{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,31]],"date-time":"2026-01-31T17:28:11Z","timestamp":1769880491495,"version":"3.49.0"},"reference-count":30,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2023,1,30]],"date-time":"2023-01-30T00:00:00Z","timestamp":1675036800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004281","name":"National Science Centre, Poland","doi-asserted-by":"publisher","award":["2022\/06\/X\/ST4\/00581"],"award-info":[{"award-number":["2022\/06\/X\/ST4\/00581"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>One of the most basic properties of chemical compounds is structural symmetry or asymmetry. This property can be considered at different levels of structural organization. The physical, chemical, biological, and technological properties of organic compounds depend on their chemical structure and are systematically related to it. The presented paper is focused on the synthesis and study of the spectroscopic properties of selected photoinitiators from the acrylate and methacrylate derivatives of 2-(benzothiazolylthio)ethyl. The indicated compounds can find potential application in medicine. The 2-(benzothiazolylthio)ethyl acrylate and methacrylate derivatives were characterized using infrared spectroscopy (IR) and nuclear magnetic resonance (NMR) spectroscopy. Their spectroscopic properties were determined on the basis of UV\u2013Vis spectra. The calculated DFT energies and Frontier Molecular Orbitals calculations of the studied compounds were proved to be consistent with the experimental observations. The results have showed that the introduction of the ethoxy substituent increases the reactivity of the compounds and results in the slight bathochromic shift (~19 nm) of the absorption spectra maxima.<\/jats:p>","DOI":"10.3390\/sym15020370","type":"journal-article","created":{"date-parts":[[2023,1,30]],"date-time":"2023-01-30T08:28:23Z","timestamp":1675067303000},"page":"370","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and Spectroscopic Properties of Selected Acrylic and Methacrylic Derivatives of 2-Mercaptobenzothiazole"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9375-5642","authenticated-orcid":false,"given":"Janina","family":"Kabatc-Borcz","sequence":"first","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7268-4956","authenticated-orcid":false,"given":"Przemys\u0142aw","family":"Czele\u0144","sequence":"additional","affiliation":[{"name":"Department of Physical Chemistry, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Kurpi\u0144skiego 5, 85-096 Bydgoszcz, Poland"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7286-2692","authenticated-orcid":false,"given":"Agnieszka","family":"Skotnicka","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1021\/acs.chemmater.2c02315","article-title":"Versatile Poly(3,4-ethylenedioxythiophene) Polyelectrolytes for Bioelectronics by Incorporation of an Activated Ester","volume":"35","author":"Tropp","year":"2022","journal-title":"Chem. Mater."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"440","DOI":"10.1021\/acs.chemmater.1c03974","article-title":"Guanidinium Fluorooxoborates as Efficient Metal-free Short-Wavelength Nonlinear Optical Crystals","volume":"34","author":"Jin","year":"2022","journal-title":"Chem. Mater."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1021\/bk-2018-1296.ch016","article-title":"Polymeric Nanoparticles Explored for Drug-Delivery Applications","volume":"1296","author":"Asem","year":"2018","journal-title":"ACS Symp. Ser."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"36837","DOI":"10.1021\/acsami.0c07090","article-title":"Hierarchical Surface Architecture of Hemodialysis Membranes for Eliminating Homocysteine Based on the Multifunctional Role of Pyridoxal 5\u2032-phosphate","volume":"12","author":"Jiang","year":"2020","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"4318","DOI":"10.1021\/acs.biomac.2c00775","article-title":"Anti-Fouling Surfaces for Extracorporeal Membrane Oxygenation by Surface Grafting of Hydrophilic Sulfoxide Polymers","volume":"23","author":"Zhang","year":"2022","journal-title":"Biomacromolecules"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"19736","DOI":"10.1021\/acsami.7b06899","article-title":"Prevention of bacterial colonization on catheters by a one-step coating process involving an antibiofouling polymer in water","volume":"9","author":"Keum","year":"2017","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3957","DOI":"10.1021\/acs.biomac.0c01082","article-title":"Advancing Toward 3D Printing of Bioresorbable Shape Memory Polymer Stents","volume":"21","author":"Yeazel","year":"2020","journal-title":"Biomacromolecules"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"12375","DOI":"10.1021\/acsnano.1c04499","article-title":"Multifunctional 3D-Printed Wound Dressings","volume":"15","author":"Alizadehgiashi","year":"2021","journal-title":"ACS Nano"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3154","DOI":"10.1021\/acsbiomaterials.0c00104","article-title":"Biomaterial-Based Scaffolds as Antibacterial Suture Materials","volume":"6","author":"Fan","year":"2020","journal-title":"ACS Biomater. Sci. Eng."