Synthesis and Properties of Quinoline Substituted Boron Dipyrromethene Based Ferric Ion Probe

doi:10.11944/j.issn.1000-0518.2018.01.170340

Chinese Journal of Applied Chemistry ›› 2018, Vol. 35 ›› Issue (1): 46-52.DOI: 10.11944/j.issn.1000-0518.2018.01.170340

• Full Papers • Previous Articles Next Articles

Synthesis and Properties of Quinoline Substituted Boron Dipyrromethene Based Ferric Ion Probe

WANG Zhaoyun,ZHANG Ping,ZHANG Min,JIAO Lijuan()

College of Chemistry and Materials Science,Anhui Normal University,Wuhu,Anhui 241000,China

Received:2017-09-18 Accepted:2017-11-24 Published:2018-01-03 Online:2018-01-03
Contact: JIAO Lijuan
Supported by:
Supported by the National Natural Science Foundation of China(No.21372011), the Natural Science Foundation of Anhui Province(No.1508085J07)

Abstract

Abstract:

A quinoline substituted boron dipyrromethene(BODIPY) based probe(BHQ) was synthesized and characterized by nuclear magnetic resonance spectroscopy(NMR) and high resolution mass spectrometer(HRMS). The probe shows significant enhancement of fluorescence intensity in the presence of Fe³⁺ in aqueous solution. The probe exhibits fast response, high sensitivity and high selectivity toward Fe³⁺, while other common metal ions do not show significant interference. The binding between the probe and Fe³⁺ has been found to be in 1:1 mole ratio based on Job's plot. This result suggests that the probe BHQ has potential application in the determination of Fe³⁺ ions.

Key words: boron dipyrromethene, quinoline derivatives, fluorescent probe, ion sensing, ferric ion

WANG Zhaoyun, ZHANG Ping, ZHANG Min, JIAO Lijuan. Synthesis and Properties of Quinoline Substituted Boron Dipyrromethene Based Ferric Ion Probe[J]. Chinese Journal of Applied Chemistry, 2018, 35(1): 46-52.

References

[1]	Zhu H,Fan J,Peng X,et al.Fluorescent Probes for Sensing and Imaging Within Specific Cellular Organelles[J]. Acc Chem Res,2016,49(10):2115-2126.
[2]	CHEN Hongrong, WU Ya'nan,CHEN Shiyan, et al. “Naked Eye” and Fluorescence “Turn On” Recognition of Al3+ Based on 2-Hydroxy-Naphthalene-Formaldehyde Benzoyl-Hydrazone Derivatives[J]. Chinese J Appl Chem,2016,33(5):559-605(in Chinese). 陈虹蓉,伍亚男,陈仕焰,等. 2-羟基萘甲醛苯甲酰腙衍生物对Al3+的裸眼识别和荧光传感[J]. 应用化学,2016,33(5):559-605.
[3]	Ow H,Larson D R,Srivastava M. Bright and Stable Core- Shell Fluorescent Silica Nanoparticles[J]. Nano Lett,2005,5(1):113-117.
[4]	Gao H F,Krzysztof K. Synthesis of Star Polymers by a Combination of ATRP and the Click' Coupling Method[J]. Macromolecules,2006,39(15):4960-4965.
[5]	Nathaniel C L,Svetlana V P,Christian B. Squaramide Hydroxamate Based Chemidosimeter Responding to Iron(Ⅲ) with a Fluorescence Intensity Increase[J]. Inorg Chem,2009,48(3):1173-1182.
[6]	Emerit J, Beaumont C T F. Iron Metabolism, Free Radicals, and Oxidative Injury[J]. Biomed Pharmacother,2001,55(6):333-339.
[7]	Papanikolaou G,Pantopoulos K. Ironmetabolism and Toxicity[J]. Toxicol Appl Pharmacol,2005,202(2):199-211.
[8]	Tesfaldet Z O,van Staden J F,Stefan R I. Sequential Injection Spectrophotometric Determination of Iron as Fe(Ⅱ) in Multi-Vitamin Preparations Using 1,10-Phenanthroline as Complexing Agent[J]. Talanta,2004,64(5):1189-1195.
[9]	Elrod V A,Johnson K S,Coale K H. Determination of Subnanomolar Levels of Iron(Ⅱ) and Total Dissolved Iron in Seawater by Flow Injection and Analysis with Chemiluminescence Detection[J]. Anal Chem,1991,63(9):893-898.
[10]	Ohashi A,Ito H,Kanai C,et al.Cloud Point Extraction of Iron(Ⅲ) and Vanadium(Ⅴ) Using 8-Quinolinol Derivatives and Triton X-100 and Determination of 10-7 mol·dm-3 Level Iron(Ⅲ) in Riverine Water Reference by a Graphite Furnace Atomic Absorption Spectroscopy[J]. Talanta,2005,65(2):525-530.
[11]	Suban K S,Darshna S,Rati K B. Iron(Ⅲ) Selective Molecular and Supramolecular Fluorescent Probes[J]. Chem Soc Rev,2012,41(21):7195-7227.
[12]	Narendra R C,Sathiah T,Asit B M. A Highly Selective Efficient Single Molecular FRET Based Sensor for Ratiometric Detection of Fe3+ Ions[J]. Analyst,2013,138(5):1334-1337.
[13]	Zhou X,Zhou J. Improving the Signal Sensitivity and Photostability of DNA Hybridizations on Microarrays by Using Dye-Doped Core-Shell Silica[J]. Anal Chem,2004,76(18):5302-5312.
[14]	Loudet A,Burgess K. BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties[J]. Chem Rev,2007,39(7):4891-4932.
[15]	Bagwe R P,Yang C,Hilliard L R,et al.Optimization of Dye-Doped Silica Nanoparticles Prepared Using a Reverse Microemulsion Method[J]. Langmuir,2004,20(19):8336-8342.
[16]	Montalti M,Prodi L,Zaccheroni N,et al.Luminescent Anion Sensor Based on a Europium Hybrid Complex[J]. J Am Chem Soc,2001,123(50):12694-12695.
[17]	Hao E,Meng T,Zhang M,et al.Solvent Dependent Fluorescent Properties of a 1,2,3-Triazole Linked 8-Hydroxyquinoline Chemosensor: Tunable Detection from Zinc(Ⅱ) to Iron(Ⅲ) in the CH3CN/H2O System[J]. J Phys Chem A,2011,115(29):8234-8241.
[18]	Zhang M,Hao E H,Xu Y J,et al.One-pot Efficient Synthesis of Pyrrolyl BODIPY Dyes from Pyrrole and Acyl Chloride[J]. RSC Adv,2012,2(30):11215-11218.
[19]	ZHANG Ping,MENG Ting,HAO Erhong. Synthesis and Optical Properties of a Novel Quinoline Derivative as a High Seclective Fluorosensor for Fe(Ⅲ)[J]. J Anhui Norm Univ,2015,38(1):8-13(in Chinese). 张萍,孟婷,郝二宏. 高选择性新型喹啉衍生物Fe3+荧光探针的合成及光学性质研究[J]. 安徽师范大学学报,2015,38(1):8-13.
[20]	Groves B R,Crawford S M,Lundrigan T,et al.Synthesis and Characterisation of the Unsubstituled Dipyrrin and 4,4-Dichloro-4-Bora-3a,4a-Diaza-S-Indacene:Improved Synthesis and Functionalisation of the Simplest BODIPY Framework[J]. Chem Commun,2013,49(8):816-818.
[21]	Zachary D H,Patrick M. Novel Approach to Job's Method[J]. J Chem Edu,1986,63(2):162-167.
[22]	Wang Z,Wang H,Meng T,et al.Synthetically Simple, Click-Generated Quinoline-Based Fe3+ Sensors[J]. Methods Appl Fluores,2017,5(2):024015.

