcontrib>Pan, Fangfang</creatorcontrib><creatorcontrib>Rissanen, Kari</creatorcontrib><creatorcontrib>Jiang, Wei</creatorcontrib><title>A conformationally adaptive macrocycle: conformational complexity and host-guest chemistry of zorb[4]arene</title><title>Beilstein journal of organic chemistry</title><addtitle>Beilstein J Org Chem</addtitle><description>Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host-guest chemistry of a conformationally adaptive macrocycle, namely per-
-ethoxyzorb[4]arene (
). Similar to per-
-ethoxyoxatub[4]arene,
is capable of accommodating a wide range of organic cations. However,
does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship,
follows a parabolic free-energy relationship. This is explained by invoking the influence of secondary C-H···O hydrogen bonds on the primary cation···π interactions based on the information obtained from four representative crystal structures. In addition, heat capacity changes (Δ
) and enthalpy-entropy compensation phenomena both indicate that solvent reorganization is also involved during the binding. This research further deepens our understanding on the binding behavior of
and lays the basis for the construction of stimuli-responsive materials with
as a major component.</description><subject>Allosteric properties</subject><subject>Cations</subject><subject>Chemistry</subject><subject>conformations</subject><subject>Entropy</subject><subject>Free energy</subject><subject>Full Research Paper</subject><subject>Heat</subject><subject>host–guest chemistry</subject><subject>Hydrogen bonding</subject><subject>macrocycles</subject><subject>Signal transduction</subject><subject>Solvents</subject><subject>supramolecular chemistry</subject><subject>zorbarene</subject><issn>1860-5397</issn><issn>2195-951X</issn><issn>1860-5397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNpdkstrFTEUh4NYbK2u3MuAG0HmmncyLoRS1BYKbnQlEk4ec-8MM5NrMrf09q83462l7Sqvj49zTn4IvSF4xZSkH20f3YrwFWH8GTohWuJasEY9f7A_Ri9z7jHmWGL5Ah0zjAmTmp-g_qxycWpjGmHu4gTDsK_Aw3burkM1gkvR7d0QPj2hynHcDuGmmws--WoT81yvdyHPlduEsctz2lexrW5jsr_4b0hhCq_QUQtDDq_v1lP08-uXH-cX9dX3b5fnZ1e140rMtQVlvQ2eEc0ssIbTFrgP3lKrnJABy5a6VmqsA7G6aRqqNGjJlCeCEVDsFF0evD5Cb7apGyHtTYTO_LuIaW0gzV3pylBJGKNUtIpajpWFQLACJbigjnrWFNfng2u7s2PwLkxzguGR9PHL1G3MOl4biZnCZBG8vxOk-GeZjynDcWEYYApxlw3FigjFqeAFffcE7eMulWEvlMZcUiZFoT4cqPI1OafQ3hdDsFnyYJY8GMJNyUOh3z6s_579HwD2F1gOsuw</recordid><startdate>20180627</startdate><enddate>20180627</enddate><creator>Yang, Liu-Pan</creator><creator>Lu, Song-Bo</creator><creator>Valkonen, Arto</creator><creator>Pan, Fangfang</creator><creator>Rissanen, Kari</creator><creator>Jiang, Wei</creator><general>Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</general><general>Beilstein-Institut</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BFMQW</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>LK8</scope><scope>M2P</scope><scope>M7P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-7282-8419</orcidid><orcidid>https://orcid.org/0000-0003-2806-3807</orcidid></search><sort><creationdate>20180627</creationdate><title>A conformationally adaptive macrocycle: conformational complexity and host-guest chemistry of zorb[4]arene</title><author>Yang, Liu-Pan ; 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However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host-guest chemistry of a conformationally adaptive macrocycle, namely per-
-ethoxyzorb[4]arene (
). Similar to per-
-ethoxyoxatub[4]arene,
is capable of accommodating a wide range of organic cations. However,
does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship,
follows a parabolic free-energy relationship. This is explained by invoking the influence of secondary C-H···O hydrogen bonds on the primary cation···π interactions based on the information obtained from four representative crystal structures. In addition, heat capacity changes (Δ
) and enthalpy-entropy compensation phenomena both indicate that solvent reorganization is also involved during the binding. This research further deepens our understanding on the binding behavior of
and lays the basis for the construction of stimuli-responsive materials with
as a major component.</abstract><cop>Germany</cop><pub>Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</pub><pmid>30013684</pmid><doi>10.3762/bjoc.14.134</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-7282-8419</orcidid><orcidid>https://orcid.org/0000-0003-2806-3807</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Beilstein journal of organic chemistry, 2018-06, Vol.14 (1), p.1570-1577 |
| issn | 1860-5397 2195-951X 1860-5397 |
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| subjects | Allosteric properties Cations Chemistry conformations Entropy Free energy Full Research Paper Heat host–guest chemistry Hydrogen bonding macrocycles Signal transduction Solvents supramolecular chemistry zorbarene |
| title | A conformationally adaptive macrocycle: conformational complexity and host-guest chemistry of zorb[4]arene |
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