Abstract
Solvatochromism is a property of many different compounds in which color change is a consequence of solvent polarity. Strong blue fluorescent aminofuran was synthesized from the three-component reaction. It was found that the product is highly fluorescent and shows solvatochromic shift between 280 and 380 nm in solvents ranging from water to hexane. Solvent effects on the location of the absorption and fluorescence bands were investigated. In this compound, the presence of electron donor–acceptor groups, here amine or carbonyl groups, in its push–pull scaffold affects the potential chemical reactivity within the chemical environments undergoing color change in the presence of metal cations such as copper, mercury, ruthenium, iron and gold as colorimetric sensor. Displaying color change is probably due to the coordination of the amine group to the metal ions. Also, it is sensitive probe for detection of a number of oxidants.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Amendola V, Fabbrizzi L, Mangano C, Pallavicini P (2001) Molecular machines based on metal ion translocation. Acc Chem Res 34:488–493. https://doi.org/10.1021/ar010011c
Ameri M et al (2019) Role of stabilizing surfactants on capacitance, charge, and ion transport in organic nanoparticle-based electronic devices. Appl Mater Interf 11(10):10074–10088. https://doi.org/10.1021/acsami.8b19820
Asghari S, Qandalee M (2007) A facile one-pot synthesis of amino furans using trans-cinnamaldehyde in the presence of nucleophilic isocyanides. Acta Chim Slov 54:638–641
Basurto S, Miguel D, Moreno D, Neo AG, Quesada R, Torroba T (2010) Simple 1-dicyanomethylene-2-chloro-3-aminoindene push–pull chromophores: applications in cation and anion sensing. Org Biomol Chem 8:552–558. https://doi.org/10.1039/B916700E
Bernard V, Isabelle L (2000) Design principles of fluorescent molecular sensors for cation recognition. Coord Chem Rev 205:3–40. https://doi.org/10.1016/S0010-8545(00)00246-0
Caltagirone C, Gale PA (2009) Anion receptor chemistry: highlights from 2007. Chem Soc Rev 38:520. https://doi.org/10.1039/B806422A
Colin CLR, Palmer TF, Robert BC (1984) Chemiluminescence from reactions of bis(pentachloro-phenyl)oxalate, hydrogen peroxide and fluorescent compounds. Role of the fluor and nature of chemielectronic process(es). J Chem Soc Faraday Trans 2(80):837–849. https://doi.org/10.1039/F29848000837
Collot M, Bou S, Fam TK, Richert L, Mély Y, Danglot L, Klymchenko AS (2018) Probing polarity and heterogeneity of lipid droplets in live cells using a push-pull fluorophore. Anal Chem 91:1928–1935. https://doi.org/10.1021/acs.analchem.8b04218
Czarnik AW (1994) Chemical communication in water using fluorescent chemosensors. Acc Chem Res 27:302–308. https://doi.org/10.1021/ar00046a003
de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566. https://doi.org/10.1021/cr960386p
de Silva AP, Mc Caughan BOF, Querol M (2003) Newer optical-based molecular devices from older coordination chemistry. Dalton Trans. https://doi.org/10.1039/B212447P
Fabbrizzi L, Licchelli M, Pallavicini P (1999) Transition metals as switches. Acc Chem Res 32:846–853. https://doi.org/10.1021/ar990013l
Forzani ES, Zhang HQ, Chen W, Tao NQ (2005) Detection of heavy metal ions in drinking water using a high-resolution differential surface plasmon resonance sensor. Environ Sci Technol 39:1257. https://doi.org/10.1021/es049234z
Gale PA, Garcıa-Garrido SE, Garric J (2008) Anion receptors based on organic frameworks: highlights from 2005 and 2006. Chem Soc Rev 37:151. https://doi.org/10.1039/B715825D
