Synthesis and Performances of Triphenylamine Based Turn-on Fluorescent Probe for Fe<sup>3+</sup> by An Enhancement Pattern

Zhu-ye SHANG; Li SHU; Yue WANG; Qing-tao MENG; Hong-min JIA; Zhi-qiang ZHANG

doi:10.37188/CJL.20210386

您当前的位置：

首页 >

文章列表页 >

Synthesis and Performances of Triphenylamine Based Turn-on Fluorescent Probe for Fe³⁺ by An Enhancement Pattern

Luminescence Applications and Interdisciplinary Fields | 更新时间：2022-04-07

- Synthesis and Performances of Triphenylamine Based Turn-on Fluorescent Probe for Fe³⁺ by An Enhancement Pattern
  增强出版
- Chinese Journal of Luminescence Vol. 43, Issue 3, Pages: 453-461(2022)
- 作者机构：
  
  辽宁科技大学　化学工程学院，辽宁　鞍山　114051
- 作者简介：
- 基金信息：
  
  Liaoning “BaiQianWan Talents Program”;Scientific Research Fund General Project of Liaoning Province Department of Education(LJKZ0277);Technological Project of Liaoning Provincial Department of Education(2019LNQN03;2019LNJC18)
- DOI：10.37188/CJL.20210386
  CLC： O482.31
- Published：2022-03，
  
  Received：08 December 2021，
  
  Revised：23 December 2021，
扫描看全文
Zhu-ye SHANG, Li SHU, Yue WANG, et al. Synthesis and Performances of Triphenylamine Based Turn-on Fluorescent Probe for Fe³⁺ by An Enhancement Pattern. [J]. Chinese Journal of Luminescence 43(3):453-461(2022)
DOI：

Zhu-ye SHANG, Li SHU, Yue WANG, et al. Synthesis and Performances of Triphenylamine Based Turn-on Fluorescent Probe for Fe³⁺ by An Enhancement Pattern. [J]. Chinese Journal of Luminescence 43(3):453-461(2022) DOI： 10.37188/CJL.20210386.

摘要

在人的许多生理过程中扮演着重要的角色，例如氧气运输、DNA合成、髓磷脂合成、线粒体呼吸、神经递质合成和代谢等。然而，过量的Fe

会诱导细胞产生·OH从而引起细胞损伤，并且还会诱导β-地中海贫血、帕金森病、癫痫和阿尔茨海默病等疾病的发生。因此，对Fe

的检测和监测具有非常重要的意义。本文设计并合成了一种以三苯胺为母体的增强型Fe

荧光探针

，并将其应用于实际水样中Fe

的识别。结果表明，探针

对Fe

的识别具有较高的灵敏度，其检测限低至0.165 μmol·L

-1

。同时，Fe

的加入会导致探针溶液的荧光颜色由蓝绿色变为黄色，能够达到“裸眼”识别的效果。通过高分辨率质谱证明了探针与Fe

为1∶1配位。利用密度泛函理论计算了识别Fe

前后轨道能级和电能的变化并解释了其荧光光谱现象。

Abstract

plays an important role in many physiological processes

such as oxygen transport

DNA synthesis

myelin synthesis

mitochondrial respiration

neurotransmitter synthesis and metabolism. However

excessive Fe

can induce cells to produce a large amount of ·OH and result in cell damage

which can also cause a variety of diseases

such as β-thalassemia

Parkinson‘s disease

epilepsy and Alzheimer‘s disease. Therefore

it is of great significance to detect and monitor Fe

. In this paper

a fluorescence enhanced Fe

probe

based on triphenylamine is designed and synthesized

and it is also applied to the recognition of Fe

in real water samples. The results show that the probe

has a high sensitivity for Fe

recognition

and the detection limit is as low as 0.165 μmol·L

-1

. At the same time

upon the addition of Fe

an obvious change in the colour of the

solution from turquoise to yellow is observed

allowing for colorimetric detection of Fe

by the "naked eye" . The 1∶1 coordination mode between

and Fe

is further proved by high resolution mass spectrometry. Density functional theory(DFT) is used to calculate the changes of energy level and energy of the orbital before and after coordination with Fe

and explain the phenomenon of its fluorescence spectrum.

关键词

三苯胺铁离子荧光增强型探针裸眼识别

Keywords

triphenylamineiron ionsfluorescent enhanced probenaked-eyerecognition

references

PAN C Q, WANG K, JI S M, et al. Schiff base derived Fe3+-selective fluorescence turn-off chemsensors based on triphenylamine and indole: synthesis,properties and application in living cells [J]. RSC Adv., 2017, 7(57):36007-36014.

曾竟, 刘瑞姣, 陈佳敏. 在双波长下识别Fe3+的一种新型可视化荧光探针的合成及性能 [J]. 发光学报, 2019, 40(4):542-551.

