{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,22]],"date-time":"2026-01-22T13:54:50Z","timestamp":1769090090967,"version":"3.49.0"},"reference-count":45,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2019,10,17]],"date-time":"2019-10-17T00:00:00Z","timestamp":1571270400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Sensors"],"abstract":"<jats:p>For efficiently measuring copper (II) ions in the acidic media of white wine, a new chemosensor based on rhodamine B coupled to a tetraazamacrocyclic ring (13aneN4CH2NH2) was designed and synthesized by a one-pot reaction using ethanol as a green solvent. The obtained chemosensor was characterized via NMR, UV and fluorescent spectra. It was marked with no color emission under neutral pH conditions, with a pink color emission under acidic conditions, and a magenta color emission under acidic conditions where copper (II) ions were present. The sensitivity towards copper (II) ions was tested and verified over Ca2+, Ag+, Zn2+, Mg2+, Co2+, Ni2+, Fe2+, Pb2+, Cd2+, Fe3+, and Mn2+, with a detection limit of 4.38     \u00d7     10\u22128 M in the fluorescence spectrum.<\/jats:p>","DOI":"10.3390\/s19204514","type":"journal-article","created":{"date-parts":[[2019,10,17]],"date-time":"2019-10-17T11:07:59Z","timestamp":1571310479000},"page":"4514","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine"],"prefix":"10.3390","volume":"19","author":[{"given":"Nour","family":"Doumani","sequence":"first","affiliation":[{"name":"UMR PAM Proc\u00e9d\u00e9s Alimentaires et Microbiologiques, Universit\u00e9 de Bourgogne Franche-Comt\u00e9\/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, France"},{"name":"D\u00e9partement de Chimie et de Biochimie, Facult\u00e9 des Sciences II, Universit\u00e9 Libanaise, Jdeideth El Matn, Fanar 90656, Lebanon"},{"name":"D\u00e9partement des Sciences de la Vie et de la Terre - Nutrition, Facult\u00e9 des Sciences II, Universit\u00e9 Libanaise,  Jdeideth El Matn, Fanar 90656, Lebanon"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0208-858X","authenticated-orcid":false,"given":"Elias","family":"Bou-Maroun","sequence":"additional","affiliation":[{"name":"UMR PAM Proc\u00e9d\u00e9s Alimentaires et Microbiologiques, Universit\u00e9 de Bourgogne Franche-Comt\u00e9\/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, France"}]},{"given":"Jacqueline","family":"Maalouly","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie et de Biochimie, Facult\u00e9 des Sciences II, Universit\u00e9 Libanaise, Jdeideth El Matn, Fanar 90656, Lebanon"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4396-2958","authenticated-orcid":false,"given":"Maya","family":"Tueni","sequence":"additional","affiliation":[{"name":"D\u00e9partement des Sciences de la Vie et de la Terre - Nutrition, Facult\u00e9 des Sciences II, Universit\u00e9 Libanaise,  Jdeideth El Matn, Fanar 90656, Lebanon"}]},{"given":"Adrien","family":"Dubois","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire de l\u2019Universit\u00e9 de Bourgogne, UMR 5260, CNRS-12 Universit\u00e9 de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon, France"}]},{"given":"Claire","family":"Bernhard","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire de l\u2019Universit\u00e9 de Bourgogne, UMR 5260, CNRS-12 Universit\u00e9 de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon, France"}]},{"given":"Franck","family":"Denat","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire de l\u2019Universit\u00e9 de Bourgogne, UMR 5260, CNRS-12 Universit\u00e9 de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon, France"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6998-8569","authenticated-orcid":false,"given":"Philippe","family":"Cayot","sequence":"additional","affiliation":[{"name":"UMR PAM Proc\u00e9d\u00e9s Alimentaires et Microbiologiques, Universit\u00e9 de Bourgogne Franche-Comt\u00e9\/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, France"}]},{"given":"Nicolas","family":"Sok","sequence":"additional","affiliation":[{"name":"UMR PAM Proc\u00e9d\u00e9s Alimentaires et Microbiologiques, Universit\u00e9 de Bourgogne Franche-Comt\u00e9\/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, France"}]}],"member":"1968","published-online":{"date-parts":[[2019,10,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"886","DOI":"10.3945\/ajcn.115.117994","article-title":"Calcium intake and mortality from all causes, cancer, and cardiovascular disease: The Cancer Prevention Study II Nutrition Cohort","volume":"103","author":"Yang","year":"2016","journal-title":"Am. J. Clin. Nutr."