{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T10:33:56Z","timestamp":1789986836746,"version":"4.0.1"},"reference-count":35,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2024,1,27]],"date-time":"2024-01-27T00:00:00Z","timestamp":1706313600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["22066007"],"award-info":[{"award-number":["22066007"]}]},{"name":"National Natural Science Foundation of China","award":["22065009"],"award-info":[{"award-number":["22065009"]}]},{"name":"National Natural Science Foundation of China","award":["ZK[2022]395"],"award-info":[{"award-number":["ZK[2022]395"]}]},{"name":"National Natural Science Foundation of China","award":["ZK[2023]291"],"award-info":[{"award-number":["ZK[2023]291"]}]},{"name":"Guizhou Provincial Natural Science Foundation","award":["22066007"],"award-info":[{"award-number":["22066007"]}]},{"name":"Guizhou Provincial Natural Science Foundation","award":["22065009"],"award-info":[{"award-number":["22065009"]}]},{"name":"Guizhou Provincial Natural Science Foundation","award":["ZK[2022]395"],"award-info":[{"award-number":["ZK[2022]395"]}]},{"name":"Guizhou Provincial Natural Science Foundation","award":["ZK[2023]291"],"award-info":[{"award-number":["ZK[2023]291"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this study, we synthesized a coumarin\u2013hemicyanine-based deep red fluorescent dye that exhibits an intramolecular charge transfer (ICT). The probe had a large Stokes shift of 287 nm and a large molar absorption coefficient (\u03b5 = 7.5 \u00d7 105 L\u00b7mol\u22121\u00b7cm\u22121) and is best described as a deep red luminescent fluorescent probe with \u03bbem = 667 nm. The color of probe W changed significantly when it encountered cyanide ions (CN\u2212). The absorption peak (585 nm) decreased gradually, and the absorption peak (428 nm) increased gradually, so that cyanide (CN\u2212) could be identified by the naked eye. Moreover, an obvious fluorescence change was evident before and after the reaction under irradiation using 365 nm UV light. The maximum emission peak (667 nm) decreased gradually, whilst the emission peak (495 nm) increased gradually, which allowed for the proportional fluorescence detection of cyanide (CN\u2212). Using fluorescence spectrometry, the fluorescent probe W could linearly detect CN\u2212 over the concentration range of 1\u20139 \u03bcM (R2 = 9913, RSD = 0.534) with a detection limit of 0.24 \u03bcM. Using UV-Vis spectrophotometry, the linear detection range for CN\u2212 was found to be 1\u201327 \u03bcM (R2 = 0.99583, RSD = 0.675) with a detection limit of 0.13 \u03bcM. The sensing mechanism was confirmed by 1H NMR spectroscopic titrations, 13C NMR spectroscopy, X-ray crystallographic analysis and HRMS. The recognition and detection of CN\u2212 by probe W was characterized by a rapid response, high selectivity, and high sensitivity. Therefore, this probe provides a convenient, effective and economical method for synthesizing and detecting cyanide efficiently and sensitively.<\/jats:p>","DOI":"10.3390\/molecules29030618","type":"journal-article","created":{"date-parts":[[2024,1,30]],"date-time":"2024-01-30T05:14:32Z","timestamp":1706591672000},"page":"618","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["A Coumarin\u2013Hemicyanine Deep Red Dye with a Large Stokes Shift for the Fluorescence Detection and Naked-Eye Recognition of Cyanide"],"prefix":"10.3390","volume":"29","author":[{"given":"Dongmei","family":"Li","sequence":"first","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Senlin","family":"Peng","sequence":"additional","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xu","family":"Zhou","sequence":"additional","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lingyi","family":"Shen","sequence":"additional","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xianjiong","family":"Yang","sequence":"additional","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hong","family":"Xu","sequence":"additional","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2090-1688","authenticated-orcid":false,"given":"Carl","family":"Redshaw","sequence":"additional","affiliation":[{"name":"Chemistry, School of Natural Sciences, University of Hull, Cottingham Road, Hull HU6 7RX, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chunlin","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9621-4016","authenticated-orcid":false,"given":"Qilong","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Basic Medical Science, Guizhou Medical University, Guiyang 