{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T15:17:23Z","timestamp":1790695043983,"version":"4.1.0"},"reference-count":47,"publisher":"American Chemical Society (ACS)","issue":"47","license":[{"start":{"date-parts":[[2020,11,16]],"date-time":"2020-11-16T00:00:00Z","timestamp":1605484800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccbyncnd_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R35GM133548"],"award-info":[{"award-number":["R35GM133548"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-1751370"],"award-info":[{"award-number":["CHE-1751370"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003246","name":"Nederlandse Organisatie voor Wetenschappelijk Onderzoek","doi-asserted-by":"publisher","award":["717.013.005"],"award-info":[{"award-number":["717.013.005"]}],"id":[{"id":"10.13039\/501100003246","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003246","name":"Nederlandse Organisatie voor Wetenschappelijk Onderzoek","doi-asserted-by":"publisher","award":["717.014.005"],"award-info":[{"award-number":["717.014.005"]}],"id":[{"id":"10.13039\/501100003246","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003246","name":"Nederlandse Organisatie voor Wetenschappelijk Onderzoek","doi-asserted-by":"publisher","award":["722.012.011"],"award-info":[{"award-number":["722.012.011"]}],"id":[{"id":"10.13039\/501100003246","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003246","name":"Nederlandse Organisatie voor Wetenschappelijk Onderzoek","doi-asserted-by":"publisher","award":["723.014.006"],"award-info":[{"award-number":["723.014.006"]}],"id":[{"id":"10.13039\/501100003246","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,11,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Despite a growing understanding of factors that drive monomer self-assembly to form supramolecular polymers, the effects of aromaticity gain have been largely ignored. Herein, we document the aromaticity gain in two different self-assembly modes of squaramide-based bolaamphiphiles. Importantly, O \u2192 S substitution in squaramide synthons resulted in supramolecular polymers with increased fiber flexibility and lower degrees of polymerization. Computations and spectroscopic experiments suggest that the oxo- and thiosquaramide bolaamphiphiles self-assemble into \u201chead-to-tail\u201d versus \u201cstacked\u201d arrangements, respectively. Computed energetic and magnetic criteria of aromaticity reveal that both modes of self-assembly increase the aromatic character of the squaramide synthons, giving rise to stronger intermolecular interactions in the resultant supramolecular polymer structures. These examples suggest that both hydrogen-bonding and stacking interactions can result in increased aromaticity upon self-assembly, highlighting its relevance in monomer design.<\/jats:p>","DOI":"10.1021\/jacs.0c02081","type":"journal-article","created":{"date-parts":[[2020,11,16]],"date-time":"2020-11-16T06:28:53Z","timestamp":1605508133000},"page":"19907-19916","source":"Crossref","is-referenced-by-count":50,"title":["Thiosquaramide-Based\nSupramolecular Polymers: Aromaticity\nGain in a Switched Mode of Self-Assembly"],"prefix":"10.1021","volume":"142","author":[{"given":"Victorio","family":"Saez Talens","sequence":"first","affiliation":[{"name":"Leiden University , , P.O. Box 9502, , ,","place":["Leiden, The Netherlands, 2300 RA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joyal","family":"Davis","sequence":"additional","affiliation":[{"name":"Leiden University , , P.O. Box 9502, , ,","place":["Leiden, The Netherlands, 2300 RA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chia-Hua","family":"Wu","sequence":"additional","affiliation":[{"name":"University of Houston , , , ,","place":["Houston, Texas, United States, 77204"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5678-0163","authenticated-orcid":true,"given":"Zhili","family":"Wen","sequence":"additional","affiliation":[{"name":"University of Houston , , , ,","place":["Houston, Texas, United States, 77204"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesca","family":"Lauria","sequence":"additional","affiliation":[{"name":"Leiden University , , P.O. Box 9502, , ,","place":["Leiden, The Netherlands, 2300 