{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T00:28:07Z","timestamp":1760228887080,"version":"build-2065373602"},"reference-count":42,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2022,5,25]],"date-time":"2022-05-25T00:00:00Z","timestamp":1653436800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["UIDB\/00313\/2020 and UIDP\/00313\/2020"],"award-info":[{"award-number":["UIDB\/00313\/2020 and UIDP\/00313\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006369","name":"Bitlis Eren University","doi-asserted-by":"publisher","award":["BEBAP-2014.05 and BEBAP-2013.04"],"award-info":[{"award-number":["BEBAP-2014.05 and BEBAP-2013.04"]}],"id":[{"id":"10.13039\/501100006369","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100018388","name":"Eskisehir Technical University","doi-asserted-by":"publisher","award":["No number"],"award-info":[{"award-number":["No number"]}],"id":[{"id":"10.13039\/100018388","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Photochem"],"abstract":"<jats:p>A new benzyloxy containing ortho hydroxyl-substituted aryl Schiff base, trans 2-((2-(benzyloxy)benzylidene) amino)phenol (abbreviated as BBAP), was synthesized and characterized by 1H-, 13C-NMR and infrared spectroscopic techniques and elemental analysis. The conformational landscape of the compound, as well as its infrared spectra in argon and N2 cryogenic matrices (10 K) were investigated, followed by the study of the effects of in situ UV irradiation of the matrix-isolated compound. The structural information was obtained through an extensive series of quantum chemical calculations performed at the DFT(B3LYP)\/6-311++G(d,p) level of theory, which enabled to identify 3 low-energy OH\u00b7\u00b7\u00b7N intramolecularly H-bonded conformers of the molecule that were later found to be present in the as-deposited cryogenic matrices. The 3 experimentally relevant conformers of BBAP differ in the geometry of the benzyloxy substituent, and were discovered to interconvert upon in situ UV irradiation (\u03bb = 230 nm) of the matrix-isolated compound. This is the first report on UV-induced conformational changes taking place in a benzyloxy fragment for a matrix-isolated compound.<\/jats:p>","DOI":"10.3390\/photochem2020026","type":"journal-article","created":{"date-parts":[[2022,5,25]],"date-time":"2022-05-25T08:41:33Z","timestamp":1653468093000},"page":"376-389","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["UV-Induced Benzyloxy Rotamerization in an Ortho OH-Substituted Aryl Schiff Base"],"prefix":"10.3390","volume":"2","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4410-0831","authenticated-orcid":false,"given":"\u0130sa","family":"S\u0131d\u0131r","sequence":"first","affiliation":[{"name":"Department of Physics, Bitlis Eren University, 13000 Bitlis, Turkey"},{"name":"CQC-IMS, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5329-2815","authenticated-orcid":false,"given":"Yadigar","family":"G\u00fclseven S\u0131d\u0131r","sequence":"additional","affiliation":[{"name":"Department of Physics, Bitlis Eren University, 13000 Bitlis, Turkey"},{"name":"CQC-IMS, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7039-8099","authenticated-orcid":false,"given":"S\u00e1ndor","family":"G\u00f3bi","sequence":"additional","affiliation":[{"name":"CQC-IMS, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"},{"name":"MTA-ELTE Lend\u00fclet Laboratory Astrochemistry Research Group, Institute of Chemistry, ELTE E\u00f6tv\u00f6s Lor\u00e1nd University, H-1518 Budapest, Hungary"}]},{"given":"Halil","family":"Berber","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Eski\u015fehir Technical University, 26470 Eski\u015fehir, Turkey"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8264-6854","authenticated-orcid":false,"given":"Rui","family":"Fausto","sequence":"additional","affiliation":[{"name":"CQC-IMS, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1021\/cr0683616","article-title":"Metal-Free Methods in the Synthesis of Macrocyclic Schiff Bases","volume":"107","author":"Borisova","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1311","DOI":"10.1016\/j.ccr.2006.11.016","article-title":"The development of compartmental macrocyclic Schiff bases and related polyamine derivatives","volume":"251","author":"Vigato","year":"2007","journal-title":"Coord. Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3243","DOI":"10.1016\/j.corsci.2005.11.016","article-title":"The application of some polydentate Schiff base compounds containing aminic nitrogens as corrosion inhibitors for mild steel in acidic media","volume":"48","author":"Atakol","year":"2006","journal-title":"Corros. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3055","DOI":"10.1016\/j.ccr.2005.05.003","article-title":"Ruthenium complexes bearing bidentate Schiff base ligands as efficient catalysts for organic and polymer syntheses","volume":"249","author":"Drozdzak","year":"2005","journal-title":"Coord. Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"816","DOI":"10.1016\/j.ccr.2005.10.007","article-title":"Uranium complexes of multidentate N-donor ligands","volume":"250","author":"Sessler","year":"2006","journal-title":"Coord. Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1180","DOI":"10.1021\/ma00108a054","article-title":"Conjugated aromatic polyimines. 2. Synthesis, structure, and properties of new aromatic polyazomethines","volume":"28","author":"Yang","year":"1995","journal-title":"Macromolecules"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1021\/ma970756r","article-title":"3-Hexyl Tetra-Substituted Sesquithienylene- Phenylene Polyazomethines with High Molecular Weight. Mechanistic Considerations","volume":"31","author":"Destri","year":"1998","journal-title":"Macromolecules"},{"key":"ref_8","first-page":"927","article-title":"Poly(azomethine)s","volume":"46","author":"Grigoras","year":"2001","journal-title":"Rev. Roum. Chim."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"4859","DOI":"10.1016\/S0032-3861(00)00883-1","article-title":"The synthesis and properties of oligosalicylaldehyde and its Schiff base oligomers","volume":"42","author":"Kaya","year":"2001","journal-title":"Polymer"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"506","DOI":"10.1016\/j.cplett.2004.10.129","article-title":"Biological nano-ceramic materials for holographic data storage","volume":"400","author":"Wu","year":"2004","journal-title":"Chem. Phys. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"156","DOI":"10.1002\/adma.200400953","article-title":"A novel thermally stable spironaphthoxazine and its application in rewritable high density optical data storage","volume":"17","author":"Yuan","year":"2005","journal-title":"Adv. Mater."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2219","DOI":"10.1021\/am900587u","article-title":"Photosensitive polymeric materials for two-photon 3D WORM optical data storage systems","volume":"1","author":"Yanez","year":"2009","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"9310","DOI":"10.1021\/ja906733q","article-title":"Modeling, preparation, and characterization of a dipole moment switch driven by Z\/E photoisomerization","volume":"132","author":"Melloni","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"27539","DOI":"10.1021\/jp5081884","article-title":"Photoswitching of conductance through salicylidene methylamine","volume":"118","author":"Staykov","year":"2014","journal-title":"J. Phys. Chem. C"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"499","DOI":"10.1016\/j.saa.2014.03.090","article-title":"Anion recognition by simple chromogenic and chromo-fluorogenic salicylidene Schiff base or reduced-Schiff base receptors","volume":"129","author":"Dalapati","year":"2014","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4918","DOI":"10.1021\/cr400568b","article-title":"Recent advances in development of chiral fluorescent and colorimetric sensors","volume":"114","author":"Zhang","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_17","first-page":"579","article-title":"Photochromism and thermochromism of Schiff bases in the solid state: Structural aspects","volume":"33","author":"Hadjoudis","year":"2004","journal-title":"Chem. Soc. Rev."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.jphotochemrev.2005.12.002","article-title":"Photochromism of organic compounds in the crystal state","volume":"6","author":"Amimoto","year":"2005","journal-title":"J. Photochem. Photobiol. C Photochem. Rev."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1563","DOI":"10.1021\/jo00292a035","article-title":"The role of catalysts in the air oxidation of aliphatic aldehydes","volume":"55","author":"Larkin","year":"1990","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.jtemb.2004.07.003","article-title":"Antiradical activity of different copper (II) Schiff base complexes and their effect on alloxan-induced diabetes","volume":"18","year":"2004","journal-title":"J. Trace Elem. Med. Biol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"949","DOI":"10.1016\/j.saa.2009.08.045","article-title":"Characteristic and spectroscopic properties of the Schiff-base model compounds","volume":"74","author":"Kaczmarczyk","year":"2009","journal-title":"Spectrochim. Acta. A. Mol. Biomol. Spectrosc."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Raczuk, E., Dmochowska, B., Samaszko-Fiertek, J., and Madaj, J. (2022). Different Schiff Bases\u2014Structure, Importance and Classification. Molecules, 27.","DOI":"10.3390\/molecules27030787"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2131","DOI":"10.1021\/jp035009c","article-title":"Proton Transfer Equilibria in Schiff Bases with Steric Repulsion","volume":"108","author":"Filarowski","year":"2004","journal-title":"J. Phys. Chem. A"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1016\/j.molstruc.2011.05.029","article-title":"Tautomeric Schiff bases: Iono-, solvato-, thermo-and photochromism","volume":"998","author":"Minkin","year":"2011","journal-title":"J. Mol. Struct."