{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T05:23:27Z","timestamp":1777440207443,"version":"3.51.4"},"reference-count":43,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2018,4,25]],"date-time":"2018-04-25T00:00:00Z","timestamp":1524614400000},"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>In the present work, we systematically investigate the sensing abilities of two recently literature-reported two-photon fluorescent NO probes, i.e., the o-phenylenediamine derivative of Nile Red and the p-phenylenediamine derivative of coumarin. The recognition mechanisms of these probes are studied by using the molecular orbital classifying method, which demonstrates the photoinduced electron transfer process. In addition, we have designed two new probes by swapping receptor units present on fluorophores, i.e., the p-phenylenediamine derivative of Nile Red and the o-phenylenediamine derivative of coumarin. However, it illustrates that only the latter has ability to function as off-on typed fluorescent probe for NO. More importantly, calculations on the two-photon absorption properties of the probes demonstrate that both receptor derivatives of coumarin possess larger TPA cross-sections than Nile Red derivatives, which makes a better two photon fluorescent probe. Our theoretical investigations reveal that the underlying mechanism satisfactorily explain the experimental results, providing a theoretical basis on the structure-property relationships which is beneficial to developing new two-photon fluorescent probes for NO.<\/jats:p>","DOI":"10.3390\/s18051324","type":"journal-article","created":{"date-parts":[[2018,4,25]],"date-time":"2018-04-25T03:22:45Z","timestamp":1524626565000},"page":"1324","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Theoretical Design of a Two-Photon Fluorescent Probe for Nitric Oxide with Enhanced Emission Induced by Photoninduced Electron Transfer"],"prefix":"10.3390","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7554-3868","authenticated-orcid":false,"given":"Yujin","family":"Zhang","sequence":"first","affiliation":[{"name":"School of Science, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, China"}]},{"given":"Jiancai","family":"Leng","sequence":"additional","affiliation":[{"name":"School of Science, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, China"}]},{"given":"Wei","family":"Hu","sequence":"additional","affiliation":[{"name":"Hefei National Laboratory for Physical Sciences at the Microscale, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China"}]}],"member":"1968","published-online":{"date-parts":[[2018,4,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.aca.2013.09.019","article-title":"Novel b,o-chelated fluorescent probe for nitric oxide imaging in raw 264.7 macrophages and onion tissues","volume":"800","author":"Chen","year":"2013","journal-title":"Anal. Chim. Acta"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1554","DOI":"10.1016\/j.cclet.2016.06.016","article-title":"A 1,8-naphthalimide-derived turn-on fluorescent probe for imaging lysosomal nitric oxide in living cells","volume":"27","author":"Feng","year":"2016","journal-title":"Chin. Chem. Lett."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1688","DOI":"10.1039\/c3nj41127c","article-title":"From a bodipy-rhodamine scaffold to a ratiometric fluorescent probe for nitric oxide","volume":"37","author":"Yu","year":"2013","journal-title":"New J. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"346","DOI":"10.1038\/345346a0","article-title":"Nitric oxide as an inhibitory non-adrenergic non-cholinergic neurotransmitter","volume":"345","author":"Bult","year":"1990","journal-title":"Nature"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"907","DOI":"10.1038\/ni1001-907","article-title":"Nitric oxide and the immune response","volume":"2","author":"Bogdan","year":"2001","journal-title":"Nat. Immunol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3115","DOI":"10.1021\/ac4041718","article-title":"Highly sensitive low-background fluorescent probes for imaging of nitric oxide in cells and tissues","volume":"86","author":"Zhang","year":"2014","journal-title":"Anal. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1021\/ac403226h","article-title":"Quinoline-based two-photon fluorescent probe for nitric oxide in live cells and tissues","volume":"86","author":"Dong","year":"2014","journal-title":"Anal. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1016\/j.dyepig.2012.08.024","article-title":"A fluorescent and colorimetric chemosensor for nitric oxide based on 1,8-naphthalimide","volume":"96","author":"Wang","year":"2013","journal-title":"Dyes Pigments"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1146\/annurev-biochem-061009-091643","article-title":"Biochemistry of mobile zinc and nitric oxide revealed by fluorescent sensors","volume":"80","author":"Pluth","year":"2011","journal-title":"Annu. Rev. Biochem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"620","DOI":"10.1016\/j.cbpa.2007.09.018","article-title":"Fluorescent probes for nitric oxide and hydrogen peroxide in cell signaling","volume":"11","author":"Miller","year":"2007","journal-title":"Curr. Opin. Chem. Biol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3579","DOI":"10.1039\/c3cc49555h","article-title":"Turn-on fluorescent probes for nitric oxide sensing based on the ortho-hydroxyamino structure showing no interference with dehydroascorbic acid","volume":"50","author":"Beltran","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1920","DOI":"10.1039\/C5SC04415D","article-title":"Engineering a nanolab for the determination of lysosomal nitric oxide by the rational design of a pH-activatable fluorescent probe","volume":"7","author":"Li","year":"2016","journal-title":"Chem. Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1016\/j.talanta.2013.05.043","article-title":"Highly sensitive determination of nitric oxide in biologic samples by a near-infrared bodipy-based fluorescent probe coupled with high-performance liquid chromatography","volume":"116","author":"Zhang","year":"2013","journal-title":"Talanta"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"6475","DOI":"10.1039\/C4CC01142B","article-title":"The rational design of a highly sensitive and selective fluorogenic probe for detecting nitric oxide","volume":"50","author":"Ma","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"12820","DOI":"10.1021\/ja505988g","article-title":"An \u201cenhanced PET\u201d-based fluorescent probe with ultrasensitivity for imaging basal and elesclomol-induced hclo in cancer cells","volume":"136","author":"Zhu","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Zhang, Y.J., and Hu, W. (2017). Energy donor effect on the sensing performance for a series of FRET-based two-photon fluorescent Hg2+ probes. Materials, 10.","DOI":"10.3390\/ma10020108"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1020","DOI":"10.1002\/asia.201501333","article-title":"An approach for the selective detection of nitric oxide in biological systems: An in vitro and in vivo perspective","volume":"11","author":"Gupta","year":"2016","journal-title":"Chem. Asian J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"4783","DOI":"10.1039\/c1cs15037e","article-title":"Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species","volume":"40","author":"Chen","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"9335","DOI":"10.1021\/ac502849d","article-title":"Sensitive naked eye detection of hydrogen sulfide and nitric oxide by aza-bodipy dyes in aqueous medium","volume":"86","author":"Adarsh","year":"2014","journal-title":"Anal. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"17486","DOI":"10.1021\/ja308967u","article-title":"A lysosome-targetable and two-photon fluorescent probe for monitoring endogenous and exogenous nitric oxide in living cells","volume":"134","author":"Yu","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1016\/j.biomaterials.2015.04.012","article-title":"A fast and selective two-photon phosphorescent probe for the imaging of nitric oxide in mitochondria","volume":"58","author":"Chen","year":"2015","journal-title":"Biomaterials"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6548","DOI":"10.1021\/ac501947v","article-title":"Highly sensitive quinoline-based two-photon fluorescent probe for monitoring intracellular free zinc ions","volume":"86","author":"Mao","year":"2014","journal-title":"Anal. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"9915","DOI":"10.1021\/ja404004v","article-title":"A ratiometric two-photon fluorescent probe reveals reduction in mitochondrial H2S production in parkinson\u2019s disease gene knockout astrocytes","volume":"135","author":"Bae","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Zhang, Y.J., and Leng, J.C. (2017). Theoretical studies on two-photon fluorescent Hg2+ probes based on the coumarin-rhodamine system. Sensors, 17.","DOI":"10.3390\/s17071672"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9838","DOI":"10.1021\/ja504015t","article-title":"Molecular engineering of a TBET-based two-photon fluorescent probe for ratiometric imaging of living cells and tissues","volume":"136","author":"Zhou","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1016\/j.dyepig.2011.07.020","article-title":"A naphthalimide-rhodamine ratiometric fluorescent probe for Hg2+ based on fluorescence resonance energy transfer","volume":"92","author":"Liu","year":"2012","journal-title":"Dyes Pigments"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"4185","DOI":"10.1039\/C4CS00280F","article-title":"Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules","volume":"44","author":"Lee","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1039\/C2CS35273G","article-title":"Energy transfer cassettes based on organic fluorophores: Construction and applications in ratiometric sensing","volume":"42","author":"Fan","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1462","DOI":"10.1021\/ol200146j","article-title":"Dicyanostilbene-derived two-photon fluorescence probe for free zinc ions in live cells and tissues with a large two-photon action cross section","volume":"13","author":"Huang","year":"2011","journal-title":"Org. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3483","DOI":"10.1039\/c0cs00224k","article-title":"New sensing mechanisms for design of fluorescent chemosensors emerging in recent years","volume":"40","author":"Wu","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"3684","DOI":"10.1021\/ja042967z","article-title":"Highly sensitive near-infrared fluorescent probes for nitric oxide and their application to isolated organs","volume":"127","author":"Sasaki","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5230","DOI":"10.1039\/C6SC01313A","article-title":"Nir in, far-red out: Developing a two-photon fluorescent probe for tracking nitric oxide in deep tissue","volume":"7","author":"Mao","year":"2016","journal-title":"Chem. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4533","DOI":"10.1039\/C7SC00416H","article-title":"An n-nitrosation reactivity-based two-photon fluorescent probe for the specific in situ detection of nitric oxide","volume":"8","author":"Mao","year":"2017","journal-title":"Chem. Sci."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3869","DOI":"10.1039\/B307732B","article-title":"Influence of electron-acceptor strength on the resonant two-photon absorption cross sections of diphenylaminofluorene-based chromophores","volume":"5","author":"Guo","year":"2003","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"4718","DOI":"10.1021\/jp993803l","article-title":"Solvent-induced two-photon absorption of a push-pull molecule","volume":"104","author":"Luo","year":"2000","journal-title":"J. Phys. Chem. A"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1063\/1.1673778","article-title":"Polarization Dependence of the two-Photon absorption of tumbling molecules with application to liquid 1-chloronaphthalene and benzene","volume":"53","author":"Monson","year":"1970","journal-title":"J. Chem. Phys."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1208","DOI":"10.1063\/1.1579680","article-title":"Solvent effects on the electronic structure of a newly synthesized two-photon polymerization initiator","volume":"119","author":"Wang","year":"2003","journal-title":"J. Chem. Phys."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1653","DOI":"10.1126\/science.281.5383.1653","article-title":"Design of organic molecules with large two-photon absorption cross sections","volume":"281","author":"Albota","year":"1998","journal-title":"Science"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"6378","DOI":"10.1021\/jp810292n","article-title":"Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions","volume":"113","author":"Marenich","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"ref_40","unstructured":"Frisch, G.W.T.M.J., Schlegel, H.B., Scuseria, M.A.R., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, H.N.G.A., Caricato, M., and Li, X. (2009). Gaussian 09, Revision A.1, Gaussian Inc."},{"key":"ref_41","unstructured":"(2013, November 10). Dalton2013. Available online: http:\/\/www.kjemi.uio.no\/software\/dalton\/."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4855","DOI":"10.1021\/jo900588e","article-title":"Tuning the intramolecular charge transfer of alkynylpyrenes: Effect on photophysical properties and its application in design of off\u2212on fluorescent thiol probes","volume":"74","author":"Ji","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"300","DOI":"10.1111\/php.12015","article-title":"A theoretical investigation of two typical two-photon pH fluorescent probes","volume":"89","author":"Xu","year":"2013","journal-title":"Photochem. Photobiol."}],"container-title":["Sensors"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8220\/18\/5\/1324\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:02:03Z","timestamp":1760194923000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8220\/18\/5\/1324"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,4,25]]},"references-count":43,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2018,5]]}},"alternative-id":["s18051324"],"URL":"https:\/\/doi.org\/10.3390\/s18051324","relation":{},"ISSN":["1424-8220"],"issn-type":[{"value":"1424-8220","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,4,25]]}}}