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1021\/acsapm.1c01733","article-title":"Poly(propylene fumarate)-Based Adhesives with a Transformable Adhesion Force for Suture-Free Fixation of Soft Tissue Wounds","volume":"4","author":"Guan","year":"2022","journal-title":"ACS Appl. Polym. Mater."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3487","DOI":"10.1016\/S0142-9612(02)00070-4","article-title":"PVDF as a new polymer for the construction of surgical meshes","volume":"23","author":"Klinge","year":"2002","journal-title":"Biomaterials"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1016\/B978-0-444-53349-4.00230-2","article-title":"Polymeric Implants","volume":"9","author":"Ratner","year":"2012","journal-title":"Polym. Sci. A Compr. Ref."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.mser.2010.05.002","article-title":"Polymers in modern ophthalmic implants\u2014Historical background and recent advances","volume":"69","author":"Bozukova","year":"2010","journal-title":"Mater. Sci. Eng. R Rep."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"402","DOI":"10.1177\/0022034510381263","article-title":"Recent advances and developments in composite dental restorative materials","volume":"90","author":"Cramer","year":"2011","journal-title":"J. Dent. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1016\/j.bsbt.2015.08.002","article-title":"Applications of synthetic polymers in clinical medicine","volume":"1","author":"Maitz","year":"2015","journal-title":"Biosurf. Biotribol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3055","DOI":"10.1021\/bm9006997","article-title":"Foldable antibacterial acrylic intraocular lenses of high refractive index","volume":"10","author":"Parra","year":"2009","journal-title":"Biomacromolecules"},{"key":"ref_17","unstructured":"Chisholm, B.J., and Pickett, J.E. (2006). Method of Making a High Refractive Index Optical Management Coating and the Coating. (7,045,558 B2), U.S. Patent."},{"key":"ref_18","unstructured":"Cracium, L., Polishchuk, O., Schriver, G.W., and Hainz, R. (2008). High Refractive Index Monomers, Compositions and Uses Thereof. (2008\/0200582 A1), U.S. Patent."},{"key":"ref_19","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"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density-functional thermochemistry. III. The role of exact exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.synthmet.2014.05.015","article-title":"Evaluation of various density functionals for predicting the electrophosphorescent host HOMO, LUMO and triplet energies","volume":"195","author":"Ong","year":"2014","journal-title":"Synth. Met."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2193","DOI":"10.1063\/1.455064","article-title":"A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements","volume":"89","author":"Petersson","year":"1988","journal-title":"J. Chem. Phys."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"6081","DOI":"10.1063\/1.460447","article-title":"A complete basis set model chemistry. II. Open-shell systems and the total energies of the first-row atoms","volume":"94","author":"Petersson","year":"1991","journal-title":"J. Chem. Phys."},{"key":"ref_24","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2017, December 07). Gaussian 09, Revision A.02. Available online: http:\/\/gaussian.com\/g09citation\/."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1186\/1758-2946-4-17","article-title":"Avogadro: An advanced semantic chemical editor, visualization, and analysis platform","volume":"4","author":"Hanwell","year":"2012","journal-title":"J. Cheminform."},{"key":"ref_26","unstructured":"Hioki, Y., Shibata, M., Otani, T., Ichinosawa, A., Uehara, H., Sumiya, N., and Teruda, T. (2017). (Meth)acrylate Compound and Polymerizable Composition. (JP2017014213A), Patent."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1016\/j.saa.2013.12.106","article-title":"Molecular structure, Mulliken charge, frontier molecular orbital and first hyperpolarizability analysis on 2-nitroaniline and 4-methoxy-2-nitroaniline using density functional theory","volume":"124","author":"Azhagiri","year":"2014","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"133807","DOI":"10.1016\/j.molstruc.2022.133807","article-title":"Spectroscopic investigation and density functional theory prediction of first and second order hyperpolarizabilities of 1-(4-bromophenyl)-3-(2,4-dichlorophenyl)-prop-2-en-1-one","volume":"1269","author":"Singh","year":"2022","journal-title":"J. Mol. Struct."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Rauk, A. (2001). Orbital Interaction Theory of Organic Chemistry, Wiley-Interscience. [2nd ed.].","DOI":"10.1002\/0471220418"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Streitwieser, A.J. (1961). Molecular Orbital Theory for Organic Chemists, Wiley.","DOI":"10.1149\/1.2425396"}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/15\/2\/370\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:20:13Z","timestamp":1760120413000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/15\/2\/370"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,30]]},"references-count":30,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["sym15020370"],"URL":"https:\/\/doi.org\/10.3390\/sym15020370","relation":{},"ISSN":["2073-8994"],"issn-type":[{"value":"2073-8994","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,30]]}}}