550004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"9614","DOI":"10.1039\/C6CC03761E","article-title":"Anion recognition by oligo-(thio)urea-based receptors","volume":"52","author":"Jia","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1409","DOI":"10.1007\/s10895-021-02771-8","article-title":"Cyanine-based Fluorescent Probe for Cyanide Ion Detection","volume":"31","author":"Gosi","year":"2021","journal-title":"J. Fluoresc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"986","DOI":"10.1016\/j.snb.2015.06.042","article-title":"A \u201cdonor-two-acceptor\u201d sensor for cyanide detection in aqueous solution","volume":"220","author":"Li","year":"2015","journal-title":"Sens. Actuators B Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"537","DOI":"10.1007\/s12039-016-1051-y","article-title":"An interesting spectroscopic method for chromofluorogenic detection of cyanide ion in aqueous solution: Disruption of intramolecular charge transfer (ICT)","volume":"128","author":"Abdolhamid","year":"2016","journal-title":"J. Chem. Sci."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"330","DOI":"10.1016\/j.snb.2016.01.055","article-title":"Highly selective colorimetric\/fluorometric dual-channel sensor for cyanide based on ICT off in aqueous solution","volume":"228","author":"Li","year":"2016","journal-title":"Sens. Actuators B Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1446","DOI":"10.1039\/c2py20022h","article-title":"A new polyfluorene bearing pyridine moieties: A sensitive fluorescent chemosensor for metal ions and cyanide","volume":"3","author":"Lou","year":"2012","journal-title":"Polym. Chem."},{"key":"ref_7","unstructured":"(2007). Standards for Drinking Water Quality (Standard No. GB 5749-2006)."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1039\/B907368J","article-title":"Sensors for the optical detection of cyanide ion","volume":"39","author":"Xu","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1446","DOI":"10.1039\/b205378k","article-title":"Simultaneous determination of cyanide and carbonyls in cyanogenic plants by gas chromatography-electron capture\/photoionization detection","volume":"127","author":"Curtis","year":"2002","journal-title":"Analyst"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/j.saa.2017.05.012","article-title":"A new azine derivative colorimetric and fluorescent dual-channel probe for cyanide detection","volume":"184","author":"Yu","year":"2017","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1021\/ac034713m","article-title":"Subnanomolar cyanide detection at polyphenol oxidase\/clay biosensors","volume":"76","author":"Shan","year":"2004","journal-title":"Anal. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/j.aca.2013.01.029","article-title":"A disposable blood cyanide sensor","volume":"20","author":"Tian","year":"2013","journal-title":"Anal. Chim. Acta."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1021\/ol7025763","article-title":"Fluorescent chemodosimeter for selective detection of cyanide in water","volume":"10","author":"Lee","year":"2008","journal-title":"Org. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"192","DOI":"10.1021\/cr2004103","article-title":"Luminescent chemodosimeters for bioimaging","volume":"113","author":"Yang","year":"2013","journal-title":"Chem. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3406","DOI":"10.1021\/ol101281x","article-title":"Specific Recognition and Sensing of CN\u2212 in Sodium Cyanide Solution","volume":"12","author":"Sukdeb","year":"2010","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1016\/j.jlumin.2015.06.046","article-title":"A turn-on fluorescent sensor for detection of cyanide in aqueous media","volume":"167","author":"Wang","year":"2015","journal-title":"J. Lumin."},{"key":"ref_17","first-page":"20","article-title":"A reactive fluorescence probe based on naphthalene isothiocyanate for Hg+","volume":"50","author":"Chen","year":"2018","journal-title":"J. South China Norm. Univ."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.talanta.2018.03.013","article-title":"A highly selective fluorescent probe for cyanide ion and its detection mechanism from theoretical calculations","volume":"185","author":"Li","year":"2018","journal-title":"Talanta"},{"key":"ref_19","first-page":"731","article-title":"Anion Ratio Fluorescent Molecular Probe Based on Intramolecular Charge Transfer","volume":"27","author":"Liu","year":"2011","journal-title":"J. Inorg. