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The compounds show strikingly different emission spectra when bound to preformed A\u03b21\u201342 fibrils. This remarkable emission difference is retained when bound to amyloid fibrils of four distinct proteins, suggesting a common binding configuration for each molecule. Density functional theory calculations show that Py1SA is twisted, while Py2SA is more planar. Still, an analysis of the highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) of the two compounds indicates that the degree of electronic coupling between the pyrene and salicylic acid (SA) moieties is larger in Py1SA than in Py2SA. Excited state intramolecular proton transfer (ESIPT) coupled\u2010charge transfer (ICT) was observed for the anionic form in polar solvents. We conclude that ICT properties of <jats:italic>trans<\/jats:italic>\u2010stilbene derivatives can be utilized for amyloid probe design with large changes in emission spectra and decay times from analogous chemical structures depending on the detailed physical nature of the binding site.<\/jats:p>","DOI":"10.1002\/cphc.201800823","type":"journal-article","created":{"date-parts":[[2018,9,5]],"date-time":"2018-09-05T07:30:56Z","timestamp":1536132656000},"page":"3001-3009","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Intramolecular Proton and Charge Transfer of Pyrene\u2010based <i>trans<\/i>\u2010Stilbene Salicylic Acids Applied to Detection of Aggregated Proteins"],"prefix":"10.1002","volume":"19","author":[{"given":"Jun","family":"Zhang","sequence":"first","affiliation":[{"name":"Division of Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun","family":"Wang","sequence":"additional","affiliation":[{"name":"Division of Theoretical Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Sandberg","sequence":"additional","affiliation":[{"name":"Division of Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiongyu","family":"Wu","sequence":"additional","affiliation":[{"name":"Division of Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sofie","family":"Nystr\u00f6m","sequence":"additional","affiliation":[{"name":"Division of Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"suffix":"III","given":"Harry","family":"LeVine","sequence":"additional","affiliation":[{"name":"Sanders-Brown Center on Aging University of Kentucky  KY 40536\u20130230 Lexington USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Konradsson","sequence":"additional","affiliation":[{"name":"Division of Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Per","family":"Hammarstr\u00f6m","sequence":"additional","affiliation":[{"name":"Division of Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo","family":"Durbeej","sequence":"additional","affiliation":[{"name":"Division of Theoretical Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6649-7871","authenticated-orcid":false,"given":"Mikael","family":"Lindgren","sequence":"additional","affiliation":[{"name":"Division of Chemistry Department of Physics, Chemistry and Biology Link\u00f6ping University  581 83 Link\u00f6ping Sweden"},{"name":"Department of Physics Norwegian University of Science and Technology  7491 Trondheim Norway"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,10,8]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja991497j"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp052086u"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","first-page":"1998","author":"Gareis G.","journal-title":"Eur. 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