{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T13:52:08Z","timestamp":1787061128679,"version":"build-2736575974"},"reference-count":41,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2020,8,26]],"date-time":"2020-08-26T00:00:00Z","timestamp":1598400000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>In this study, the synthesis and structure of 4-aminocoumarin derivatives of resorcin[4]arene were investigated. Spectroscopic analysis and quantum mechanical calculations showed that this molecule undertakes a crown-in conformation in chloroform. The conformations of the aminocoumarin derivative of resorcin[4]arene were compared with a hydroxycoumarin derivative of resorcin[4]arene, and the effect of the substituent on the conformational selectivity of the coumarin derivatives of resorcin[4]arene was demonstrated. Both UV-VIS and fluorescence spectroscopy for the coumarin derivative of resorcin[4]arene (3) were performed, and a strong fluorescence quenching of derivative 3 compared to 4-aminocoumarin was observed.<\/jats:p>","DOI":"10.3390\/ijms21176160","type":"journal-article","created":{"date-parts":[[2020,8,26]],"date-time":"2020-08-26T09:05:37Z","timestamp":1598432737000},"page":"6160","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Intramolecular Hydrogen Bond Driven Conformational Selectivity of Coumarin Derivatives of Resorcin[4]arene"],"prefix":"10.3390","volume":"21","author":[{"given":"Anna","family":"Szafraniec","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Pozna\u0144skiego 8, 60-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0227-0034","authenticated-orcid":false,"given":"Waldemar","family":"Iwanek","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, UTP, University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,8,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"10940","DOI":"10.1021\/cr500081p","article-title":"Review: A history of cyclodextrins","volume":"114","author":"Crini","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"7017","DOI":"10.1021\/ja01002a035","article-title":"Cyclic polyethers and their complexes with metal salts","volume":"89","author":"Pedersen","year":"1967","journal-title":"J. Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5022","DOI":"10.1021\/ja711260m","article-title":"Para-Bridged symmetrical pillar[5]arenes: Their Lewis acid catalyzed synthesis and host-guest property","volume":"130","author":"Ogoshi","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7367","DOI":"10.1021\/ja00414a070","article-title":"Cucurbituril","volume":"103","author":"Freeman","year":"1981","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","unstructured":"Gutsche, C.D. (2008). Calixarenes, Royal Society of Chemistry."},{"key":"ref_6","unstructured":"Stoddart, J.F. (1994). Container Molecules and Their Guests, Monographs in Supramolecular Chemistry, The Royal Society of Chemistry."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2663","DOI":"10.1016\/0040-4020(95)00984-1","article-title":"Resorcinarenes","volume":"52","author":"Timmerman","year":"1996","journal-title":"Tetrahedron"},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Neri, P., Sessler, J.L., and Wang, M.X. (2016). Calixarenes and Beyond, Springer International Publishing.","DOI":"10.1007\/978-3-319-31867-7"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1358","DOI":"10.1039\/C7SC05167K","article-title":"High-Affinity and Selective Detection of Pyrophosphate in Water by a Resorcinarene Salt Receptor","volume":"9","author":"Beyeh","year":"2018","journal-title":"Chem. Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2278","DOI":"10.1039\/C2TA01146H","article-title":"Assembling Gold and Platinum Nanoparticles on Resorcinarene Modified Graphene and Their Electrochemical Applications","volume":"1","author":"Zhou","year":"2013","journal-title":"J. Mater. Chem. A"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"10684","DOI":"10.1039\/C6TC04062D","article-title":"Calix[4]Resorcinarene-Based Branched Macromolecules for All-Optical Photorefractive Applications","volume":"4","author":"Liu","year":"2016","journal-title":"J. Mater. Chem. C"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"332","DOI":"10.2174\/1385272824666200211114211","article-title":"Synthesis of New Tetra Triazole Functionalized Calix[4]resorcinarene and Chemosensing of Copper Ions in Aqueous Medium","volume":"24","author":"Qadri","year":"2020","journal-title":"Curr. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1007\/s10847-013-0336-8","article-title":"Application of Resorcinarene Derivatives in Chemical Separations","volume":"78","author":"Li","year":"2014","journal-title":"J. Incl. Phenom. Macrocycl. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1039\/C4CS00153B","article-title":"Self-Assembled Capsules Based on Tetrafunctionalized Calix [4] Resorcinarene Cavitands","volume":"44","author":"Kobayashi","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"931","DOI":"10.1021\/cr960048o","article-title":"Carceplexes and Hemicarceplexes","volume":"99","author":"Jasat","year":"1999","journal-title":"Chem. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Rebek, J. (2016). Hydrogen-Bonded Capsules: Molecular Behavior in Small Spaces, World Scientific Publishing.","DOI":"10.1142\/9605"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1002\/(SICI)1099-0690(199909)1999:9<2257::AID-EJOC2257>3.0.CO;2-H","article-title":"Self-Assembly of 2,8,14,20-Tetraisobutyl-5,11,17,23-tetrahydroxyresorc[4]arene","volume":"9","author":"Gerkensmeier","year":"1999","journal-title":"Eur. J. Org. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"4289","DOI":"10.1016\/S0957-4166(98)00458-3","article-title":"Chiral calixarene derived from resorcinol. Part 4: Diastereoselective closure of the oxazine ring","volume":"9","author":"Iwanek","year":"1998","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"6018","DOI":"10.1021\/acs.joc.6b01099","article-title":"The inverse demand oxa-Diels\u2014Alder reaction of resorcinarenes: An experimental and theoretical analysis of regioselectivity and diastereoselectivity","volume":"81","author":"Wierzbicki","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2516","DOI":"10.1039\/B206188K","article-title":"The synthesis and crystallographic structures of novel bora-oxazino-oxazolidine derivatives of resorcarene","volume":"21","author":"Iwanek","year":"2002","journal-title":"Chem. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2097","DOI":"10.1021\/acs.accounts.5b00152","article-title":"Supramolecular Modeling of Mono-Copper Enzyme Active Sites with Funnel-Complexes","volume":"48","author":"Poul","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Twum, K., Rautiainen, J., Yu, S., Truong, K.-N., Feder, J., Rissanen, K., Puttreddy, R., and Beyeh, N.K. (2020). Host-Guest Interactions of Sodium sulfonate methyleneresorcinarene and Quaternary Ammonium Halides: An Experimental-Computational Analysis of the Guest Inclusion Properties. Cryst. Growth Des.","DOI":"10.1021\/acs.cgd.9b01540"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"13799","DOI":"10.1039\/C5CC05728K","article-title":"Switching of inherent chirality driven by self-assembly","volume":"51","author":"Kwit","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4775","DOI":"10.1002\/chem.200600085","article-title":"Conformational Behavior of Pyrazine-Bridged and Mixed-Bridged Cavitands: A General Model for Solvent Effects on Thermal \u201cVase\u2013Kite\u201d Switching","volume":"12","author":"Roncucci","year":"2006","journal-title":"Chem. Eur. J."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1002\/adfm.200500181","article-title":"Resorcin[4]arene Cavitand-Based Molecular Switches","volume":"16","author":"Azov","year":"2006","journal-title":"Adv. Funct. Mater."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2146","DOI":"10.1002\/1522-2675(20010711)84:7<2146::AID-HLCA2146>3.0.CO;2-K","article-title":"Conformational switching of resorcin[4]arene cavitands by protonation, preliminary communication","volume":"84","author":"Skinner","year":"2001","journal-title":"Helv. Chim. Acta"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2470","DOI":"10.1021\/acs.jpclett.6b01094","article-title":"Paramagnetic Molecular Grippers: The Elements of Six-State Redox Switches","volume":"7","author":"Milic","year":"2016","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1431","DOI":"10.1002\/chem.201704788","article-title":"Photoredox-Switchable Resorcin[4]arene Cavitands: Radical Control of Molecular Gripping Machinery via Hydrogen Bonding","volume":"24","author":"Zalibera","year":"2018","journal-title":"Chem. Eur. J."},{"key":"ref_29","unstructured":"Simpson, J. (2008). Organic Structure Determination Using 2-D NMR Spectroscopy: A Problem-Based Approach, Elsevier."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"12747","DOI":"10.1039\/D0RA00368A","article-title":"Synthesis of a coumarin derivative of resorcin[4]arene with solvent-controlled chirality","volume":"10","author":"Szafraniec","year":"2020","journal-title":"RSC Adv."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1096","DOI":"10.1021\/ol400118t","article-title":"The Missing Member of the Partially O-Alkylated Resorcinarene Family: Synthesis and Conformation of Methyl Tetramethoxy Resorcinarene","volume":"15","author":"Tero","year":"2013","journal-title":"Org. Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3869","DOI":"10.1021\/ol006608u","article-title":"Facile Lewis Acid Catalyzed Synthesis of C4 Symmetric Resorcinarenes","volume":"2","author":"McIldowie","year":"2000","journal-title":"Org. Lett."},{"key":"ref_33","unstructured":"Frisch, M.J., 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, Revision D.01, Gaussian, Inc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1652","DOI":"10.1021\/acs.jctc.8b01176","article-title":"GFN2-xTB an Accurate and Broadly Parametrized Self Consistent Tight-Binding Quantum Chemical Method with Multipole Electrostatics and Density-Dependent Dispersion Contributions","volume":"15","author":"Bannwarth","year":"2019","journal-title":"J. Chem. Theory Comput."},{"key":"ref_35","unstructured":"Grimme, S. (2020, March 16). Semiempirical Extended Tight-Binding Program Package xtb. Available online: https:\/\/github.com\/grimme-lab\/xtb."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2176","DOI":"10.1021\/om100106e","article-title":"NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist","volume":"29","author":"Fulmer","year":"2010","journal-title":"Organometallics"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"10403","DOI":"10.1021\/acs.chemrev.9b00145","article-title":"Correction to coumarin-based small-molecule fluorescent chemosensors","volume":"119","author":"Cao","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2707","DOI":"10.1016\/j.tetlet.2006.02.087","article-title":"New cavitand derivatives bearing four coumarin groups as fluorescent chemosensors for Cu2+ and recognition of dicarboxylates utilizing Cu2+ complex","volume":"47","author":"Jang","year":"2006","journal-title":"Tetrahedron Let."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"16628","DOI":"10.3390\/ijms150916628","article-title":"Deactivation of 6-Aminocoumarin Intramolecular ChargeTransfer Excited State through Hydrogen Bonding","volume":"15","author":"Krystkowiak","year":"2014","journal-title":"Int. J. Mol. Sci."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"117110","DOI":"10.1016\/j.jlumin.2020.117110","article-title":"Theoretical investigation of intermolecular hydrogen bond induces fluorescence quenching phenomenon for Coumarin-1","volume":"221","author":"Li","year":"2020","journal-title":"J. Lumin."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1508","DOI":"10.1016\/j.tet.2005.11.017","article-title":"Synthesis of alkoxymethyl derivatives of resorcinarene via the Mannich reaction catalysed with iminodiacetic acid","volume":"62","author":"Urbaniak","year":"2006","journal-title":"Tetrahedron"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/21\/17\/6160\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:07:08Z","timestamp":1760177228000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/21\/17\/6160"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,8,26]]},"references-count":41,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2020,9]]}},"alternative-id":["ijms21176160"],"URL":"https:\/\/doi.org\/10.3390\/ijms21176160","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,8,26]]}}}