{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T06:59:27Z","timestamp":1790319567130,"version":"4.1.0"},"reference-count":53,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T00:00:00Z","timestamp":1790208000000},"content-version":"vor","delay-in-days":23,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPlusChem"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:p>\n                    Conformational bias plays a crucial role in host\u2013guest complex. Due to spatial arrangements of binding sites, binding affinities of conformers differ significantly toward a guest. Consequently, isolation of conformers is a prerequisite in understanding host\u2013guest complexes. Herein, we report the synthesis and separation of naphthalene\u2010functionalized resorcin[4]arenes in two distinct conformations: chair and crown. The use of bulky naphthalene as a pendant at methylene bridge results in steric strain, yielding conformationally nonconvertible isomers, with large difference in dipole moment (\u0394\n                    <jats:italic>\u03bc<\/jats:italic>\n                    \u2009=\u20096.83\u2009D), facilitating their separation by traditional column chromatography. The isomers were characterized by NMR, mass, and X\u2010ray diffraction analysis. Notably, in polar solvent, the crown isomer undergoes a conformational change to boat, in the upper rim, coupled with rotation of naphthalene in the lower rim. The solvent\u2010dependent conformational and rotational change results in an electron\u2010rich cavity in the lower rim in nonpolar solvent that binds with electron\u2010deficient nitroaromatics. While the incorporation of naphthalene in the lower rim overcomes the bottleneck of separation of distinct conformers, the conformation\u2010specific binding in the lower rim diversifies its applications beyond cation binding and paves a new direction in hosting guests in the lower rim which remained underexplored so far.\n                  <\/jats:p>","DOI":"10.1002\/cplu.70256","type":"journal-article","created":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T13:34:52Z","timestamp":1790256892000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Lower Rim Naphthyl\u2010Functionalized Resorcin[4]arene Conformers: Column Chromatographic Separation and Adaptive Molecular Recognition"],"prefix":"10.1002","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-5068-1815","authenticated-orcid":false,"given":"Initha","family":"Venkatesan","sequence":"first","affiliation":[{"name":"Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology  Kattankulathur Tamil Nadu India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aarthi","family":"Sakthivel","sequence":"additional","affiliation":[{"name":"Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology  Kattankulathur Tamil Nadu India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2849-5784","authenticated-orcid":false,"given":"Narayan Ch.","family":"Jana","sequence":"additional","affiliation":[{"name":"Centre of Innovation and Research\u2010Centre for Next Generation Materials and Technology (COIR\u2010CNGMT) Kalinga Institute of Industrial Technology (KIIT) Deemed to be University  Bhubaneswar Odisha India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mercy Abarna","family":"Anandharaj","sequence":"additional","affiliation":[{"name":"Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology  Kattankulathur Tamil Nadu India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wilson Raphel","family":"John Britto","sequence":"additional","affiliation":[{"name":"Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology  Kattankulathur Tamil Nadu India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5623-439X","authenticated-orcid":false,"given":"Susnata","family":"Pramanik","sequence":"additional","affiliation":[{"name":"Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology  Kattankulathur Tamil Nadu India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4104-4774","authenticated-orcid":false,"given":"Jayanta","family":"Samanta","sequence":"additional","affiliation":[{"name":"Department of Chemistry College of Engineering and Technology SRM Institute of Science and Technology  Kattankulathur Tamil Nadu India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,24]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0506478"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200900814"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10847-013-0336-8"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20688"},{"key":"e_1_2_9_6_1","first-page":"1539","article-title":"Dehydrative Amination of Alcohols in Water Using a Water\u2010Soluble Calix[4]Resorcinarene Sulfonic Acid","volume":"10","author":"Shirakawa S.","year":"2008","journal-title":"Synlett"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/B813373E"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol203243j"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2008.09.015"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201805206"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja027982n"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/b207875a"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c11793"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules29245854"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202017035"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/b714735j"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202001582"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905805"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol100407f"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00341G"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol400118t"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202305005"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12894"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.75.393"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00153B"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000573"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja982970g"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201700725"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol061097i"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2023.108559"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2022.134571"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.5c00295"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.04.114"},{"key":"e_1_2_9_34_1","first-page":"2051282","article-title":"One\u2010Step Synthesis of Rccc\u2010 and Rctt\u2010Diastereomers of Novel Calix[4]Resorcinols Based on a Para\u2010Thiophosphorylated Derivative of Benzaldehyde","volume":"2019","author":"Castillo\u2010Aguirre A. A.","year":"2019","journal-title":"Journal of Analytical Methods in Chemistry"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201603090"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.2c03218"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1080\/17518253.2023.2290847"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c00128"},{"key":"e_1_2_9_39_1","unstructured":"Deposition numbers 2555005 (for 1chair) and 2555006 (for 1crown) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25102275"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1MA00478F"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202301985"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC06225F"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201504126"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4DT01771D"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.08.083"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c03784"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.9b02855"},{"key":"e_1_2_9_49_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA02758F"},{"key":"e_1_2_9_50_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules30193901"},{"key":"e_1_2_9_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.0c03060"},{"key":"e_1_2_9_52_1","doi-asserted-by":"publisher","DOI":"10.36306\/konjes.1573403"},{"key":"e_1_2_9_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2016.06.045"},{"key":"e_1_2_9_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202302029"}],"container-title":["ChemPlusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cplu.70256","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cplu.70256","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cplu.70256","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T06:09:45Z","timestamp":1790316585000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cplu.70256"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9]]},"references-count":53,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2026,9]]}},"alternative-id":["10.1002\/cplu.70256"],"URL":"https:\/\/doi.org\/10.1002\/cplu.70256","archive":["Portico"],"relation":{},"ISSN":["2192-6506","2192-6506"],"issn-type":[{"value":"2192-6506","type":"print"},{"value":"2192-6506","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9]]},"assertion":[{"value":"2026-07-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-11","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-24","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70256"}}