{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,13]],"date-time":"2026-01-13T01:29:13Z","timestamp":1768267753164,"version":"3.49.0"},"reference-count":55,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2022,12,28]],"date-time":"2022-12-28T00:00:00Z","timestamp":1672185600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/N509711\/1"],"award-info":[{"award-number":["EP\/N509711\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2023,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A halogen bonding (XB) heteroditopic receptor, consisting of a 1,3\u2010bis\u2010iodo\u2010triazole benzene XB anion binding site covalently appended via a flexible methylene group with two benzo\u201015\u2010crown\u20105 (B15C5) cation binding moieties, and its hydrogen bonding receptor analogue, are used to delineate the mechanisms of cooperativity for alkali metal halide ion\u2010pair recognition. Extensive cation, anion and ion\u2010pair <jats:sup>1<\/jats:sup>H NMR titration investigations demonstrate the combination of allosteric pre\u2010organisation, via 1\u2009:\u20091 stoichiometric intramolecular potassium and rubidium metal cation bis\u2010B15C5 sandwich complexation, in concert with favourable electrostatics and XB potency, results in a remarkable enhancement of halide anion binding affinity by a factor of at least 700. By contrast, a notably diminished halide anion affinity enhancement factor of just 15 is observed with the corresponding 1\u2009:\u20091 stoichiometric sodium cation complexed receptor system, where the smaller sized cation singly occupies one B15C5 unit and only an electrostatic contribution to cooperativity is possible. These observations serve to illustrate that allosteric pre\u2010organisation capability, electrostatic attraction and XB mediated anion recognition are important strategic design features to incorporate in future high\u2010fidelity heteroditopic ion\u2010pair receptor development.<\/jats:p>","DOI":"10.1002\/asia.202201170","type":"journal-article","created":{"date-parts":[[2022,12,14]],"date-time":"2022-12-14T15:27:56Z","timestamp":1671031676000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Allosteric and Electrostatic Cooperativity in a Heteroditopic Halogen Bonding Receptor System"],"prefix":"10.1002","volume":"18","author":[{"given":"Andrew J.","family":"Taylor","sequence":"first","affiliation":[{"name":"Chemistry Research Laboratory Department of Chemistry University of Oxford  12 Mansfield Road Oxford OX1 3TA UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrew","family":"Docker","sequence":"additional","affiliation":[{"name":"Chemistry Research Laboratory Department of Chemistry University of Oxford  12 Mansfield Road Oxford OX1 3TA UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0810-9716","authenticated-orcid":false,"given":"Paul D.","family":"Beer","sequence":"additional","affiliation":[{"name":"Chemistry Research Laboratory Department of Chemistry University of Oxford  12 Mansfield Road Oxford OX1 3TA UK"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,12,28]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"crossref","first-page":"3784","DOI":"10.1039\/c002694h","volume":"39","author":"Kim S. K.","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"e_1_2_7_2_1","doi-asserted-by":"crossref","first-page":"1824","DOI":"10.1002\/cplu.202000484","volume":"85","author":"McConnell A. J.","year":"2020","journal-title":"ChemPlusChem"},{"key":"e_1_2_7_3_1","first-page":"259","volume-title":"Anion Receptor Chemistry","author":"Cho J. L. S. P. A. G. a. W.-S.","year":"2006"},{"key":"e_1_2_7_4_1","doi-asserted-by":"crossref","first-page":"14778","DOI":"10.1021\/jacs.2c05333","volume":"144","author":"Docker A.","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_5_1","doi-asserted-by":"crossref","first-page":"7488","DOI":"10.1002\/anie.200902490","volume":"48","author":"Hunter C. A.","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_5_2","doi-asserted-by":"crossref","first-page":"7624","DOI":"10.1002\/ange.200902490","volume":"121","year":"2009","journal-title":"Angew. Chem."},{"key":"e_1_2_7_6_1","doi-asserted-by":"crossref","first-page":"8296","DOI":"10.1002\/chem.200900342","volume":"15","author":"Roelens S.","year":"2009","journal-title":"Chem. Eur. J."},{"key":"e_1_2_7_7_1","doi-asserted-by":"crossref","first-page":"15008","DOI":"10.1021\/jacs.9b08257","volume":"141","author":"Hua B.","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_8_1","doi-asserted-by":"crossref","first-page":"4129","DOI":"10.1021\/ja7102179","volume":"130","author":"Wintergerst M. P.