Synthesis and Properties of Quinoline Substituted Boron Dipyrromethene Based Ferric Ion Probe

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	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.
[3]	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.
[4]	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.
[5]	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.
[6]	ZHANG Jin-Hong, SHI Kui, XU Peng, LI Qian, XUE Long-Jian. Regulation of Friction Force of a Water Droplet on Bioinspired Surface [J]. Chinese Journal of Applied Chemistry, 2022, 39(1): 188-195.
[7]	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.
[8]	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.
[9]	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.
[10]	GAO Man, HE Xin, CUI Jingnan, LIU Tao, TIAN Zhenhao, HE Shengui. A Coumarin-Based Fluorescent Probe for Rapid Detection of Endogenous Formaldehyde [J]. Chinese Journal of Applied Chemistry, 2019, 36(9): 1053-1060.
[11]	PAN Wenhui,LI Wen,QU Jinghan,YE Yipei,QU Junle,YANG Zhigang. Research Progress on Organic Fluorescent Probes for Single Molecule Localization Microscopy [J]. Chinese Journal of Applied Chemistry, 2019, 36(3): 269-281.
[12]	SU Ce, CHANG Kaishan, LI Siliang, LI Guanbin, ZHANG Hongbo, BAI Lingling. Synthesis and Properties of a Zn²⁺ Fluorescent Probe Based on Coumarins [J]. Chinese Journal of Applied Chemistry, 2018, 35(5): 532-537.
[13]	CHEN Fan, GUO Zhiqian, ZHU Weihong. Synthesis and Characterization of pH and Temperature Sensitive Polymeric Fluorescent Probe [J]. Chinese Journal of Applied Chemistry, 2018, 35(4): 401-409.
[14]	YIN Zhengri. A Renewable High Selective Fluorescent Probe for Hydrogen Sulfide [J]. Chinese Journal of Applied Chemistry, 2018, 35(12): 1514-1520.
[15]	XU Yulin,LIU Chunrong. Research Progress on Fluorescence Detection of Methionine Sulfoxide/Methionine Sulfoxide Reductases [J]. Chinese Journal of Applied Chemistry, 2018, 35(1): 21-27.