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"10403","DOI":"10.1021\/acs.chemrev.9b00145","article-title":"Coumarin-Based Small-Molecule Fluorescent Chemosensors","volume":"119","author":"Cao","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Cheng, S.Y., Pan, X.H., Shi, M.Y., Su, T., Zhang, C., Zhao, W., and Dong, W. (2020). A coumarin-connected carboxylic indolinium sensor for cyanide detection in absolute aqueous medium and its application in biological cell imaging. Spectrochim. Acta A Mol. Biomol. Spectrosc., 228.","DOI":"10.1016\/j.saa.2019.117710"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1016\/j.snb.2019.05.058","article-title":"A mitochondria-targeted ratiometric fluorescent probe for endogenous cyanide in biological samples","volume":"294","author":"Zhu","year":"2019","journal-title":"Sens. Actuators B Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"923149","DOI":"10.3389\/fchem.2022.923149","article-title":"A Turn-On Fluorescent Chemosensor for Cyanide Ion Detection in Real Water Samples","volume":"10","author":"Shi","year":"2022","journal-title":"Front. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"12843","DOI":"10.1039\/c1cc15721c","article-title":"Ratiometric fluorescence detection of cyanide based on a hybrid coumarin\u2013hemicyanine dye: The large emission shift and the high selectivity","volume":"47","author":"Lv","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"8447","DOI":"10.1021\/jacs.0c02201","article-title":"Light-Driven Expansion of Spiropyran Hydrogels","volume":"142","author":"Li","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1016\/j.snb.2015.01.122","article-title":"A near-infrared fluorescent probe for rapid, colorimetric and ratiometric detection of bisulfite in food, serum, and living cells","volume":"211","author":"Zhang","year":"2015","journal-title":"Sens. Actuators B Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","article-title":"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Crystallogr."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT\u2013Integrated space-group and crystal-structure determination","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. A Found. Adv."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1039\/C8NJ05587D","article-title":"An easy to make chemoreceptor for the selective ratiometric fluorescent detection of cyanide in aqueous solution and in food materials","volume":"43","author":"Kumar","year":"2019","journal-title":"New J. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"10784","DOI":"10.1021\/acsomega.9b01308","article-title":"Determination of Cyanide in Water and Food Samples Using an Efficient Naphthalene-Based Ratiometric Fluorescent Probe","volume":"4","author":"Long","year":"2019","journal-title":"ACS Omega"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1002\/jhet.3113","article-title":"Rapid and Selective Detection of Cyanide Anion by Enhanced Fluorescent Emission and Colorimetric Color Changes at Micromole Levels in Aqueous Medium","volume":"55","author":"Qu","year":"2018","journal-title":"J. Heterocycl. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"131745","DOI":"10.1016\/j.matlet.2022.131745","article-title":"Preparation a novel phenylcarbazole-based fluorescent sensor for the sensitive and selective detection of CN\u2212 in water","volume":"313","author":"Zhang","year":"2022","journal-title":"Mater. Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/j.saa.2016.12.009","article-title":"A new unsymmetrical azine derivative based on coumarin group as dual-modal sensor for CN\u2212 and fluorescent \u201cOFF-ON\u201d for Zn2+","volume":"175","author":"Hu","year":"2017","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/j.saa.2017.03.052","article-title":"A novel dual-channel chemosensor for CN\u2212 using asymmetric double-azine derivatives in aqueous media and its application in bitter almond","volume":"181","author":"Pei","year":"2017","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"771","DOI":"10.1139\/cjc-2017-0163","article-title":"A simple azoquinoline based highly selective colorimetric sensor for CN\u2212 anion in aqueous media","volume":"95","author":"Koc","year":"2017","journal-title":"Can. J. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/3\/618\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T13:50:27Z","timestamp":1760104227000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/3\/618"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,27]]},"references-count":35,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2024,2]]}},"alternative-id":["molecules29030618"],"URL":"https:\/\/doi.org\/10.3390\/molecules29030618","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1,27]]}}}