Synthesis of a Novel Water-Soluble Rhodamine-Based Fluorescent Probe and Its Selective Detection of Free Trivalent Ions

doi:10.19894/j.issn.1000-0518.210041

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (02): 241-246.DOI: 10.19894/j.issn.1000-0518.210041

• Full Papers • Previous Articles Next Articles

Synthesis of a Novel Water-Soluble Rhodamine-Based Fluorescent Probe and Its Selective Detection of Free Trivalent Ions

Shu-Hua HOU, Shi-Qi LI, Li-Jun TANG()

College of Chemistry and Materials Engineering, Bohai University, Jinzhou 121013, China

Received:2021-01-23 Accepted:2021-07-07 Published:2022-02-10 Online:2022-02-09
Contact: Li-Jun TANG
Supported by:
National Natural Science Foundation of China(21878023);Liaoning Revitalization Talents Program and Liaoning Provincial Education Department(LQJ2019005)

1. .pdf(412KB)

Abstract

Abstract:

A novel water-soluble probe (L) is designed and synthesized based on rhodamine B. The results indicate that probe L is a "turn-on" fluorescent probe with high selectivity for free M³⁺ (Cr³⁺, Al³⁺, Fe³⁺) detection in pure water system (TRIS, pH=7.4). The detection limits of probe L to Cr³⁺, Al³⁺, and Fe³⁺ are 1.57×10^-5, 1.43×10^-5, and 6.55×10^-5mol/L, respectively. The probe L has potential applications in detection of trivalent metal ions in biological systems and environments.

Key words: Probe, Ion recognition, Fe³⁺, Al³⁺, Cr³⁺

CLC Number:

O657

Shu-Hua HOU, Shi-Qi LI, Li-Jun TANG. Synthesis of a Novel Water-Soluble Rhodamine-Based Fluorescent Probe and Its Selective Detection of Free Trivalent Ions[J]. Chinese Journal of Applied Chemistry, 2022, 39(02): 241-246.

Figures/Tables 6

Scheme 1　Synthesis of probe L

Fig.1 （A）The UV absorption spectra of various metal ions（10 mmol／L）added to probe L（1.0×10－5mol／L）.（B）Fluorescence spectra of various metal ions（10 mmol／L）added to probe L（1.0×10－5mol／L）：（a）probe L add Fe3+；（b）probe L add Al3+；（c）probe L add Cr3+

Fig.2 The fluorescence emission spectra of the probe L（1.0×10－5mol／L）in TRIS（λex＝510 nm）in the coexistence of other metal ions and Cr3+

Fig.3 Fluorescence emission spectra of probe L in the presence of Cr3+with different concentrations（λex＝510 nm）