Gale PA, Quesada R (2006) Anion coordination and anion-templated assembly: highlights from 2002 to 2004. Coord Chem Rev 250:3219–3244. https://doi.org/10.1016/j.ccr.2006.05.020
Ghaedi M, Ahamadi F, Shokrollahi A (2006) Simultaneous preconcentration and determination of copper, nickel, cobalt and lead ions content by flame atomic absorption spectrometry. J Hazard Mater 142:272–278. https://doi.org/10.1016/j.jhazmat.2006.08.012
Gunnlaugsson T, Glynn M, Tocci GM, Kruger PE, Pfeffer FM (2006) Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors. Coord Chem Rev 250:3094–3117. https://doi.org/10.1016/j.ccr.2006.08.017
Harikrishnan M, Sadhasivam V, Mariyappan M, Murugesan S, Malini N, Siva A (2019) A simple triazine (D-A) based organic fluorophore selective dual sensor for copper(II) and dichromate ions and its solvatochromism, solid state sensing, logic gate applications. Dyes Pigm 168:123–133. https://doi.org/10.1016/j.dyepig.2019.04.041
Hou L, Kong X, Wang Y, Chao J, Li C, Dong C, Wang Y, Shuang S (2017) An anthraquinone-based highly selective colorimetric and fluorometric sensor for sequential detection of Cu2+ and S2− with intracellular application. J Mater Chem B 5:8957–8966. https://doi.org/10.1039/C7TB01596H
Kucherak OA, Didier P, Mely Y, Klymchenko AS (2010) Fluorene analogues of PRODAN with superior fluorescence brightness and solvatochromism. J Phys Chem Lett 1:616–620. https://doi.org/10.1021/jz9003685
Lavigne J, Anslyn EV (2001) Sensing a paradigm shift in the field of molecular recognition: from selective to differential receptors. Angew Chem Int Ed Engl 40:3118–3130. https://doi.org/10.1002/1521-3773(20010903)40:17%3C3118::aid-anie3118%3E3.0.co;2-y
Liu W, Wang Y, Yang J, Li X, Wang X, Ma L (2020) The abnormal solvatochromism, high-contrast mechanochromism and internal mechanism of two AIEE-active β-diketones. Dyes Pigm 175:108149–108156. https://doi.org/10.1016/j.dyepig.2019.108149
Mart´ınez-M´a˜nez R, Sancen´on F (2003) Fluorogenic and chromogenic chemosensors and reagents for anions. Chem Rev 103:4419–4476. https://doi.org/10.1021/cr010421e
Martınez-M´anez R, Sancenon F (2005) New advances in fluorogenic anion chemosensors. J Fluoresc 15:267–285. https://doi.org/10.1007/s10895-005-2626-z
Mataga N, Kaifu Y, Koizumi M (1956) Solvent effects upon fluorescence spectra and the dipole moments of excited molecules. Bull Chem Soc Jpn 29:465–470. https://doi.org/10.1246/bcsj.29.465
Meng X, Li S, Ma W, Wang J, Hu Z, Cao D (2018) Highly sensitive and selective chemosensor for Cu2+ and H2PO4− based on coumarin fluorophore. Dyes Pigm 154:194–198. https://doi.org/10.1016/j.dyepig.2018.03.002
Mohammadi A, Yaghoubi S (2017) Development of a highly selective and colorimetric probe for simultaneous detection of Cu2+ and CN− based on an azo chromophore. Sens Actuators B 251:264–271. https://doi.org/10.1016/j.snb.2017.05.068
Murugan AS, Vidhyalakshmi N, Ramesh U, Annaraj J (2018) In vivo bio-imaging studies of highly selective, sensitive rhodamine based fluorescent chemosensor for the detection of Cu2+/Fe3+ ions. Sensor Actuator B Chem 274:22–29. https://doi.org/10.1016/j.snb.2018.07.104
Muwal PK, Nayal A, Jaiswal MK, Pandey PS (2018) A dipyrromethane based receptor as a dual colorimetric sensor for F− and Cu2+ ions. Tetrahedron Lett 59:29–32. https://doi.org/10.1016/j.tetlet.2017.11.042
Niko Y, Kawauchi S, Konishi G (2013) Solvatochromic pyrene analogues of prodan exhibiting extremely high fluorescence quantum yields in apolar and polar solvents. Chem-Eur J 19:9760–9765. https://doi.org/10.1002/chem.201301020