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1096","DOI":"10.1016\/j.molliq.2017.07.070","article-title":"Study on the electronic and photophysical properties of the substitute-((2-phenoxybenzylidene) amino) phenol derivatives: Synthesis, solvatochromism, electric dipole moments and DFT calculations","volume":"242","author":"Pirbudak","year":"2017","journal-title":"J. Mol. Liq."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"775","DOI":"10.1007\/s10953-019-00885-z","article-title":"The Dipole Moments and Solvatochromism of ((4-(Benzyloxy) benzylidene) amino) phenol Compounds as Solvatochromic Materials","volume":"48","author":"Berber","year":"2019","journal-title":"J. Solut. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"835","DOI":"10.1007\/s11224-018-1228-8","article-title":"The electronic structure, solvatochromism, and electric dipole moments of new Schiff base derivatives using absorbance and fluorescence spectra","volume":"30","author":"Aslan","year":"2019","journal-title":"Struct. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1016\/j.chemphys.2014.10.007","article-title":"Solid state photochromism and thermochromism of two related N-salicylidene anilines","volume":"444","author":"Avadanei","year":"2014","journal-title":"Chem. Phys."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"S\u0131d\u0131r, \u0130., S\u0131d\u0131r, Y.G., G\u00f3bi, S., Berber, H., Ildiz, G.O., and Fausto, R. (2022). UV-induced \u2013OCH3 rotamerization in a matrix-isolated methoxy-substituted ortho-hydroxyaryl Schiff base. Photochem. Photobiol. Sci.","DOI":"10.1007\/s43630-021-00166-z"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"S\u0131d\u0131r, \u0130., G\u00fclseven S\u0131d\u0131r, Y., G\u00f3bi, S., Berber, H., and Fausto, R. (2021). Structural Relevance of Intramolecular H-Bonding in Ortho-Hydroxyaryl Schiff Bases: The Case of 3-(5-bromo-2-hydroxybenzylideneamino) Phenol. Molecules, 26.","DOI":"10.3390\/molecules26092814"},{"key":"ref_31","unstructured":"Frisch, M., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2009). Gaussian 09, Gaussian, Inc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","article-title":"Density-functional exchange-energy approximation with correct asymptotic behavior","volume":"38","author":"Becke","year":"1988","journal-title":"Phys. Rev. A"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B Condens. Matter"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1200","DOI":"10.1139\/p80-159","article-title":"Accurate spin-dependent electron liquid correlation energies for local spin density calculations: A critical analysis","volume":"58","author":"Vosko","year":"1980","journal-title":"Can. J. Phys."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"5639","DOI":"10.1063\/1.438980","article-title":"Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z = 11\u201318","volume":"72","author":"McLean","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1063\/1.438955","article-title":"Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions","volume":"72","author":"Krishnan","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3265","DOI":"10.1063\/1.447079","article-title":"Self-consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets","volume":"80","author":"Frisch","year":"1984","journal-title":"J. Chem. Phys."},{"key":"ref_38","unstructured":"(2022, January 03). Chemcraft\u2014Graphical Program for Visualization of Quantum Chemistry Computations. Available online: https:\/\/www.chemcraftprog.com\/."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/0009-2614(96)00440-X","article-title":"Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory","volume":"256","author":"Bauernschmitt","year":"1996","journal-title":"Chem. Phys. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"8218","DOI":"10.1063\/1.477483","article-title":"An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules","volume":"109","author":"Stratmann","year":"1998","journal-title":"J. Chem. Phys."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1016\/S0009-2614(03)00782-6","article-title":"Missing Conformers: Comparative Study of Conformational Cooling in Cyanoacetic Acid and Methyl Cyanoacetate Isolated in Low Temperature Inert Gas Matrixes","volume":"374","author":"Reva","year":"2003","journal-title":"Chem. Phys. Lett."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"7499","DOI":"10.1021\/jp900771g","article-title":"Conformational Cooling Dynamics in Matrix-Isolated 1,3-butanediol","volume":"113","author":"Rosado","year":"2009","journal-title":"J. Phys. Chem. A"}],"container-title":["Photochem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2673-7256\/2\/2\/26\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:18:15Z","timestamp":1760138295000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2673-7256\/2\/2\/26"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,25]]},"references-count":42,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2022,6]]}},"alternative-id":["photochem2020026"],"URL":"https:\/\/doi.org\/10.3390\/photochem2020026","relation":{},"ISSN":["2673-7256"],"issn-type":[{"type":"electronic","value":"2673-7256"}],"subject":[],"published":{"date-parts":[[2022,5,25]]}}}