{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,6]],"date-time":"2026-09-06T05:15:20Z","timestamp":1788671720364,"version":"build-2803163510"},"reference-count":41,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T00:00:00Z","timestamp":1788480000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["31670596"],"award-info":[{"award-number":["31670596"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"award":["31670596"],"award-info":[{"award-number":["31670596"]}],"id":[{"id":"https:\/\/ror.org\/01h0zpd94","id-type":"ROR","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100009103","name":"Shaanxi Provincial Education Department","doi-asserted-by":"crossref","award":["25JK0455"],"award-info":[{"award-number":["25JK0455"]}],"id":[{"id":"10.13039\/501100009103","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100009103","name":"Shaanxi Provincial Education Department","doi-asserted-by":"crossref","award":["21JK0821"],"award-info":[{"award-number":["21JK0821"]}],"id":[{"id":"10.13039\/501100009103","id-type":"DOI","asserted-by":"crossref"}]},{"award":["25JK0455"],"award-info":[{"award-number":["25JK0455"]}],"id":[{"id":"https:\/\/ror.org\/05r16bb17","id-type":"ROR","asserted-by":"publisher"}]},{"award":["21JK0821"],"award-info":[{"award-number":["21JK0821"]}],"id":[{"id":"https:\/\/ror.org\/05r16bb17","id-type":"ROR","asserted-by":"publisher"}]},{"name":"Young Talent Fund of Association for Science and Technology in Shaanxi, China","award":["20260313"],"award-info":[{"award-number":["20260313"]}]},{"name":"Natural Science Basic Research Program of Shaanxi","award":["2026JC-YBQN-0198"],"award-info":[{"award-number":["2026JC-YBQN-0198"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Water-soluble alanine-functionalized perylene diimide derivatives (PDI-Ala) were synthesized by introducing alanine units at the imide positions of the PDI framework. Their photoluminescence properties and supramolecular aggregation behavior were investigated in solvents of varying polarity. Chiral L-PDI-Ala displayed distinct solvent-dependent emission colors and intensities, whereas the achiral PDI-Ala showed negligible emission under the same conditions. Poor solvents such as acetone and ethyl acetate promoted relatively efficient emission with hypsochromically shifted bands, while good solvents such as N, N-dimethylformamide and dimethyl sulfoxide induced bathochromically shifted emission with much lower quantum yields. The results indicate that strong face-to-face \u03c0-\u03c0 stacking in the solid-state leads to aggregation-caused quenching (ACQ), whereas ordered aggregates formed by intermolecular forces such as hydrogen bonds or stacking in solution can recover luminescence. On the basis of the spectroscopic and structural results, a solvent-regulated emission mechanism involving excimer\/exciplex formation together with H-type and J-type aggregation is proposed. This work provides useful insight into the aggregation-controlled optical behavior of chiral amino-acid-modified PDI materials and offers guidance for the design of chiroptical and self-assembled luminescent systems.<\/jats:p>","DOI":"10.3390\/molecules31173102","type":"journal-article","created":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T16:07:32Z","timestamp":1788538052000},"page":"3102","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Chiral Alanine Functionalized Perylene Diimides: Supramolecular Self-Assembly and Optical Properties"],"prefix":"10.3390","volume":"31","author":[{"given":"Di","family":"Fan","sequence":"first","affiliation":[{"name":"School of Artificial Intelligence, Shaanxi Polytechnic University, Xianyang 712000, China"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"conceptualization","vocabulary":"credit"},{"role":"writing-original-draft","vocabulary":"credit"},{"role":"methodology","vocabulary":"credit"},{"role":"investigation","vocabulary":"credit"},{"role":"software","vocabulary":"credit"}]},{"given":"Fan","family":"Qi","sequence":"additional","affiliation":[{"name":"School of Medicine, Xi\u2019an Peihua University, Xi\u2019an 710125, China"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"methodology","vocabulary":"credit"},{"role":"writing-review-editing","vocabulary":"credit"},{"role":"validation","vocabulary":"credit"}]},{"given":"Nan","family":"Li","sequence":"additional","affiliation":[{"name":"College of Chemistry and Materials Science, Weinan Normal University, Weinan 714099, China"},{"name":"Key Laboratory of Auxiliary Chemistry &Technology for Chemical Industry, Shaanxi University of Science & Technology, Ministry of Education, Xi\u2019an 710021, China"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"validation","vocabulary":"credit"},{"role":"formal-analysis","vocabulary":"credit"}]},{"given":"Rongli","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Medicine, Xi\u2019an Peihua University, Xi\u2019an 710125, China"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"visualization","vocabulary":"credit"},{"role":"investigation","vocabulary":"credit"}]},{"given":"Haitao","family":"Ren","sequence":"additional","affiliation":[{"name":"Shaanxi Key Laboratory of Liquid Crystal Polymer Intelligent Display, Technological Institute of Materials & Energy Science (TIMES), Xijing University, Xi\u2019an 710123, China"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"writing-review-editing","vocabulary":"credit"},{"role":"validation","vocabulary":"credit"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7935-0473","authenticated-orcid":false,"given":"Guodong","family":"Fan","sequence":"additional","affiliation":[{"name":"School of Medicine, Xi\u2019an Peihua University, Xi\u2019an 710125, China"},{"name":"Key Laboratory of Auxiliary Chemistry &Technology for Chemical Industry, Shaanxi University of Science & Technology, Ministry of Education, Xi\u2019an 710021, China"}],"role":[{"vocabulary":"crossref","role":"author"},{"role":"funding-acquisition","vocabulary":"credit"},{"role":"project-administration","vocabulary":"credit"},{"role":"supervision","vocabulary":"credit"},{"role":"writing-review-editing","vocabulary":"credit"}]}],"member":"1968","published-online":{"date-parts":[[2026,9,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1021\/jacs.1c11544","article-title":"High-Performance Organic Electronic Materials by Contorting Perylene Diimides","volume":"144","author":"Schaack","year":"2022","journal-title":"J. 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