Abstract
In this work, novel β-cyclodextrin-enhanced Eu3+ luminescence aggregates (CELAs) with bright red fluorescence of Eu3+ are prepared. These CELAs exhibit the quick response and highly selective sensitivity at the concentration of 50 µM Fe3+. A series of ligands (such as TTA, phen, β-cyclodextrin) sensitizes the luminescence of Eu3+ (the “antenna effect”), and metal ions–ligands interactions can differentially alter the antenna effect of ligands toward Eu3+. Addition of EDTA to chelate Fe3+ restores the fluorescence, indicating that the fluorescence quenching in the presence of Fe3+ is reversible. This research provides that CELAs integrate these merits of superior lanthanide fluorescence and the amphiphilia property of β-cyclodextrin (β-CD). It is a unique system with enhancement Eu3+ luminescence in ethanol–water system and will be applied for aqueous solution detection sensor with high selectivity and reversibility for Fe3+. On the other hand, the on-off fluorescence property of the CELAs is convenient for environmental detection system.






Similar content being viewed by others
References
Bowyer AA, Shen C, New EJ (2020) A fluorescent three-sensor array for heavy metals in environmental water sources. Analyst 145(4):1195–1201
Vinayak R, Nayek HP (2019) Organotin metalloligands for selective sensing of metal ions. New J Chem 43(19):7259–7268
Senthil Murugan A, Vidhyalakshmi N, Ramesh U, Annaraj J (2017) A Schiff’s base receptor for red fluorescence live cell imaging of Zn2+ ions in zebrafish embryos and naked eye detection of Ni2+ ions for bio-analytical applications. J Mater Chem B 5(17):3195–3200
Saleem M, Lee KH (2015) Optical sensor: a promising strategy for environmental and biomedical monitoring of ionic species. RSC Adv 5(88):72150–72287
You Y, Cho S, Nam W (2014) Cyclometalated iridium(III) complexes for phosphorescence sensing of biological metal ions. Inorg Chem 53(4):1804–1815
Kumari N, Dey N, Jha S, Bhattacharya S (2013) Ratiometric, reversible, and parts per billion level detection of multiple toxic transition metal ions using a single probe in micellar media. ACS Appl Mater Interfaces 5(7):2438–2445
Zhang X, Gou Z, Zuo Y, Lin W (2020) A novel polythioether-based rhodamine B fluorescent probe via successive click reaction and its application in iron ion detection and cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 228:117679
Liu J, Guo Y, Dong B, Sun J, Lyu J, Sun L, Hu S, Xu L, Bai X, Xu W, Mintova S, Song H (2020) Water-soluble coumarin oligomer based ultra-sensitive iron ion probe and applications. Sens Actuators B Chem 320:128361
Lee S, Uliana A, Taylor MK, Chakarawet K, Bandaru SRS, Gul S, Xu J, Ackerman Cheri M, Chatterjee R, Furukawa H, Reimer JA, Yano J, Gadgil A, Long GJ, Grandjean F, Long JR, Chang CJ (2019) Iron detection and remediation with a functionalized porous polymer applied to environmental water samples. Chem Sci 10(27):6651–6660
Mallick D, Biswal B, Thirunavoukkarasu M, Mohanty R, Bag B (2017) Signalling probes appended with two rhodamine derivatives: inter-component preferences, Fe(III)-ion selective fluorescence responses and bio-imaging in plant species. New J Chem 41(24):15144–15156
Mahesh K, Karpagam S (2017) Thiophene-thiazole functionalized oligomers-excellent fluorescent sensing and selective probe for copper and iron ion. Sens Actuators B Chem 251:9–20
Sahoo SK, Sharma D, Bera RK, Crisponi G, Callan JF (2012) Iron(III) selective molecular and supramolecular fluorescent probes. Chem Soc Rev 41(21):7195–7227
Zeng C-H, Meng X-T, Xu S-S, Han L-J, Zhong S, Jia M-Y (2015) A polymorphic lanthanide complex as selective Co2+ sensor and luminescent timer. Sens Actuators B Chem 221:127–135
Hanaoka K, Kikuchi K, Kojima H, Urano Y, Nagano T (2004) Development of a zinc Ion-selective luminescent lanthanide chemosensor for biological applications. J Am Chem Soc 126(39):12470–12476
Zhao Z-P, Jiang Y-F, Chen Y, Li H-R, Zheng Y, Zeng C-H, Zhong S, Guo P, Zhao Y-L (2018) Highly luminescent lanthanide complex as bifunctional sensor for Et2O and Fe2+. J Lumin 204:560–567
Aleem AR, Liu J, Wang J, Wang J, Zhao Y, Wang Y, Wang Y, Wang W, Rehman FUL, Kipper MJ, Tang J (2020) Selective sensing of Cu2+ and Fe3+ Ions with Vis-excitation using fluorescent Eu3+-induced aggregates of polysaccharides (EIAP) in mammalian cells and aqueous systems. J Hazard Mater 399:122991
