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However, there is still a dearth of design strategies to expand the current library of zwitterionic ESIPT compounds. Herein, a novel zwitterionic excited\u2010state intramolecular proton transfer system is reported, enabled by addition of 1,4,7\u2010triazacyclononane (TACN) fragments on a dicyanomethylene\u20104H\u2010pyran (DCM) scaffold. The solvent\u2010dependent steady\u2010state photophysical studies, pKa measurements, and computational analysis strongly support that the ESIPT process is more efficient with two TACN groups attached to the DCM scaffold and not affected by polar protic solvents. Impressively, compound DCM\u2010OH\u20102\u2010DT exhibits a near\u2010infrared (NIR) emission at 740\u2005nm along with an uncommonly large Stokes shift. Moreover, DCM\u2010OH\u20102\u2010DT shows high affinity towards soluble amyloid \u03b2 (A\u03b2) oligomers in\u2005vitro and in 5xFAD mouse brain sections, and we have successfully applied DCM\u2010OH\u20102\u2010DT for the in\u2005vivo imaging of A\u03b2 aggregates and demonstrated its potential use as an early diagnostic agent for AD. Overall, this study can provide a general molecular design strategy for developing new zwitterionic ESIPT compounds with NIR emission in\u2005vivo imaging applications.<\/jats:p>","DOI":"10.1002\/chem.202302408","type":"journal-article","created":{"date-parts":[[2023,8,24]],"date-time":"2023-08-24T11:54:12Z","timestamp":1692878052000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Amphiphilic Molecules Exhibiting Zwitterionic Excited\u2010State Intramolecular Proton Transfer and Near\u2010Infrared Emission for the Detection of Amyloid \u03b2 Aggregates in Alzheimer's Disease**"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3592-9704","authenticated-orcid":false,"given":"Zhengxin","family":"Yu","sequence":"first","affiliation":[{"name":"Department of Chemistry Beckman Institute for Advanced Science and Technology The Neuroscience Program, Carle Illinois College of Medicine University of Illinois at Urbana-Champaign  600\u2005S. 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