RA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3528-2912","authenticated-orcid":true,"given":"Karthick Babu Sai Sankar","family":"Gupta","sequence":"additional","affiliation":[{"name":"Leiden University , , P.O. Box 9502, , ,","place":["Leiden, The Netherlands, 2300 RA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raisa","family":"Rudge","sequence":"additional","affiliation":[{"name":"Leiden University , , P.O. Box 9502, , ,","place":["Leiden, The Netherlands, 2300 RA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mahsa","family":"Boraghi","sequence":"additional","affiliation":[{"name":"University of Houston , , , ,","place":["Houston, Texas, United States, 77204"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Hagemeijer","sequence":"additional","affiliation":[{"name":"Leiden University , , P.O. Box 9502, , ,","place":["Leiden, The Netherlands, 2300 RA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1721-6786","authenticated-orcid":true,"given":"Thuat T.","family":"Trinh","sequence":"additional","affiliation":[{"name":"Norwegian University of Science and Technology , , ,","place":["Trondheim, Norway, 7491"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pablo","family":"Englebienne","sequence":"additional","affiliation":[{"name":"Delft University of Technology , , Leeghwaterstraat 39 , ,","place":["Delft, The Netherlands, 2628 CB"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3543-4821","authenticated-orcid":true,"given":"Ilja K.","family":"Voets","sequence":"additional","affiliation":[{"name":"Eindhoven University of Technology , , P.O. Box 513, , ,","place":["Eindhoven, The Netherlands, 5600 MD"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0590-5290","authenticated-orcid":true,"given":"Judy I.","family":"Wu","sequence":"additional","affiliation":[{"name":"University of Houston , , , ,","place":["Houston, Texas, United States, 77204"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9152-1810","authenticated-orcid":true,"given":"Roxanne E.","family":"Kieltyka","sequence":"additional","affiliation":[{"name":"Leiden University , , P.O. Box 9502, , ,","place":["Leiden, The Netherlands, 2300 RA"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,11,16]]},"reference":[{"issue":"6070","key":"2026090217454851700_cit1","doi-asserted-by":"publisher","first-page":"813","DOI":"10.1126\/science.1205962","volume":"335","author":"Aida","year":"2012","journal-title":"Science"},{"issue":"18","key":"2026090217454851700_cit2","doi-asserted-by":"publisher","first-page":"6195","DOI":"10.1039\/c2cs35264h","volume":"41","author":"Appel","year":"2012","journal-title":"Chem. Soc. Rev."},{"issue":"4","key":"2026090217454851700_cit3","doi-asserted-by":"publisher","first-page":"2414","DOI":"10.1021\/acs.chemrev.5b00369","volume":"116","author":"Krieg","year":"2016","journal-title":"Chem. Rev."},{"issue":"May","key":"2026090217454851700_cit4","doi-asserted-by":"publisher","first-page":"7192","DOI":"10.1038\/453171a","volume":"453","author":"De Greef","year":"2008","journal-title":"Nature"},{"issue":"21","key":"2026090217454851700_cit5","doi-asserted-by":"publisher","first-page":"6621","DOI":"10.1039\/C7CS00564D","volume":"46","author":"Goor","year":"2017","journal-title":"Chem. Soc. Rev."},{"issue":"1","key":"2026090217454851700_cit6","doi-asserted-by":"publisher","first-page":"13","DOI":"10.1038\/nmat4474","volume":"15","author":"Webber","year":"2016","journal-title":"Nat. Mater."},{"issue":"43","key":"2026090217454851700_cit7","doi-asserted-by":"publisher","first-page":"14347","DOI":"10.1021\/jacs.6b08145","volume":"138","author":"Endo","year":"2016","journal-title":"J. Am. Chem. Soc."},{"issue":"14","key":"2026090217454851700_cit8","doi-asserted-by":"publisher","first-page":"4732","DOI":"10.1002\/anie.201813955","volume":"58","author":"Philips","year":"2019","journal-title":"Angew. Chem., Int.\nEd."},{"issue":"1","key":"2026090217454851700_cit9","doi-asserted-by":"publisher","first-page":"1623","DOI":"10.1038\/s41467-020-15422-6","volume":"11","author":"Aratsu","year":"2020","journal-title":"Nat.\nCommun."},{"issue":"12","key":"2026090217454851700_cit10","doi-asserted-by":"publisher","first-page":"2602","DOI":"10.1039\/C9QM00473D","volume":"3","author":"Sikder","year":"2019","journal-title":"Mater.\nChem. Front."