Wang J, Liu J, Wang J, Wang Y, Cao J, Hou L, Ge R, Chi J, Huang L, Guo J, Aleem AR, Song Z, Tamang SK, Liu J, Wang G, Kipper MJ, Belfiore LA, Tang J (2020) Smart sensing of Cu2+ in living cells by water-soluble and nontoxic Tb3+/Eu3+-induced aggregates of polysaccharides through fluorescence imaging. J Mater Chem C 8(24):8171–8182
Zhao C, Zhao L, Liu X, Meng L (2019) Synthesis and characterization of two Cd (II) complexes constructed with tricarboxylic acids and as a fluorescent probe of iron ions. Inorg Chim Acta 486:48–54
Su H, Wang J, Yan L (2019) Homogeneously Synchronous Degradation of chitin into carbon dots and organic acids in aqueous solution. ACS Sustain Chem Eng 7(22):18476–18482
Sui B, Tang S, Liu T, Kim B, Belfield KD (2014) Novel BODIPY-based fluorescence turn-on sensor for Fe3+ and its bioimaging application in living cells. ACS Appl Mater Interfaces 6(21):18408–18412
Łukasik N, Wagner-Wysiecka E, Małachowska A (2019) Iron(iii)-selective materials based on a catechol-bearing amide for optical sensing. Analyst 144(9):3119–3127
Kagit R, Yildirim M, Ozay O, Yesilot S, Ozay H (2014) Phosphazene based multicentered naked-eye fluorescent sensor with high selectivity for Fe3+ Ions. Inorg Chem 53(4):2144–2151
Weng G, Thanneeru S, He J (2018) Dynamic coordination of Eu–iminodiacetate to control fluorochromic response of polymer hydrogels to multistimuli. Adv Mater 1706526
Binnemans K (2009) Lanthanide-based luminescent hybrid materials. Chem Rev 109(9):4283–4374
Chen P, Li Q, Grindy S, Holtenandersen N (2015) White-light-emitting lanthanide metallogels with tunable luminescence and reversible stimuli-responsive properties. J Am Chem Soc 137(36):11590–11593
Seidi F, Shamsabadi AA, Amini M, Shabanian M, Crespy D (2019) Functional materials generated by allying cyclodextrin-based supramolecular chemistry with living polymerization. Polym Chem 10(27):3674–3711
Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–1754
Serio N, Chanthalyma C, Prignano L, Levine M (2013) Cyclodextrin-enhanced extraction and energy transfer of carcinogens in complex oil environments. ACS Appl Mater Interfaces 5(22):11951–11957
Ren Z, Xu Y, Lu Z, Wang Z, Chen C, Guo Y, Shi X, Li F, Yang J, Zheng Y (2019) Construction of a water-soluble and photostable rubropunctatin/β-cyclodextrin drug carrier. RSC Advances 9(20):11396–11405
Morrison PWJ, Connon CJ, Khutoryanskiy VV (2013) Cyclodextrin-mediated enhancement of riboflavin solubility and corneal permeability. Mol Pharm 10(2):756–762
Samperio C, Boyer R, Eigel WN, Holland KW, McKinney JS, O’Keefe SF, Smith R, Marcy JE (2010) Enhancement of plant essential oils’ aqueous solubility and stability using alpha and beta cyclodextrin. J Agric Food Chem 58(24):12950–12956
Schmidt BVKJ, Hetzer M, Ritter H, Barner-Kowollik C (2014) Complex macromolecular architecture design via cyclodextrin host/guest complexes. Prog Polym Sci 39(1):235–249
Jing J, Szarpak-Jankowska A, Guillot R, Pignot-Paintrand I, Picart C, Auzély-Velty R (2013) Cyclodextrin/paclitaxel complex in biodegradable capsules for breast cancer treatment. Chem Mater 25(19):3867–3873
Sinha A, Jana NR (2015) Separation of microcystin-LR by cyclodextrin-functionalized magnetic composite of colloidal graphene and porous silica. ACS Appl Mater Interfaces 7(18):9911–9919
Sherje AP, Dravyakar BR, Kadam D, Jadhav M (2017) Cyclodextrin-based nanosponges: a critical review. Carbohyd Polym 173:37–49
Schofield WCE, Badyal JPS (2011) Controlled fragrant molecule release from surface-tethered Cyclodextrin host-guest inclusion complexes. ACS Appl Mater Interfaces 3(6):2051–2056
Massaro M, Colletti CG, Lazzara G, Guernelli S, Noto R, Riela S (2017) Synthesis and characterization of halloysite-cyclodextrin Nanosponges for enhanced dyes adsorption. ACS Sustain Chem Eng 5(4):3346–3352
Chen M, Pérez RL, Du P, Bhattarai N, McDonough KC, Ravula S, Kumar R, Mathis JM, Warner IM (2019) Tumor-targeting NIRF NanoGUMBOS with Cyclodextrin-enhanced chemo/photothermal antitumor activities. ACS Appl Mater Interfaces 11(31):27548–27557
Pramanik, A.; Amer, S.; Grynszpan, F.; Levine, M. (2020) Highly sensitive detection of cobalt through fluorescence changes in β-cyclodextrin-bimane complexes. Chemical Communication.
