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The compound is a diphenylalanine derivative belonging to a family of aromatic dipeptides that spontaneously self-organize into nanostructures through molecular recognition. The dipeptide exhibits several step-like peaks in its absorption band, indicative of self-assembly into quantum-confined nanostructures. In contrast, the parent Boc-p-nitro-L-phenylalanine amino acid lacks these features, indicating that the tyrosine residue favors quantum-confined self-assembly. Crystal structure determination reveals distinct packing styles: Boc-p-nitro-L-phenylalanine forms two-dimensional hydrogen-bonded layers, while the related p-nitro-free Boc-L-phenylalanyl-tyrosine dipeptide organizes into a 3D helical columnar architecture, driven by the additional hydrogen-bonding capacity of the peptide bond and tyrosine hydroxyl group, which favors the formation of a channel-type tetragonal architecture network over the planar sheets of the monomer. Furthermore, the introduction of a tyrosine residue into the Boc-p-nitro-L-phenylalanine molecule alters its supramolecular assembly, as the dipeptide Boc-p-nitro-L-phenylalanyl-tyrosine crystallizes as a monohydrate. The water molecule present in the structure acts as a bridge, participating in a hydrogen-bonding network between the tyrosine hydroxyl groups of neighboring columns through intermolecular interactions.<\/jats:p>","DOI":"10.3390\/ma19071319","type":"journal-article","created":{"date-parts":[[2026,3,26]],"date-time":"2026-03-26T13:48:41Z","timestamp":1774532921000},"page":"1319","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Self-Assembly and Crystal Structure of Boc-Protected Dipeptides Containing L-Phenylalanine and L-Tyrosine"],"prefix":"10.3390","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5380-9212","authenticated-orcid":false,"given":"Rosa M. F.","family":"Baptista","sequence":"first","affiliation":[{"name":"Centre of Physics of Minho and Porto Universities (CF-UM-UP), Laboratory of Physics for Materials and Emerging Technology (LaPMET), University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9247-6780","authenticated-orcid":false,"given":"Alejandro P.","family":"Ayala","sequence":"additional","affiliation":[{"name":"Departamento de F\u00edsica, Universidade Federal do Cear\u00e1, Fortaleza 65455-900, CE, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3672-0045","authenticated-orcid":false,"given":"Clara S. B.","family":"Gomes","sequence":"additional","affiliation":[{"name":"i4HB, NOVA School of Science and Technology, NOVA University Lisbon, 2829-516 Caparica, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-9133-9812","authenticated-orcid":false,"given":"Daniela","family":"Santos","sequence":"additional","affiliation":[{"name":"Centre of Physics of Minho and Porto Universities (CF-UM-UP), Laboratory of Physics for Materials and Emerging Technology (LaPMET), University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7968-5038","authenticated-orcid":false,"given":"Michael S.","family":"Belsley","sequence":"additional","affiliation":[{"name":"Centre of Physics of Minho and Porto Universities (CF-UM-UP), Laboratory of Physics for Materials and Emerging Technology (LaPMET), University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0862-1683","authenticated-orcid":false,"given":"Etelvina","family":"de Matos Gomes","sequence":"additional","affiliation":[{"name":"Centre of Physics of Minho and Porto Universities (CF-UM-UP), Laboratory of Physics for Materials and Emerging Technology (LaPMET), University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2026,3,26]]},"reference":[{"key":"ref_1","first-page":"U1154","article-title":"Self-assembly of peptide nanotubes by charged-termini capped diphenylailanine peptide analogue","volume":"Volume 229","author":"Gazit","year":"2005","journal-title":"Abstracts of Papers of the American Chemical Society"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"8138","DOI":"10.1021\/acsnano.8b03118","article-title":"Diphenylalanine Peptide Nanotube Energy Harvesters","volume":"12","author":"Lee","year":"2018","journal-title":"ACS Nano"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"4448","DOI":"10.1021\/nn2016524","article-title":"Charged Diphenylalanine Nanotubes and Controlled Hierarchical Self-Assembly","volume":"5","author":"Wang","year":"2011","journal-title":"ACS Nano"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"e1707083","DOI":"10.1002\/adma.201707083","article-title":"Tailor-Made Functional Peptide Self-Assembling Nanostructures","volume":"30","author":"Amit","year":"2018","journal-title":"Adv. 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