Fig.4 Job′s plot of probe L with Cr3+

Scheme 2　Cooperation mecanism of probe L

References 27

[1]	CHEN X J, SHEN X Y, GUAN E, et al. A pyridinyl-functionalized tetraphenylethylene fluorogen for specific sensing of trivalent cations[J]. Chem Commun, 2013:1503-1505.
[2]	GOSWAMI S, AICH K, DAS S, et al. A red fluorescence“off-on”molecular switch for selective detection of Al³⁺, Fe³⁺and Cr³⁺: experimental and theoretical studies along with living cell imaging[J]. Chem Commun, 2013, 49(91):10739-10741.
[3]	WANG J, LI Y, PATEL N G, et al. A single molecular probe for multi-analyte (Cr³⁺, Al³⁺and Fe³⁺) detection in aqueous medium and its biological application[J]. Chem Commun, 2014, 50(82):12258-12261.
[4]	ZHU J L, ZHANG Y H, WANG L, et al. A simple turn-on Schiff base fluorescence sensor for aluminum ion[J]. Tetrahedron Lett, 2016:3535-3539.
[5]	YANG L, DAN W, ZHENG X J, et al. Binding site-driven sensing properties of a quinazoline derivative with metal cations[J]. RSC Adv, 2015, 5(46):36987.
[6]	PAUL S, MANNA A, GOSWAMI S. A differentially selective molecular probe for detection of trivalent ions (Al³⁺, Cr³⁺and Fe³⁺) upon single excitation in mixed aqueous medium[J]. Dalton Trans, 2015, 44(26):11805-11810.
[7]	CHEREDDY N R, SARANRAJ K, BARUI A K, et al. Donor atom selective coordination of Fe³⁺and Cr³⁺trigger fluorophore specific emission in a rhodamine-naphthalimide dyad[J]. RSC Adv, 2014, 4(46):24324-24327.
[8]	GOSWAMI S, AICH K, DAS A K, et al. A naphthalimide-quinoline based probe for selective, fluorescence ratiometric sensing of trivalent ions[J]. RSC Adv, 2013, 3(7):2412-2416.
[9]	ANA M C, SALVADOR G, MARGARITA P, et al. 5, 5′-Bis-vanillin derivatives as discriminating sensors for trivalent cations[J]. Tetrahedron Lett, 2015, 56(26):3988-3991.
[10]	SAMANTA S, RAY T, HAQUE F, et al. A turn-on Rhodamine B-indole based fluorogenic probe for selective sensing of trivalent ions[J]. J Lumin, 2016, 171:13-18.
[11]	ZHU J L, ZHANG Y H, CHEN Y H, et al. A Schiff base fluorescence probe for highly selective turn-on recognition of Zn²⁺ [J]. Tetrahedron Lett, 2017, 58(4):365-370.
[12]	KIM Y S, PARK G J, LEE J J, et al. Multiple target chemosensor: a fluorescent sensor for Zn (Ⅱ) and Al (Ⅲ) and a chromogenic sensor for Fe (Ⅱ) and Fe (Ⅲ)[J]. RSC Adv, 2015, 5:11229-11239.
[13]	ZHAO X, YIN G, JIN D, et al. A sensitive colorimetric and ratiometric chemosensor for trivalent metal cations[J]. J Fluoresc, 2015, 25(2):327-333.
[14]	侯淑华, 王思琦, 曲忠国, 等. 一种荧光增强型三价金属离子荧光探针的合成及性质[J]. 有机化学, 2017, 37(3):726-730.
	HOU S H, WANG S Q, QU Z G, et al. A fluorescence enhancement probe for trivalent ions: preparation and property[J]. Chinese J Org Chem, 2017, 37(3):726-730.
[15]	胡伟, 刘玉婕, 田茂忠, 等. 罗丹明类Fe³⁺荧光探针的合成及光谱性能的研究[J]. 化学试剂, 2019, 41(12):1303-1306.