Hayashi N, Chen R, Hiraoka M, Ujihara T, Ikezaki H (2010) β-Cyclodextrin/surface plasmon resonance detection system for sensing bitter-astringent taste intensity of green tea catechins. J Agric Food Chem 58(14):8351–8356
Belica-Pacha S, Miłowska K, Ionov M, Bryszewska M, Buczkowski A, Budryn G, Oracz J, Zaczyńska D, Wróblewska A, Urbaniak P, Pałecz B (2020) The impact of β-cyclodextrin on biological and chemical properties of mianserin hydrochloride in aqueous solution. J Mol Liq 314:113589
Niu H, Chen W, Chen W, Yun Y, Zhong Q, Fu X, Chen H, Liu G (2019) Preparation and characterization of a modified-β-Cyclodextrin/β-Carotene inclusion complex and Its application in pickering emulsions. J Agric Food Chem 67(46):12875–12884
Milović NM, Badjić JD, Kostić NM (2004) Conjugate of palladium(II) complex and β-Cyclodextrin acts as a biomimetic peptidase. J Am Chem Soc 126(3):696–697
Li X, Gao X, Shi W, Ma H (2014) Design strategies for water-soluble small molecular chromogenic and fluorogenic probes. Chem Rev 114(1):590–659
Han C, Wang R, Wang K, Xu H, Sui M, Li J, Xu K (2016) Highly fluorescent carbon dots as selective and sensitive “on-off-on” probes for iron(III) ion and apoferritin detection and imaging in living cells. Biosens Bioelectron 83:229–236
Gunnlaugsson T, Leonard JP, Sénéchal K, Harte AJ (2004) Eu(III)–cyclen–phen conjugate as a luminescent copper sensor: the formation of mixed polymetallic macrocyclic complexes in water. Chem Commun 7:782–783
Guo J, Tang J, Wang J, Mao S, Li H, Wang Y, Liu J, Wang Y, Huang L, Kipper M, Belfiore L (2018) Europium(III)-induced water-soluble nano-aggregates of hyaluronic acid and chitosan: structure and fluorescence. MRS Commun 8:1–6
Li X, Wang J, Liu J, Tang J, Wang J, Guo J, Wang Y, Huang L, Aleem AR, Kipper MJ, Belfiore LA (2019) Strong luminescence and sharp heavy metal ion sensitivity of water-soluble hybrid polysaccharide nanoparticles with Eu3+ and Tb3+ inclusions. Appl Nanosci 9(8):1833–1844
Xue S-F, Chen Z-H, Han X-Y, Lin Z-Y, Wang Q-X, Zhang M, Shi G (2018) DNA encountering terbium(III): a smart, “chemical nose/tongue” for large-scale time-gated luminescent and lifetime-based sensing. Anal Chem 90(5):3443–3451
Acknowledgement
This work is financially supported by Shandong Province Natural Science Foundation (No. ZR2019BD061, SZJ71901CZ, ZR2019PD004), Academy local cooperation fund of Shandong Academy of Sciences (2018CXY-31, 2018CXY-32, 2019-CXY1), foundation of Shandong Academy of Sciences (2019QN0036).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Handling Editor: Joshua Tong.
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Wang, J., Wang, T., Hu, Y. et al. Fe3+ sensitivity fluorescence sensor from β-cyclodextrin-enhanced Eu3+ luminescence aggregates. J Mater Sci 56, 10979–10989 (2021). https://doi.org/10.1007/s10853-021-05961-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-021-05961-8


