{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T00:36:57Z","timestamp":1787618217947,"version":"build-2736575974"},"reference-count":47,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2022,10,31]],"date-time":"2022-10-31T00:00:00Z","timestamp":1667174400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"EU","award":["POPW.01.03.00-20-004\/11"],"award-info":[{"award-number":["POPW.01.03.00-20-004\/11"]}]},{"name":"EU","award":["4101.0000070"],"award-info":[{"award-number":["4101.0000070"]}]},{"name":"grant4students IDUB","award":["POPW.01.03.00-20-004\/11"],"award-info":[{"award-number":["POPW.01.03.00-20-004\/11"]}]},{"name":"grant4students IDUB","award":["4101.0000070"],"award-info":[{"award-number":["4101.0000070"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Two macrocyclic Schiff bases derived from o-phenylenediamine and 2-hydroxy-5-methylisophthalaldehyde L1 or 2-hydroxy-5-tert-butyl-1,3-benzenedicarboxaldehyde L2, respectively, were obtained and characterized by X-ray crystallography and spectroscopy (UV-vis, fluorescence and IR). X-ray crystal structure determination and DFT calculations for compounds confirmed their geometry in solution and in the solid phase. Moreover, intermolecular interactions in the crystal structure of L1 and L2 were analyzed using 3D Hirshfeld surfaces and the related 2D fingerprint plots. The 3D Hirschfeld analyses show that the most numerous interactions were found between hydrogen atoms. A considerable number of such interactions are justified by the presence of bulk tert-butyl groups in L2. The luminescence of L1 and L2 in various solvents and in the solid state was studied. In general, the quantum efficiency between 0.14 and 0.70 was noted. The increase in the quantum efficiency with the solvent polarity in the case of L1 was observed (\u03bbex = 350 nm). For L2, this trend is similar, except for the chloroform. In the solid state, emission was registered at 552 nm and 561 nm (\u03bbex = 350 nm) for L1 and L2, respectively. Thin layers of the studied compounds were deposited on Si(111) by the spin coating method or by thermal vapor deposition and studied by scanning electron microscopy (SEM\/EDS), atomic force microscopy (AFM), spectroscopic ellipsometry and fluorescence spectroscopy. The ellipsometric analysis of thin materials obtained by thermal vapor deposition showed that the band-gap energy was 3.45 \u00b1 0.02 eV (359 \u00b1 2 nm) and 3.29 \u00b1 0.02 eV (377 \u00b1 2 nm) for L1\/Si and L2\/Si samples, respectively. Furthermore, the materials of the L1\/Si and L2\/Si exhibited broad emission. This feature can allow for using these compounds in LED diodes.<\/jats:p>","DOI":"10.3390\/molecules27217396","type":"journal-article","created":{"date-parts":[[2022,11,1]],"date-time":"2022-11-01T06:01:28Z","timestamp":1667282488000},"page":"7396","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6616-337X","authenticated-orcid":false,"given":"Magdalena","family":"Barwiolek","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominika","family":"Jankowska","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4931-8701","authenticated-orcid":false,"given":"Anna","family":"Kaczmarek-K\u0119dziera","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Slawomir","family":"Wojtulewski","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Bia\u0142ystok, Ciolkowskiego 1K, 15-245 Bia\u0142ystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9416-1849","authenticated-orcid":false,"given":"Lukasz","family":"Skowro\u0144ski","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Kaliskiego 7, 85-796 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomasz","family":"Rerek","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Kaliskiego 7, 85-796 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1868-3690","authenticated-orcid":false,"given":"Pawe\u0142","family":"Popielarski","sequence":"additional","affiliation":[{"name":"Institute of Physics, Kazimierz Wielki University, Chodkiewicza 30, 85-064 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5220-4430","authenticated-orcid":false,"given":"Tadeusz M.","family":"Muziol","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Nicolaus Copernicus University in Torun, Gagarina 7, 87-100 Torun, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,31]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3299","DOI":"10.1016\/j.ejmech.2009.02.029","article-title":"Antimicrobial active macrocyclic complexes of Cr(III), Mn(III) and Fe(III) with their spectroscopic approach","volume":"44","author":"Singh","year":"2009","journal-title":"Eur. 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