	HU W, LIU Y J, TIAN M Z, et al. Synthesis and spectral properties of rhodamine like Fe³⁺fluorescent probes[J]. Chinese J Chem Reag, 2019, 41(12):1303-1306.
[16]	WANG L, YANG L, CAO D. A visual and fluorometric probe for Al (Ⅲ) and Fe (Ⅲ) using diketopyrrolopyrrole-based Schiff base[J]. Sens Actuators B, 2014, 202:949-958.
[17]	付大勇, 袁文静, 王伟. 一种新型荧光探针的合成及其对Ag⁺识别性能研究[J]. 化学世界, 2020, 61(3):171-175.
	FU D Y, YUAN W J, WANG W. Synthesis of a novel fluorescent probe and its recognition performance for Ag⁺ [J]. J Chem World, 2020, 61(3):171-175.
[18]	田芳. 罗丹明类荧光探针在重金属和过渡金属离子检测中的应用[J]. 石化技术, 2019, 26(12):364-365.
	TIAN F. Application of rhodamine fluorescent probes in the detection of heavy metals and transition metal ions[J]. Petrochem Technol, 2019, 26(12):364-365.
[19]	张斌, 黄婉婷, 王昕晨, 等. 罗丹明B类衍生物荧光探针的研究进展[J]. 吉林医药学院学报, 2019, 40(4):288-290.
	ZHANG B, HUANG W T, WANG X C, et al. Research progress on fluorescent probes of Rhodamine B derivatives[J]. J Jilin Med College, 2019, 40(4):288-290.
[20]	BARBA-BON A, CALABUIG L, COSTERO A M, et al. Off-on BODIPY-based chemosensors for selective detection of Al³⁺and Cr³⁺versus Fe³⁺in aqueous media[J]. RSC Adv, 2014, 4:8962-8965.
[21]	VENKATESWARULU M, MUKHERJEE T, MUKHERJEE S, et al. Turn-on trivalent cation selective chemodosimetric probe to image native cellular iron pools[J]. Dalton Trans, 2014, 43(14):5269-5273.
[22]	侯淑华, 曲忠国, 钟克利, 等. 一种苯并噻唑-罗丹明衍生物的合成及其对Fe³⁺、Al³⁺、Cr³⁺的识别[J]. 有机化学, 2016, 36(4):768-773.
	HOU S H, QU Z G, ZHONG K L, et al. Synthesis of a novel benzothiazole-rhodamine derivative and its selective detection of Fe³⁺, Al³⁺and Cr³⁺ [J]. Chinese J Org Chem, 2016, 36(4):768-773.
[23]	TANG L J, XIA J Y, ZHONG K L, et al. A simple AIE-active fluorogen for relay recognition of Cu²⁺and pyrophosphate through aggregation-switching strategy[J]. Dyes Pigm, 2020, 178:108379.
[24]	TANG L J, ZHOU L, YAN X M, et al. A new NIR-emissive fluorescence turn-on probe for Hg²⁺detection with a large Stokes shift and its multiple applications[J]. J Photochem Photobiol A, 2020, 387:112160.
[25]	TANG L J, HE P, YAN X M, et al. A mitochondria-targetable fluorescent probe for ratiometric detection of SO₂derivatives and its application in live cell imaging[J]. Sens Actuators B, 2017, 247:421-427.
[26]	SINGH A, SINGH R, SHELLAIAH M, et al. A new pyrene-based aggregation induced ratiometric emission probe for selective detections of trivalent metal ions and its living cell application[J]. Sens Actuators B, 2015, 207(Pt. A):338-345.
[27]	曲忠国. 新型罗丹明类荧光探针的合成及其对Fe³⁺、Al³⁺、Cr³⁺识别性能的研究[D]. 锦州:渤海大学, 2016.
	QU Z G. Synthesis of novel rhodamine-based fluorescent probes and their recognition performance for Fe³⁺, Al³⁺and Cr³⁺ [D]. Jinzhou:BoHai University, 2016.

