{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T04:26:36Z","timestamp":1760243196281,"version":"build-2065373602"},"reference-count":35,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2015,12,19]],"date-time":"2015-12-19T00:00:00Z","timestamp":1450483200000},"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>We have synthesized two novel fluorescent 3-(4-diethylaminocinnamoyl) coumarins that exhibit fluorescence quenching upon exposure to a nerve agent simulant, diethylchlorophosphate (DCP), providing a basis for rapid and sensitive DCP chemosensing. Furthermore, these coumarin derivatives display two-photon fluorescence upon illumination with near-infrared laser pulses and their two-photon (TP) absorption cross-section was evaluated. The potential for TP bio-imaging of these compounds was investigated by their cellular uptake in HeLa cells by TP confocal microscopy.<\/jats:p>","DOI":"10.3390\/s151229902","type":"journal-article","created":{"date-parts":[[2015,12,21]],"date-time":"2015-12-21T10:43:59Z","timestamp":1450694639000},"page":"31987-31998","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Synthesis and Sensing Applications of Fluorescent 3-Cinnamoyl Coumarins"],"prefix":"10.3390","volume":"15","author":[{"given":"Preeti","family":"Yadav","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Delhi, Delhi 110007, India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hardeep","family":"Gill","sequence":"additional","affiliation":[{"name":"Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA 01854, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karam","family":"Chand","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Delhi, Delhi 110007, India"},{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. 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Ther."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1016\/S0196-0644(05)81036-4","article-title":"Chemical warfare agents: II. Nerve agents","volume":"21","author":"Sidell","year":"1992","journal-title":"Ann. Emerg. Med."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1021\/ac60122a029","article-title":"Detection and estimation of nerve gases by fluorescence reaction","volume":"29","author":"Gehauf","year":"1957","journal-title":"Anal. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5345","DOI":"10.1021\/cr100193y","article-title":"Destruction and detection of chemical warfare agents","volume":"111","author":"Kim","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3420","DOI":"10.1021\/ja029265z","article-title":"Fluorescent detection of chemical warfare agents: functional group specific ratiometric chemosensors","volume":"125","author":"Zhang","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4500","DOI":"10.1021\/ja057449i","article-title":"Fluorescent sensors for organophosphorous nerve agent mimics","volume":"128","author":"Dale","year":"2006","journal-title":"Jr. J. Am. Chem. Soc."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Wallace, K.J., Fagbemi, R.I., Folmer-Andersen, F.J., Morey, J., Lynch, V.M., and Anslyn, E.V. (2006). Detection of Chemical warfare simulants by phosphorylation of a coumarin oximate. Chem. Commun., 3886\u20133888.","DOI":"10.1039\/b609861d"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"383","DOI":"10.1016\/j.talanta.2005.01.043","article-title":"Rapid fluorophosphates nerve agent detection with lanthanides","volume":"67","author":"Menzel","year":"2005","journal-title":"Talanta"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"7850","DOI":"10.1002\/anie.200902820","article-title":"Hydroxy oximes as organophosphorus nerve agent sensor","volume":"48","author":"Dale","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3224","DOI":"10.1039\/c2an35428d","article-title":"Fluorogenic and chromogenic probe for rapid detection of a nerve agent simulant DCP","volume":"137","author":"Wu","year":"2012","journal-title":"Analyst"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"6931","DOI":"10.1002\/chem.201100602","article-title":"Chromogenic, specific detection of the Nerve-Agent Mimic DCNP (a Tabun Mimic)","volume":"17","author":"Royo","year":"2011","journal-title":"Chem. Eur. J."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Costero, A.M., Gil, S., Parra, M., Mancini, P.M.E., Mart\u00ednez-M\u00e1nez, R., Sancen\u00f3n, F., and Royo, S. (2008). Chromogenic detection of nerve agent mimics. Chem. Commun.","DOI":"10.1039\/b811247a"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3059","DOI":"10.1021\/cr030037c","article-title":"Coumarins in polymers: From light harvesting to photo-cross-linkable tissue scaffolds","volume":"104","author":"Trenor","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1316","DOI":"10.3390\/12071316","article-title":"Design and synthesis of a coumarin-based acidichromic colorant","volume":"12","author":"Lin","year":"2007","journal-title":"Molecules"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"5808","DOI":"10.1016\/j.tetlet.2009.07.141","article-title":"New coumarin-based sensor molecule for magnesium and calcium ions","volume":"50","author":"Suresh","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"13447","DOI":"10.1021\/ja072432g","article-title":"Development of an Iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc","volume":"129","author":"Komatsu","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2252","DOI":"10.1021\/ic702388z","article-title":"A coumarin-derived fluorescence probe selective for magnesium","volume":"47","author":"Ray","year":"2008","journal-title":"Inorg. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Lim, N.C., and Bruckner, C. (2004). DPA-substituted coumarins as chemosensors for Zinc (II): Modulation of the chemosensory characteristics by variation of the position of the chelate on the coumarin. Chem. Commun., 1094\u20131095.","DOI":"10.1039\/B403448A"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"8721","DOI":"10.1016\/j.tetlet.2004.09.133","article-title":"An indicator displacement system for fluorescent detection of phosphate oxyanions under physiological conditions","volume":"45","author":"Hanshaw","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1126\/science.2321027","article-title":"Two-photon laser scanning fluorescence microscopy","volume":"248","author":"Denk","year":"1990","journal-title":"Science"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1146\/annurev.bioeng.2.1.399","article-title":"Two-photon excitation fluorescence microscopy","volume":"2","author":"So","year":"2000","journal-title":"Annu. Rev. Biomed. Eng."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1017\/S0033583505004129","article-title":"Two-photon fluorescence excitation and related techniques in biological microscopy","volume":"38","author":"Diaspro","year":"2005","journal-title":"Q. Rev. Biophys."},{"key":"ref_23","first-page":"881","article-title":"Two-photon fluorescence microscopy: Basic principles, advantages and risks","volume":"2","author":"Mulligan","year":"2007","journal-title":"Mod. Res. Educ. Top. Microsc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1016\/j.dyepig.2006.01.020","article-title":"Coumarin derivatives with enhanced Two-photon absorption cross sections","volume":"74","author":"Li","year":"2007","journal-title":"Dyes Pigm."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5288","DOI":"10.1021\/jm400025g","article-title":"Synthesis and in vitro photocytotoxicity of coumarin derivatives for one- and two-photon excited photodynamic therapy","volume":"56","author":"Zou","year":"2013","journal-title":"J. Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1139\/cjc-2013-0053","article-title":"Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl- and pyranochromen-2-one derivatives","volume":"91","author":"Chand","year":"2013","journal-title":"Can. J. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.jphotochem.2014.02.005","article-title":"Synthesis of two-photon active cinnamoyl coumarins for high-contrast imaging of cancer cells and their photophysical characterization","volume":"280","author":"Yadav","year":"2014","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"7352","DOI":"10.1364\/AO.37.007352","article-title":"Two-Photon Fluorescence Excitation Cross Sections of Biomolecular Probes from 690 to 960 nm","volume":"37","author":"Albota","year":"1998","journal-title":"Appl. Opt."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1021\/jo01355a010","article-title":"Synthesis of Some 4-hydroxycoumarin derivatives","volume":"22","author":"Desai","year":"1957","journal-title":"J. Org. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2345","DOI":"10.1071\/CH9682345","article-title":"Studies in 4-hydroxy coumarins","volume":"21","author":"Dholakia","year":"1968","journal-title":"Aust. J. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1016\/0022-2313(82)90045-X","article-title":"Fluorescence quantum yields of some rhodamine dyes","volume":"27","author":"Kubin","year":"1982","journal-title":"J. Lumin."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"188","DOI":"10.1016\/j.jphotochem.2009.06.007","article-title":"Solvent effect on two-photon absorption and fluorescence of rhodamine dyes","volume":"206","author":"Nag","year":"2009","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1002\/cphc.200700397","article-title":"Two-photon absorption cross-sections of reference dyes: A critical examination","volume":"9","author":"Jha","year":"2008","journal-title":"Chem. Phys. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1330","DOI":"10.1021\/am405430t","article-title":"Conjugated poly(fluorene-quinoxaline) for fluorescence imaging and chemical detection of nerve agents with its paper-based strip","volume":"6","author":"Jo","year":"2014","journal-title":"Appl. Mater. Interfac."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2833","DOI":"10.1016\/j.tet.2011.02.041","article-title":"Synthesis, characterization, and evaluation of rhodamine based sensors for nerve gas mimics","volume":"67","author":"Weerasinghe","year":"2011","journal-title":"Tetrahedron"}],"container-title":["Sensors"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8220\/15\/12\/29902\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T20:54:24Z","timestamp":1760216064000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8220\/15\/12\/29902"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,12,19]]},"references-count":35,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2015,12]]}},"alternative-id":["s151229902"],"URL":"https:\/\/doi.org\/10.3390\/s151229902","relation":{},"ISSN":["1424-8220"],"issn-type":[{"type":"electronic","value":"1424-8220"}],"subject":[],"published":{"date-parts":[[2015,12,19]]}}}