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Here, 16 new receptor molecules were synthesized from two different 2,4,6\u2010trialkyl\u20101,3,5\u2010tris(bromomethyl)benzene starting materials via tris(isothiocyanatomethyl)benzene intermediates. The alkyl substituents in the benzene ring proved to be important for isothiocyanate group formation instead of competing thiocyanate group. The synthesis route allowed us to synthesize the isothiocyanate intermediates and further the receptor molecules without the typically used and highly toxic thiophosgene. The synthesized receptor molecules were used to study their halogen\u2010bond acceptor properties with diiodotetrafluorobenzene donors by single\u2010crystal X\u2010ray diffraction method. We were able to obtain five new crystal structures of halogen\u2010bonded complexes, in which all receptors showed two to four accepted C\u2212I\u22c5\u22c5\u22c5S halogen bonds. The observed halogen bonds were highly directional and showed large variation in C=S\u22c5\u22c5\u22c5I acceptor angles, indicating flexible acceptor properties of sulfur.<\/jats:p>","DOI":"10.1002\/asia.202300031","type":"journal-article","created":{"date-parts":[[2023,3,15]],"date-time":"2023-03-15T08:34:34Z","timestamp":1678869274000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Thiourea\u2010Based Tritopic Halogen\u2010Bonding Acceptors"],"prefix":"10.1002","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2923-4738","authenticated-orcid":false,"given":"Lauri","family":"Happonen","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Jyvaskyla  Survontie 9 B 40500 Jyv\u00e4skyl\u00e4"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Milla","family":"Mattila","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Jyvaskyla  Survontie 9 B 40500 Jyv\u00e4skyl\u00e4"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ivan","family":"Peshev","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Jyvaskyla  Survontie 9 B 40500 Jyv\u00e4skyl\u00e4"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Arttu","family":"Lehikoinen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Jyvaskyla  Survontie 9 B 40500 Jyv\u00e4skyl\u00e4"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2806-3807","authenticated-orcid":false,"given":"Arto","family":"Valkonen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Jyvaskyla  Survontie 9 B 40500 Jyv\u00e4skyl\u00e4"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,3,27]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC04518J"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.6b08438"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp801531w"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700986"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b02854"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.5b00513"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.1c00183"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501855"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501855"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502960"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201502960"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201702655"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201610884"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201610884"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00484"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1107\/S010876818400210X"},{"key":"e_1_2_8_14_1","first-page":"155","volume-title":"Halogen Bonding I: Impact on Materials Chemistry and Life Sciences","author":"Aaker\u00f6y C. 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