Synthesis of a Novel Water-Soluble Rhodamine-Based Fluorescent Probe and Its Selective Detection of Free Trivalent Ions

RichHTML

PDF

Supplement

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 6

References 27

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hong-Li YU, Si-Yi ZHOU, Chen HONG, Wen LUO. A Flavone-based “Off-On” Fluorescence Probe for Detecting Butyrylcholinesterase in Living Cell [J]. Chinese Journal of Applied Chemistry, 2023, 40(4): 500-508.
[2]	Jia-Mei GENG, Su-Fang MA, Wen LIU, Hai-Peng DIAO, Zhi-Fang WU, Si-Jin LI. Liver-Targeted Fluorescent Probes for Specific Detection of ONOO^- in HepG2 Cells [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 441-448.
[3]	Song-Song XUE, Zheng-Feng XIE, Jia-Wei HE, Tian-Yi ZHANG, Bao-Ping XIA, Yu-Qin LI. Synthesis of Sulfonylhydrazone Probe with High Selectivity and Rapid Identification of Hg（Ⅱ） Ion and Its Application in Adsorption [J]. Chinese Journal of Applied Chemistry, 2022, 39(5): 760-768.
[4]	Rui HUANG, Chang-Qing YE, Ya-Jun LI, Mong-Feng CHIOU, Da-Liang LI, Hong-Li BAO. Progress of Mitochondria⁃Targeted Near⁃Infrared HClO/ClO^- Fluorescent Probes [J]. Chinese Journal of Applied Chemistry, 2022, 39(3): 407-424.
[5]	Cheng-Lu ZHANG, Yi-Ming WANG, Zhi-Xuan REN, Lu LI, Yu-Qing LI, Fu-Lu SONG. Fluorescent Probe for Rapid Detection of H₂S with Benzimidazole Naphthalimide as the Core [J]. Chinese Journal of Applied Chemistry, 2022, 39(3): 489-497.
[6]	Si-Wei YU, Liang-Peng WANG, Ri-Zhe JIN, Chuan-Qing KANG. Recognition of ClO^－ and Cellular Imaging with Xanthene-based Fluorescent Probes [J]. Chinese Journal of Applied Chemistry, 2022, 39(12): 1903-1911.
[7]	Mei-Ling YAN, Hong-Zhen PENG, Ting-Ting ZUO, Tian TIAN, Ying ZHU, Yan-Hong SUN. Controllable Assembly and Properties of Brain Targeting Peptides with Tetrahedral Framework Nucleic Acids [J]. Chinese Journal of Applied Chemistry, 2022, 39(10): 1501-1509.
[8]	ZHANG Cheng-Lu, BAO Jin-Di, YU Feng-Ming, DONG Wen-Jing, ZHANG Yang, GONG Rong-Qing, ZHANG Yan-Peng, ZHANG Lu. Synthesis and Application of a Fluorescence Probe with Quinazolinone as the Core Block for Highly Selective and Sensitive Detection of Hypochlorite Ion [J]. Chinese Journal of Applied Chemistry, 2021, 38(8): 986-994.
[9]	WEN Guang-Ming, JIAO Ting, DU Xiao-Yan, LI Zhong-Ping. Preparation and Application of Sulfur and Nitrogen Co-doped Carbon Quantum Dots [J]. Chinese Journal of Applied Chemistry, 2021, 38(6): 722-730.
[10]	HUANG Yi-Wen, WANG Li-Yan, ZHAO Bing, SONG Bo. Synthesis of Water Soluble Methoxynaphthene Hemicine for Detection of Chromium(Ⅲ) Ion [J]. Chinese Journal of Applied Chemistry, 2021, 38(11): 1503-1511.
[11]	HU Guowen, QIAO Yuling. Folic Acid-Carbon Dot Conjugates for Cancer Cell Targeting [J]. Chinese Journal of Applied Chemistry, 2020, 37(9): 1003-1009.
[12]	HU Guowen, QIAO Yuling. Folic Acid-Carbon Dot Conjugates for Cancer Cell Targeting [J]. Chinese Journal of Applied Chemistry, 2020, 37(9): 0-0.
[13]	XU Liping, LIU Qingshi, DONG Zhichen, GUO Xingjia, DONG Wei. Simple, Fast and Accurate Detection of Ciprofloxacin Based on Fluorescence Enhancement of Nitrogen-Doped Carbon Dots [J]. Chinese Journal of Applied Chemistry, 2020, 37(7): 830-838.
[14]	CAI Fengze, XU Yongling, ZHOU Le, XU Bingsong, CHEN Hao, SUN Jianqiang, LI Di, WANG Hui. Synthesis and Properties of Red-Emitting Fluorescence Probe for Viscosity Detection [J]. Chinese Journal of Applied Chemistry, 2020, 37(4): 440-446.
[15]	DONG Ziyue, ZHOU Xiaoxia, ZHAO Xiaohui, YE Daying, AN Yue. A Heterocyclic Aromatic Halide Small Molecule Fluorescent Probe for the Detection of 2,4,6-Trinitrophenol [J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 332-339.