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_9_1","doi-asserted-by":"crossref","first-page":"2922","DOI":"10.1021\/ja0440295","volume":"127","author":"Mahoney J. M.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_10_1","doi-asserted-by":"crossref","first-page":"4451","DOI":"10.1039\/b308541d","volume":"23","author":"Evans A. J.","year":"2003","journal-title":"Dalton Trans."},{"key":"e_1_2_7_11_1","doi-asserted-by":"crossref","first-page":"5161","DOI":"10.1021\/jo00376a021","volume":"51","author":"Schmidtchen F.","year":"1986","journal-title":"J. Org. Chem."},{"key":"e_1_2_7_12_1","doi-asserted-by":"crossref","first-page":"1071","DOI":"10.1021\/ol034093b","volume":"5","author":"Ballistreri F. P.","year":"2003","journal-title":"Org. Lett."},{"key":"e_1_2_7_13_1","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1007\/1-4020-3687-6_9","volume-title":"Macrocyclic Chemistry: Current Trends and Future Perspectives","author":"Smith B. D.","year":"2005"},{"key":"e_1_2_7_14_1","doi-asserted-by":"crossref","first-page":"640","DOI":"10.5012\/bkcs.2002.23.4.640","volume":"23","author":"Kang S.-O.","year":"2002","journal-title":"Bull. Korean Chem. Soc."},{"key":"e_1_2_7_15_1","doi-asserted-by":"crossref","first-page":"5219","DOI":"10.1016\/S0040-4039(00)00819-4","volume":"41","author":"Tozawa T.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"e_1_2_7_16_1","doi-asserted-by":"crossref","first-page":"5846","DOI":"10.1021\/ja983970j","volume":"121","author":"Kubik S.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_17_1","doi-asserted-by":"crossref","first-page":"12281","DOI":"10.1021\/ja064012h","volume":"128","author":"Sessler J. L.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_18_1","doi-asserted-by":"crossref","first-page":"8827","DOI":"10.1021\/jacs.2c02924","volume":"144","author":"Hein R.","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_19_1","doi-asserted-by":"crossref","first-page":"21973","DOI":"10.1002\/anie.202108591","volume":"60","author":"Docker A.","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_19_2","doi-asserted-by":"crossref","first-page":"22144","DOI":"10.1002\/ange.202108591","volume":"133","year":"2021","journal-title":"Angew. Chem."},{"key":"e_1_2_7_20_1","doi-asserted-by":"crossref","first-page":"e202201838","DOI":"10.1002\/chem.202201838","volume":"28","author":"Kuhn H.","year":"2022","journal-title":"Chem. Eur. J."},{"key":"e_1_2_7_21_1","doi-asserted-by":"crossref","first-page":"11738","DOI":"10.1002\/chem.202101681","volume":"27","author":"Bickerton L. E.","year":"2021","journal-title":"Chem. Eur. J."},{"key":"e_1_2_7_22_1","doi-asserted-by":"crossref","first-page":"1588","DOI":"10.1021\/jacsau.1c00345","volume":"1","author":"Humeniuk H. V.","year":"2021","journal-title":"JACS Au"},{"key":"e_1_2_7_23_1","doi-asserted-by":"crossref","first-page":"5506","DOI":"10.1002\/ange.201801452","volume":"130","author":"Benz S.","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_24_1","doi-asserted-by":"crossref","first-page":"115482","DOI":"10.1016\/j.poly.2021.115482","volume":"209","author":"Bunchuay T.","year":"2021","journal-title":"Polyhedron"},{"key":"e_1_2_7_25_1","doi-asserted-by":"crossref","unstructured":"A. Docker Y.\u2005C. Tse H.\u2005M. Tay A.\u2005J. Taylor Z. Zhang P.\u2005D. Beer Angew. Chem. Int. Ed. 2022 61 e202214523 .","DOI":"10.1002\/anie.202214523"},{"key":"e_1_2_7_26_1","doi-asserted-by":"crossref","first-page":"14600","DOI":"10.1002\/chem.202102952","volume":"27","author":"Docker A.","year":"2021","journal-title":"Chem. Eur. J."},{"key":"e_1_2_7_27_1","doi-asserted-by":"crossref","first-page":"12800","DOI":"10.1039\/D1DT02414K","volume":"50","author":"Turner G.","year":"2021","journal-title":"Dalton Trans."},{"key":"e_1_2_7_28_1","doi-asserted-by":"crossref","first-page":"19442","DOI":"10.1002\/anie.202107748","volume":"60","author":"Docker A.","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_28_2","doi-asserted-by":"crossref","first-page":"19591","DOI":"10.1002\/ange.202107748","volume":"133","year":"2021","journal-title":"Angew. Chem."},{"key":"e_1_2_7_29_1","doi-asserted-by":"crossref","first-page":"3139","DOI":"10.1021\/acs.joc.5b00028","volume":"80","author":"Tepper R.","year":"2015","journal-title":"J. Org. Chem."},{"key":"e_1_2_7_30_1","doi-asserted-by":"crossref","first-page":"5740","DOI":"10.1021\/acs.orglett.5b02760","volume":"17","author":"Tepper R.","year":"2015","journal-title":"Org. Lett."