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/S0269-7491(00)00067-1","article-title":"Evaluation of copper availability to plants in copper-contaminated vineyard soils","volume":"111","author":"Brun","year":"2001","journal-title":"Environ. Pollut."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1111\/j.1744-7348.1943.tb06719.x","article-title":"Studies upon the Copper Fungicides.: VI. The Solution of Copper from Bordeaux and Burgundy Mixtures","volume":"30","author":"Wain","year":"1943","journal-title":"Ann. Appl. Biol."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Dias, A.A., Fernandes, J.M.C., Sousa, R.M.O.F., Pinto, P.A., Amaral, C., Sampaio, A., and Bezerra, R.M.F. (2018). Fungal Conversion and Valorization of Winery Wastes. Mycoremediation and Environmental Sustainability, Springer.","DOI":"10.1007\/978-3-319-77386-5_9"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Tromp, A., and de Klerk, C.A. (1988). Effect of Copperoxychloride on the Fermentation of Must and on Wine Quality. S. Afr. J. Enol. Vitic., 9.","DOI":"10.21548\/9-1-2307"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/S0003-2670(00)00830-8","article-title":"Determination of total copper in white wine by stripping potentiometry utilising medium exchange","volume":"413","author":"Clark","year":"2000","journal-title":"Anal. Chim. Acta"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1093\/clinchem\/35.4.552","article-title":"Sensitive, Direct Colorimetric Assay for Copper in Serum","volume":"35","author":"Abe","year":"1989","journal-title":"Clin. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"606","DOI":"10.1016\/j.dyepig.2012.05.025","article-title":"Design and Synthesis of Rhodamine Based Chemosensors for the Detection of Fe3+ Ions","volume":"95","author":"Chereddy","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1860","DOI":"10.1021\/ac00083a014","article-title":"Simultaneous Immunoassay Using Electrochemical Detection of Metal Ion Labels","volume":"66","author":"Hayes","year":"1994","journal-title":"Anal. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1248\/bpb.24.10","article-title":"Iron Concentrations in Human Dermis Assessed by Microdialysis Associated with Atomic Absorption Spectrometry","volume":"24","author":"Robin","year":"2001","journal-title":"Boil. Pharm. Bull."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"9097","DOI":"10.3390\/s150409097","article-title":"Highly Sensitive and Selective Colorimetric and Off-On Fluorescent Reversible Chemosensors for Al3+ Based on the Rhodamine Fluorophore","volume":"15","author":"Mergu","year":"2015","journal-title":"Sensors"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2810","DOI":"10.1039\/b502212f","article-title":"Fluorescence quenching amplification in silica nanosensors for metal ions","volume":"15","author":"Montalti","year":"2005","journal-title":"J. Mater. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"4400","DOI":"10.1039\/C4CS00346B","article-title":"Synthetic fluorescent probes for studying copper in biological systems","volume":"44","author":"Cotruvo","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.dyepig.2009.11.007","article-title":"A rhodamine-based dual chemosensor for the visual detection of copper and the ratiometric fluorescent detection of vanadium","volume":"86","author":"Huo","year":"2010","journal-title":"Dyes Pigment."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"406","DOI":"10.1021\/ol203186b","article-title":"Highly Selective Fluorescence Turn-on Chemodosimeter Based on Rhodamine for Nanomolar Detection of Copper Ions","volume":"14","author":"Kumar","year":"2012","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1717","DOI":"10.1016\/j.talanta.2007.02.002","article-title":"A new fluorescent probe of rhodamine B derivative for the detection of copper ion","volume":"72","author":"Mei","year":"2007","journal-title":"Talanta"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"482","DOI":"10.1016\/j.snb.2012.07.035","article-title":"Highly Sensitive and Selective Rhodamine Schiff Base \u201coff-on\u201d Chemosensors for Cu2+ Imaging in Living Cells","volume":"176","author":"Yang","year":"2013","journal-title":"Sens. Actuators B"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"130","DOI":"10.5395\/rde.2016.41.2.130","article-title":"The effect of red and white wine on color changes of nanofilled and nanohybrid resin composites","volume":"41","author":"Tanthanuch","year":"2016","journal-title":"Restor. Dent. Endod."