},{"issue":"1","key":"2026090217454851700_cit11","doi-asserted-by":"publisher","first-page":"4760","DOI":"10.1038\/s41467-020-18587-2","volume":"11","author":"Han","year":"2020","journal-title":"Nat. Commun."},{"issue":"6","key":"2026090217454851700_cit12","doi-asserted-by":"publisher","first-page":"1606","DOI":"10.1002\/anie.201812217","volume":"58","author":"Sikder","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"issue":"14","key":"2026090217454851700_cit13","doi-asserted-by":"publisher","first-page":"2000173","DOI":"10.1002\/adom.202000173","volume":"8","author":"Das","year":"2020","journal-title":"Adv. Opt. Mater."},{"issue":"9","key":"2026090217454851700_cit14","doi-asserted-by":"publisher","first-page":"6030","DOI":"10.1039\/C7SC01730H","volume":"8","author":"Jalani","year":"2017","journal-title":"Chem. Sci."},{"issue":"16","key":"2026090217454851700_cit15","doi-asserted-by":"publisher","first-page":"1900577","DOI":"10.1002\/advs.201900577","volume":"6","author":"Markiewicz","year":"2019","journal-title":"Adv. Sci."},{"issue":"13","key":"2026090217454851700_cit16","doi-asserted-by":"publisher","first-page":"3516","DOI":"10.1002\/anie.201611715","volume":"56","author":"Pramanik","year":"2017","journal-title":"Angew.\nChem., Int. Ed."},{"issue":"5","key":"2026090217454851700_cit17","doi-asserted-by":"publisher","first-page":"5491","DOI":"10.1021\/acsnano.9b09610","volume":"14","author":"VandenBerg","year":"2020","journal-title":"ACS Nano"},{"issue":"14","key":"2026090217454851700_cit18","doi-asserted-by":"publisher","first-page":"5675","DOI":"10.1002\/anie.201911531","volume":"59","author":"Helmers","year":"2020","journal-title":"Angew. Chem., Int.\nEd."},{"issue":"45","key":"2026090217454851700_cit19","doi-asserted-by":"publisher","first-page":"18278","DOI":"10.1021\/jacs.9b09443","volume":"141","author":"Vantomme","year":"2019","journal-title":"J. Am. Chem. Soc."},{"issue":"26","key":"2026090217454851700_cit20","doi-asserted-by":"publisher","first-page":"9443","DOI":"10.1021\/ja503906p","volume":"136","author":"Krieg","year":"2014","journal-title":"J. Am. Chem. Soc."},{"issue":"39","key":"2026090217454851700_cit21","doi-asserted-by":"publisher","first-page":"13526","DOI":"10.1021\/ja507202f","volume":"136","author":"Wu","year":"2014","journal-title":"J. Am. Chem.\nSoc."},{"issue":"10","key":"2026090217454851700_cit22","doi-asserted-by":"publisher","first-page":"3427","DOI":"10.1021\/jacs.5b12703","volume":"138","author":"Kakeshpour","year":"2016","journal-title":"J. Am. Chem. Soc."},{"issue":"1","key":"2026090217454851700_cit23","doi-asserted-by":"publisher","first-page":"59","DOI":"10.1002\/jcc.23976","volume":"37","author":"Anand","year":"2016","journal-title":"J. Comput. Chem."},{"issue":"33","key":"2026090217454851700_cit24","doi-asserted-by":"publisher","first-page":"9842","DOI":"10.1002\/anie.201705023","volume":"56","author":"Kakeshpour","year":"2017","journal-title":"Angew. Chem., Int. Ed."},{"issue":"36","key":"2026090217454851700_cit25","doi-asserted-by":"publisher","first-page":"10502","DOI":"10.1002\/anie.201503905","volume":"54","author":"Saez Talens","year":"2015","journal-title":"Angew. Chem., Int. Ed."},{"issue":"24","key":"2026090217454851700_cit26","doi-asserted-by":"publisher","first-page":"7533","DOI":"10.1002\/chem.201103345","volume":"18","author":"Soberats","year":"2012","journal-title":"Chem.\n- Eur. J."},{"key":"2026090217454851700_cit27","doi-asserted-by":"publisher","first-page":"1398","DOI":"10.1016\/j.chempr.2019.02.027","volume":"5","author":"Marchetti","year":"2019","journal-title":"Chem."},{"issue":"1\u20132","key":"2026090217454851700_cit28","doi-asserted-by":"publisher","first-page":"115","DOI":"10.1016\/S0009-2614(01)01295-7","volume":"351","author":"Quin\u0303onero","year":"2002","journal-title":"Chem. Phys. Lett."},{"issue":"5","key":"2026090217454851700_cit29","doi-asserted-by":"publisher","first-page":"888","DOI":"10.1039\/C9OB02085C","volume":"18","author":"Bujosa","year":"2020","journal-title":"Org. Biomol. Chem."},{"issue":"9","key":"2026090217454851700_cit30","doi-asserted-by":"publisher","first-page":"3617","DOI":"10.1039\/C4SC01629G","volume":"5","author":"Busschaert","year":"2014","journal-title":"Chem. Sci."