},{"key":"e_1_2_7_31_1","doi-asserted-by":"crossref","first-page":"10559","DOI":"10.1021\/ja202096f","volume":"133","author":"Chudzinski M. G.","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_32_1","doi-asserted-by":"crossref","first-page":"4950","DOI":"10.1039\/D1CC01287H","volume":"57","author":"Tse Y. C.","year":"2021","journal-title":"Chem. Commun."},{"key":"e_1_2_7_33_1","doi-asserted-by":"crossref","first-page":"e202201209","DOI":"10.1002\/chem.202201209","volume":"28","author":"Munasinghe V. K.","year":"2022","journal-title":"Chem. Eur. J."},{"key":"e_1_2_7_34_1","doi-asserted-by":"crossref","first-page":"13376","DOI":"10.1039\/C7DT02832F","volume":"46","author":"Brown A.","year":"2017","journal-title":"Dalton Trans."},{"key":"e_1_2_7_35_1","doi-asserted-by":"crossref","first-page":"14972","DOI":"10.1021\/ja054862h","volume":"127","author":"Mele A.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_36_1","doi-asserted-by":"crossref","first-page":"2260","DOI":"10.1039\/C6CC09749A","volume":"53","author":"Tepper R.","year":"2017","journal-title":"Chem. Commun."},{"key":"e_1_2_7_37_1","doi-asserted-by":"crossref","first-page":"7837","DOI":"10.1002\/chem.202100579","volume":"27","author":"Docker A.","year":"2021","journal-title":"Chem. Eur. J."},{"key":"e_1_2_7_38_1","doi-asserted-by":"crossref","first-page":"12007","DOI":"10.1002\/anie.202001125","volume":"59","author":"Bunchuay T.","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_38_2","doi-asserted-by":"crossref","first-page":"12105","DOI":"10.1002\/ange.202001125","volume":"132","year":"2020","journal-title":"Angew. Chem."},{"key":"e_1_2_7_39_1","doi-asserted-by":"crossref","first-page":"2","DOI":"10.2174\/157017861101140113155347","volume":"11","author":"Hong B.","year":"2014","journal-title":"Lett. Org. Chem."},{"key":"e_1_2_7_40_1","doi-asserted-by":"crossref","first-page":"9299","DOI":"10.1039\/c2cc34392d","volume":"48","author":"Kniep F.","year":"2012","journal-title":"Chem. Commun."},{"key":"e_1_2_7_41_1","doi-asserted-by":"crossref","first-page":"724","DOI":"10.1039\/c0nj00780c","volume":"35","author":"Gromov S. P.","year":"2011","journal-title":"New J. Chem."},{"key":"e_1_2_7_42_1","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1007\/BF00662086","volume":"4","author":"Sheldrick W. S.","year":"1986","journal-title":"J. Inclusion Phenom."},{"key":"e_1_2_7_43_1","doi-asserted-by":"crossref","first-page":"9424","DOI":"10.1021\/acs.inorgchem.0c01346","volume":"59","author":"Martynov A. G.","year":"2020","journal-title":"Inorg. Chem."},{"key":"e_1_2_7_44_1","doi-asserted-by":"crossref","first-page":"825","DOI":"10.1039\/a800356d","volume":"7","author":"Beer P. D.","year":"1998","journal-title":"Chem. Commun."},{"key":"e_1_2_7_45_1","doi-asserted-by":"crossref","first-page":"1948","DOI":"10.1021\/acs.inorgchem.0c03408","volume":"60","author":"Lapkina L. A.","year":"2021","journal-title":"Inorg. Chem."},{"key":"e_1_2_7_46_1","unstructured":"http:\/\/app.supramolecular.org\/bindfit\/."},{"key":"e_1_2_7_47_1","doi-asserted-by":"crossref","first-page":"665","DOI":"10.1080\/10610278.2015.1118101","volume":"28","author":"Wageling N. B.","year":"2016","journal-title":"Supramol. Chem."},{"key":"e_1_2_7_48_1","doi-asserted-by":"crossref","first-page":"14793","DOI":"10.1039\/C5CC05495H","volume":"51","author":"Chakraborty S.","year":"2015","journal-title":"Chem. Commun."},{"key":"e_1_2_7_49_1","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1039\/C7FD00043J","volume":"203","author":"Scheiner S.","year":"2017","journal-title":"Faraday Discuss."},{"key":"e_1_2_7_50_1","unstructured":"Tetrakis 3 5-bis(trifluoromethyl)phenyl borate (BAr4F\u2212) salts were not used in order to not obscure the aromatic region of the titration1H NMR spectra."},{"key":"e_1_2_7_51_1","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1021\/acs.inorgchem.7b01983","volume":"57","author":"Lapkina L. A.","year":"2018","journal-title":"Inorg. Chem."}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202201170","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/asia.202201170","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202201170","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T13:16:54Z","timestamp":1759929414000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.202201170"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,28]]},"references-count":55,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2023,2]]}},"alternative-id":["10.1002\/asia.202201170"],"URL":"https:\/\/doi.org\/10.1002\/asia.202201170","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,28]]},"assertion":[{"value":"2022-11-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-12-28","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202201170"}}