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1465","DOI":"10.1039\/b802497a","article-title":"A new trend in rhodamine-based chemosensors: Application of spirolactam ring-opening to sensing ions","volume":"37","author":"Lee","year":"2008","journal-title":"Chem. Soc. Rev."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1549","DOI":"10.1021\/ol060001h","article-title":"A New Rhodamine-Based Chemosensor Exhibiting Selective FeIII-Amplified Fluorescence","volume":"8","author":"Xiang","year":"2006","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1143","DOI":"10.1021\/jo202056t","article-title":"Three Rhodamine-Based \u201cOff\u2013On\u201d Chemosensors with High Selectivity and Sensitivity for Fe3+ Imaging in Living Cells","volume":"77","author":"Yang","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"5455","DOI":"10.1016\/j.tetlet.2007.05.171","article-title":"A new rhodamine-based fluorescent chemosensor for transition metal cations synthesized by one-step facile condensation","volume":"48","author":"Zhang","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1016\/j.snb.2008.10.044","article-title":"A rhodamine-based chromogenic and fluorescent chemosensor for copper ion in aqueous media","volume":"135","author":"Zhao","year":"2009","journal-title":"Sens. Actuators B Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2008","DOI":"10.1021\/ja808611d","article-title":"Coumarin-Derived Cu2+ -Selective Fluorescence Sensor: Synthesis, Mechanisms, and Applications in Living Cells","volume":"131","author":"Jung","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/j.snb.2014.03.064","article-title":"A Rhodamine-Based Colorimetric and Reversible Fluorescent Chemosensor for Selectively Detection of Cu2+ and Hg2+ Ions","volume":"199","author":"Yang","year":"2014","journal-title":"Sens. Actuators B"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Denat, F., Diaz-Fernandez, Y.A., Pallavicini, P., Pasotti, L., Rousselin, Y., and Sok, N. (2009). The Cu(II) complex of a C-lipophilized 13aneN4 macrocycle with an additional protonable amino group as micellar anion receptor. Dalton Trans., 6751\u20136758.","DOI":"10.1039\/b907289f"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3944","DOI":"10.1039\/c4ob00131a","article-title":"Development of a New Rhodamine-Based FRET Platform and Its Application as a Cu2+ Probe","volume":"12","author":"Guan","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/0143-7208(94)87009-8","article-title":"Ionization and Tautomerism of Fluorescein, Rhodamine B, N, N-Diethylrhodol and Related Dyes in Mixed and Nonaqueous Solvents","volume":"24","author":"Kukhtik","year":"1994","journal-title":"Dyes Pigm."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1039\/a802897d","article-title":"Detection of nitric oxide and nitrite by using a Rhodamine-type fluorescent indicator","volume":"35","author":"Rieth","year":"1998","journal-title":"Anal. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1688","DOI":"10.1002\/ejoc.200901183","article-title":"Efficient Synthesis of NewC-Functionalized Macrocyclic Polyamines","volume":"2010","author":"Rousselin","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"452","DOI":"10.1016\/0009-2614(88)85007-3","article-title":"Structural relaxation of rhodamine dyes with different N-substitution patterns: A study of fluorescence decay times and quantum yields","volume":"147","author":"Vogel","year":"1988","journal-title":"Chem. Phys. Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"24891","DOI":"10.1039\/c3ra43675f","article-title":"A reversible Hg(ii)-selective fluorescent chemosensor based on a thioether linked bis-rhodamine","volume":"3","author":"Zhang","year":"2013","journal-title":"RSC Adv."