},{"issue":"30","key":"2026090217454851700_cit31","doi-asserted-by":"publisher","first-page":"7010","DOI":"10.1021\/jp025516e","volume":"106","author":"Lee","year":"2002","journal-title":"J. Phys. Chem.\nA"},{"issue":"9","key":"2026090217454851700_cit32","doi-asserted-by":"publisher","first-page":"3202","DOI":"10.1039\/c0ce00680g","volume":"13","author":"Lenthall","year":"2011","journal-title":"CrystEngComm"},{"issue":"6","key":"2026090217454851700_cit33","doi-asserted-by":"publisher","first-page":"452","DOI":"10.1039\/b701570d","volume":"9","author":"Custelcean","year":"2007","journal-title":"CrystEngComm"},{"issue":"4","key":"2026090217454851700_cit34","doi-asserted-by":"publisher","first-page":"680","DOI":"10.1107\/S0108768197002656","volume":"53","author":"Allen","year":"1997","journal-title":"Acta Crystallogr., Sect.\nB: Struct. Sci."},{"issue":"19","key":"2026090217454851700_cit35","doi-asserted-by":"publisher","first-page":"7430","DOI":"10.1021\/acs.macromol.9b01502","volume":"52","author":"De Windt","year":"2019","journal-title":"Macromolecules"},{"issue":"6371","key":"2026090217454851700_cit36","doi-asserted-by":"publisher","first-page":"72","DOI":"10.1126\/science.aam7588","volume":"359","author":"Yanagisawa","year":"2018","journal-title":"Science"},{"issue":"26","key":"2026090217454851700_cit37","doi-asserted-by":"publisher","first-page":"8642","DOI":"10.1002\/chem.201204273","volume":"19","author":"Mes","year":"2013","journal-title":"Chem. - Eur. J."},{"issue":"5","key":"2026090217454851700_cit38","doi-asserted-by":"publisher","first-page":"1442","DOI":"10.1021\/jo991589r","volume":"65","author":"Wang","year":"2000","journal-title":"J. Org. Chem."},{"issue":"1","key":"2026090217454851700_cit39","doi-asserted-by":"publisher","first-page":"16","DOI":"10.1186\/1751-0473-9-16","volume":"9","author":"Lamour","year":"2014","journal-title":"Source Code Biol.\nMed."},{"issue":"3\u20134","key":"2026090217454851700_cit40","doi-asserted-by":"publisher","first-page":"371","DOI":"10.1351\/pac196511030371","volume":"11","author":"Kasha","year":"1965","journal-title":"Pure Appl. Chem."},{"issue":"3","key":"2026090217454851700_cit41","doi-asserted-by":"publisher","first-page":"606","DOI":"10.1002\/chem.201904284","volume":"26","author":"Kartha","year":"2020","journal-title":"Chem. - Eur. J."},{"issue":"32","key":"2026090217454851700_cit42","doi-asserted-by":"publisher","first-page":"13482","DOI":"10.1021\/ja305512g","volume":"134","author":"Korevaar","year":"2012","journal-title":"J. Am. Chem. Soc."},{"issue":"14","key":"2026090217454851700_cit43","doi-asserted-by":"publisher","first-page":"4347","DOI":"10.1002\/chem.200902485","volume":"16","author":"Chierotti","year":"2010","journal-title":"Chem. - Eur. J."},{"key":"2026090217454851700_cit44","doi-asserted-by":"publisher","first-page":"1485","DOI":"10.3390\/sym2031485","volume":"2","author":"Raczyn\u0301ska","year":"2010","journal-title":"Symmetry"},{"issue":"10","key":"2026090217454851700_cit45","doi-asserted-by":"publisher","first-page":"3842","DOI":"10.1021\/cr030088+","volume":"105","author":"Chen","year":"2005","journal-title":"Chem. Rev."},{"issue":"26","key":"2026090217454851700_cit46","doi-asserted-by":"publisher","first-page":"6317","DOI":"10.1021\/ja960582d","volume":"118","author":"Schleyer","year":"1996","journal-title":"J. Am. Chem. Soc."},{"issue":"34","key":"2026090217454851700_cit47","doi-asserted-by":"publisher","first-page":"8291","DOI":"10.1021\/jp0724065","volume":"111","author":"Mo","year":"2007","journal-title":"J. Phys. Chem. A"}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.0c02081","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/142\/47\/19907\/67025348\/jacs.0c02081.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/142\/47\/19907\/67025348\/jacs.0c02081.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T21:45:53Z","timestamp":1788385553000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/142\/47\/19907\/617660\/Thiosquaramide-Based-Supramolecular-Polymers"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,16]]},"references-count":47,"journal-issue":{"issue":"47","published-online":{"date-parts":[[2020,11,16]]},"published-print":{"date-parts":[[2020,11,25]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.0c02081","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,11,16]]}}}