{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,13]],"date-time":"2026-05-13T16:17:59Z","timestamp":1778689079001,"version":"3.51.4"},"reference-count":92,"publisher":"Wiley","issue":"66","license":[{"start":{"date-parts":[[2020,10,19]],"date-time":"2020-10-19T00:00:00Z","timestamp":1603065600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001475","name":"Nanyang Technological University","doi-asserted-by":"publisher","award":["041NS000171C230"],"award-info":[{"award-number":["041NS000171C230"]}],"id":[{"id":"10.13039\/501100001475","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2020,11,26]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Monobromo\u2010, tetrabromo\u2010, and pentachloro\u2010corannulene are subjected to nucleophilic substitution reactions with tolyl selenide and phenyl telluride\u2010based nucleophiles generated in situ from the corresponding dichalcogenides. In the case of selenium nucleophile, the reaction provides moderate yields (52\u201377\u2009%) of the targeted corannulene selenoethers. A subsequent oxidation of the selenium atoms proceeds smoothly to furnish corannulene selenones in 81\u201393\u2009% yield. In the case of tellurides, only monosubstitution of the corannulene scaffold could be achieved albeit with concomitant oxidation of the tellerium atom. Unexpectedly, this monotelluroxide derivative of corannulene (RR'Te=O, R=Ph, R\u2019=corannulene) is observed to form a linear coordination polymer chain in the crystalline state. In this chain, Te\u2010O constitutes the polymer backbone around which the aromatic groups (R and R\u2019) arrange as polymer side\u2010chains. The polymer crystal is stabilized through intramolecular \u03c0\u2013\u03c0 stacking interactions of the side\u2010chains and intermolecular hydrogen and halogen bonding interactions with the solvent (chloroform) molecules. Interestingly, each diad of the polymer chain is racemic. Therefore, in terms of stereoregularity, the polymer chain can be described as syndiotactic.<\/jats:p>","DOI":"10.1002\/chem.202003989","type":"journal-article","created":{"date-parts":[[2020,9,25]],"date-time":"2020-09-25T11:14:45Z","timestamp":1601032485000},"page":"15135-15139","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Selenium and Tellurium Derivatives of Corannulene: Serendipitous Discovery of a One\u2010Dimensional Stereoregular Coordination Polymer Crystal Based on Te\u2010O Backbone and Side\u2010Chain Aromatic Array"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5342-2985","authenticated-orcid":false,"given":"Viktor","family":"Bar\u00e1t","sequence":"first","affiliation":[{"name":"Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore  21-Nanyang Link 637371 Singapore Singapore"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8663-6189","authenticated-orcid":false,"given":"Mihaiela C.","family":"Stuparu","sequence":"additional","affiliation":[{"name":"Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University Singapore  21-Nanyang Link 637371 Singapore Singapore"},{"name":"School of Materials Science and Engineering Nanyang Technological University  50 Nanyang Avenue 639798 Singapore Singapore"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,10,19]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00954a049"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00736a028"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00018a082"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja953734y"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0011461"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/op200387s"},{"key":"e_1_2_2_8_1","unstructured":"For review articles covering the area see:"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050553y"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050554q"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201001585"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.130984"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1562469"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/smll.201503950"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.7b02245"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00141"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC02179A"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QM00593H"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201803927"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-019-0160-1"},{"key":"e_1_2_2_21_1","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja016761z"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol027565f"},{"key":"e_1_2_2_24_2","first-page":"173","volume":"1","author":"Bancu M.","year":"2004","journal-title":"Synlett"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja808396b"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/B919616A"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201601405"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.7b00807"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201700861"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC00327D"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905521"},{"key":"e_1_2_2_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201801311"},{"key":"e_1_2_2_33_1","unstructured":"For derivatives in which the selenium atom is not directly attached to the aromatic scaffold see:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0019981"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00242-3"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2040688"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b00053"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.350"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-20699-3_7"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00434E"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2018.02.036"},{"key":"e_1_2_2_43_1","unstructured":"\u00a0"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1369-7021(08)70054-3"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmat2966"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00725A"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201810611"},{"key":"e_1_2_2_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201810611"},{"key":"e_1_2_2_48_1","unstructured":"For three-dimensional coordination buckybowl polymers see:"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201509557"},{"key":"e_1_2_2_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201509557"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612199"},{"key":"e_1_2_2_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612199"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201806202"},{"key":"e_1_2_2_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201806202"},{"key":"e_1_2_2_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/om021024c"},{"key":"e_1_2_2_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/cnma.201600076"},{"key":"e_1_2_2_54_1","unstructured":"The only general class of tellurium main-chain polymers is restricted to tellurophenes. For review articles covering this area of research see:"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma502307b"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC04023C"},{"key":"e_1_2_2_57_1","unstructured":"For oligomers\/polymers carrying corannulene see:"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303032"},{"key":"e_1_2_2_58_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303032"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.26038"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b12468"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmacrolett.7b00746"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300830"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.2533\/chimia.2011.799"},{"key":"e_1_2_2_64_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob40464a"},{"key":"e_1_2_2_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.10.075"},{"key":"e_1_2_2_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja991310o"},{"key":"e_1_2_2_67_1","unstructured":"\u00a0"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)01785-8"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00251-4"},{"key":"e_1_2_2_70_1","unstructured":"\u00a0"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja991486q"},{"key":"e_1_2_2_72_2","unstructured":"P.-C. Cheng PhD Dissertation Boston College 1996."},{"key":"e_1_2_2_73_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.10.067"},{"key":"e_1_2_2_74_1","unstructured":"Deposition Number 1996925contains 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 servicewww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_2_75_1","unstructured":"\u00a0"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt9820000709"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1515\/znb-2002-0203"},{"key":"e_1_2_2_78_1","unstructured":"\u00a0"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms11299"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2017.01.009"},{"key":"e_1_2_2_81_1","unstructured":"\u00a0"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1080\/10426500902947476"},{"key":"e_1_2_2_83_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2019.05.003"},{"key":"e_1_2_2_84_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712011"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201712011"},{"key":"e_1_2_2_85_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199216361"},{"key":"e_1_2_2_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19921041242"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202003989","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202003989","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202003989","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T17:03:46Z","timestamp":1760288626000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202003989"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,10,19]]},"references-count":92,"journal-issue":{"issue":"66","published-print":{"date-parts":[[2020,11,26]]}},"alternative-id":["10.1002\/chem.202003989"],"URL":"https:\/\/doi.org\/10.1002\/chem.202003989","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,10,19]]},"assertion":[{"value":"2020-09-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-10-19","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}