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"5106","DOI":"10.1002\/ejic.201600749","article-title":"An Off-On-Off Fluorescent Sensor for PH Windows Based on the 13aneN4-Zn2+ System","volume":"2016","author":"Amendola","year":"2016","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Kodama, M., and Kimura, E. (1977). Equilibria and Kinetics of Complex Formation between Zinc (II), Lead (II), and Cadmium (II), and 12-, 13-, 14-, and 15-Membered Macrocyclic Tetra-Amines. Dalton Trans., 2269\u20132276.","DOI":"10.1039\/dt9770002269"},{"key":"ref_35","unstructured":"ANSES_CIQUAL (2018, March 08). Copper (mg\/100g) content in French food. Available online: https:\/\/ciqual.anses.fr\/#\/constituants\/10290\/copper-(mg-100g)."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"858","DOI":"10.1897\/04-671R.1","article-title":"Ambient copper concentrations in agricultural and natural European soils: An overview","volume":"25","author":"Heijerick","year":"2006","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1016\/j.snb.2015.12.037","article-title":"Semicarbazide-based naphthalimide as a highly selective and sensitive colorimetric and \u201cturn-on\u201d fluorescent chemodosimeter for Cu2+","volume":"227","author":"Hu","year":"2016","journal-title":"Sens. Actuators B Chem."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Cheng, D., Liu, X., Yang, H., Zhang, T., Han, A., and Zang, L. (2017). A Cu2+ Selective Probe Based on Phenanthro-Imidazole Derivative. Sensors, 17.","DOI":"10.3390\/s17010035"},{"key":"ref_39","first-page":"28","article-title":"Ratiometric and selective fluorescent chemodosimeter for Cu(II) by Cu(II)-induced oxidation","volume":"23","author":"Xiang","year":"2008","journal-title":"J. Lumin."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1987","DOI":"10.1016\/j.jlumin.2012.03.039","article-title":"Fluorescence quenching of a rhodamine derivative: Selectively sensing Cu2+ in acidic aqueous media","volume":"132","author":"Ding","year":"2012","journal-title":"J. Lumin."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"21","DOI":"10.4103\/2229-5186.79345","article-title":"Methods for the determination of limit of detection and limit of quantitation of the analytical methods","volume":"2","author":"Shrivastava","year":"2011","journal-title":"Chronicles Young Sci."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1016\/j.jlumin.2013.08.023","article-title":"Simple and sensitive detection method for diprophylline using glutathione-capped CdTe quantum dots as fluorescence probes","volume":"145","author":"Ying","year":"2014","journal-title":"J. Lumin."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"172","DOI":"10.1016\/j.jclepro.2015.04.006","article-title":"Improving environmental performances in wine production by a life cycle assessment analysis","volume":"111","author":"Iannone","year":"2016","journal-title":"J. Clean. Prod."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2564","DOI":"10.1021\/jf1043585","article-title":"Evolution of 3-Mercaptohexanol, Hydrogen Sulfide, and Methyl Mercaptan during Bottle Storage of Sauvignon blanc Wines. Effect of Glutathione, Copper, Oxygen Exposure, and Closure-Derived Oxygen","volume":"59","author":"Ugliano","year":"2011","journal-title":"J. Agric. Food Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"12385","DOI":"10.1021\/jf403422x","article-title":"Effects of Five Metals on the Evolution of Hydrogen Sulfide, Methanethiol, and Dimethyl Sulfide during Anaerobic Storage of Chardonnay and Shiraz Wines","volume":"61","author":"Viviers","year":"2013","journal-title":"J. Agric. Food Chem."}],"container-title":["Sensors"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8220\/19\/20\/4514\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:27:14Z","timestamp":1760189234000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8220\/19\/20\/4514"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,10,17]]},"references-count":45,"journal-issue":{"issue":"20","published-online":{"date-parts":[[2019,10]]}},"alternative-id":["s19204514"],"URL":"https:\/\/doi.org\/10.3390\/s19204514","relation":{},"ISSN":["1424-8220"],"issn-type":[{"value":"1424-8220","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,10,17]]}}}