Norris SR, Warner CC, Lampkin BJ, Bouc P, VanVeller B (2019) Synthesis and spectral properties of push-pull dyes based on isobenzofuran scaffolds. Org Lett 21:3817–3821. https://doi.org/10.1021/acs.orglett.9b01260
Orellana G, Moreno-Bondi MC (2005) Frontiers in chemical sensors: novel principles and techniques. Springer, New York
Prabphal J, Vilaivan T, Praneenararat T (2018) Fabrication of a paper-based turn-off fluorescence sensor for Cu2+ ion from a pyridinium porphyrin. Chem Select 3:894–899. https://doi.org/10.1002/slct.201702382
Prados P, Quesada R (2008) Recent advances in macrocyclic and macrocyclic-based anion receptors. Supramol Chem 20:201–216. https://doi.org/10.1080/10610270701790693
Qin JC, Yang ZY (2015) Designof a novel coumarin-based multifunctional fluorescent probe for Zn2+/Cu2+/S2− in aqueous solution. Mater Sci Eng C 57:265–271. https://doi.org/10.1016/j.msec.2015.07.064
Sessler JL, Gale PA, Cho WS (2006) Anion receptor chemistry. Royal Society of Chemistry, Cambridge, UK. https://doi.org/10.1039/9781847552471
Soylak M, Narin I, Dogan M (1997) Trace enrichment and atomic absorption spectrometric determination of lead, copper, cadmium and nickel in drinking water samples by use of an activated carbon column. Anal Lett 30:2801–2810. https://doi.org/10.1080/00032719708001823
Wang X, Hu J, Zhang G, Liu S (2014) Highly selective fluorogenic multianalyte biosensors constructed via enzyme-catalyzed coupling and aggregation-induced emission. J Am Chem Soc 136:9890–9893. https://doi.org/10.1021/ja505278w
Wang L, Li W, Zhi W, Ye D, Wang Y, Ni L, Bao X (2017) A rapid-responsive fluorescent probe based on coumarin for selective sensing of sulfite in aqueous solution and its bioimaging by turn-on fluorescence signal. Dyes Pigm 147:357–363. https://doi.org/10.1016/j.dyepig.2017.07.021
Wang X, Chen H, Zhao Y, Chen X, Wang X, Chen X (2010) Optical oxygen sensors move towards colorimetric determination. TrAC Trends Anal Chem 29:319–338. https://doi.org/10.1016/j.trac.2010.01.004
Yadav SB, Sonvane SS, Sekar N (2020) Novelblue-green emitting NLO phorictriphenylamine-imidazole based donor-π-acceptor compound: solvatochromism, DFT, TD-DFT and non-linear optical studies. Spectrochim Acta Part A Mol Biomol Spectrosc 224:117421–117429. https://doi.org/10.1016/j.saa.2019.117421
Zargoosh K, Ghayeb Y, Aeineh N, Qandalee M, MiranBeigi A (2013) Furandicarboxylate derivatives as excellent fluorescence standards: spectroscopical and electrochemical study. J Lumin 135:31–37. https://doi.org/10.1016/j.jlumin.2012.10.021
Zhou Q, Zhu Y, Sheng PT, Wu ZM, Cai QY (2014) A highly selective and reversible fluorescent Cu2+ and S2− probe under physiological conditions and in live cells. RSC Adv 4:46951–46954. https://doi.org/10.1039/C4RA03916E
Funding
Funding this project was financially supported by the Burgos University, Spain. The authors would like to thank Professor Tomas Torroba Perez and his group for their generous support and encouragement that kindly cooperated and helped us in this work. Also, we would like to thank Dr Zargoosh from Isfahan University of technology for his valuable advice.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The author does not have any conflict of interest in relation to the work described.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Qandalee, M., Mehdizadeh Naderi, P., Durán-Valle, C.J. et al. Solvatochromism study of donor–acceptor blue fluorophore and its application in cation and oxidant sensing. Chem. Pap. 76, 567–573 (2022). https://doi.org/10.1007/s11696-021-01890-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-021-01890-7