ZENG J, LIU R J, CHEN J M. Synthesis and properties of a novel colorimetric fluorescent probe for Fe3+ at dual emission wavelengths [J]. Chin. J. Lumin., 2019, 40(4):542-551. (in Chinese)

HE B, PUN A B, ZHEREBETSKYY D, et al. New form of an old natural dye:bay-annulated indigo(BAI) as an excellent electron accepting unit for high performance organic semiconductors [J]. J. Am. Chem. Soc., 2014, 136(42):15093-15101.

SUMNER J P, KOPELMAN R. Alexa fluor 488 as an iron sensing molecule and its application in PEBBLE nanosensors [J]. Analyst, 2005, 130(4):528-533.

张文宇, 常青, 周雨锋, 等. 一步合成硫、氮共掺杂的碳量子点及其在Fe3+检测中的应用 [J]. 发光学报, 2016, 37(4):410-415.

ZHANG W Y, CHANG Q, ZHOU Y F, et al. One-step synthesis of sulfur-and nitrogen-co-doped carbon quantum dots for Fe(Ⅲ) detection [J]. Chin. J. Lumin., 2016, 37(4):410-415. (in Chinese)

ZHAO Y Q, DUAN J H, YU L, et al. Metabolic iron detection through divalent metal transporter 1 and ferroportin mediated cocktail fluorogenic probes [J]. Chem. Commun., 2021, 57(64):7902-7905.

TUMAY S O, IRANI-NEZHAD M H, KHATAEE A. Multi-anthracene containing fluorescent probe for spectrofluorimetric iron determination in environmental water samples [J]. Spectrochim. Acta A, 2021, 248:119250-1-9.

LONG L L, WANG N, HAN Y Y. A coumarin-based fluorescent probe for monitoring labile ferrous iron in living system [J]. Analyst, 2018, 143(11):2555-2562.

WARD R J, ZUCCA F A, DUYN J H, et al. The role of iron in brain ageing and neurodegenerative disorders [J]. Lancet Neurol., 2014, 13(10):1045-1060.

WANG W, WU M, LIU H M, et al. A novel on-off-on fluorescent chemosensor for relay detection of Fe3+ and PPi in aqueous solution and living cells [J]. Tetrahedron Lett., 2019, 60(25):1631-1635.

HUANG L, HOU F P, CHENG J, et al. Selective off-on fluorescent chemosensor for detection of Fe3+ ions in aqueous media [J]. Org. Biomol. Chem., 2012, 10(48):9634-9638.

GAO Y, MA S W, YA X Y, et al. A novel isatin-based fluorescent chemosensor:synthesis and recognition behaviour towards Fe (Ⅲ) and PPi in aqueous solution and living cells [J]. Tetrahedron Lett., 2019, 61(5):151452-1-5.

LI Z X, ZHANG L F, LI X Y, et al. A fluorescent color/intensity changed chemosensor for Fe3+ by photo-induced electron transfer(PET) inhibition of fluoranthene derivative [J]. Dyes Pigm., 2012, 94(1):60-65.

刘静, 李东伟, 武小强, 等. 萘酰亚胺铁离子荧光探针的合成及识别性能 [J]. 发光学报, 2017, 38(2):226-231.

LIU J, LI D W, WU X Q, et al. Synthesis and recognition performance of naphthalene imide-iron ion fluorescent probe [J]. Chin. J. Lumin., 2017, 38(2):226-231. (in Chinese)

GHAEDI M, SHOKROLLAHI A, MEHRNOOSH R, et al. Combination of cloud point extraction and flame atomic absorption spectrometry for preconcentration and determination of trace iron in environmental and biological samples [J]. Cent. Eur. J. Chem., 2008, 6(3):488-496.

BAE S, TAE J. Rhodamine-hydroxamate-based fluorescent chemosensor for FeⅢ [J]. Tetrahedron Lett., 2007, 48(31):5389-5392.

EBRAHIMI-NAJAFABADI H, PASDARAN A, BEZENJANI R R, et al. Determination of toxic heavy metals in rice samples using ultrasound assisted emulsification microextraction combined with inductively coupled plasma optical emission spectroscopy [J]. Food Chem., 2019, 289:26-32.

LIN Y T, HOANG H, HSIEHS I, et al. Manganous ion supplementation accelerates wild type development,enhances stress resistance,and rescues the life span of a short-lived Caenorhabditis elegans mutant [J]. Free Radical Biol. Med., 2006, 40(7):1185-1193.

REKHI H, RANI S, SHARMA N, et al. A review on recent applications of high-performance liquid chromatography in metal determination and speciation analysis [J]. Crit. Rev. Anal. Chem., 2017, 47:524-537.

SEIDI S, ALAVI L. Novel and rapid deep eutectic solvent(DES) homogeneous liquid-liquid microextraction(HLLME) with flame atomic absorption spectrometry(FAAS) detection for the determination of copper in vegetables [J]. Anal. Lett., 2019, 52(13):2092-2106.

HIRAYAMA T, TSUBOI H, NIWA M, et al. A universal fluorogenic switch for Fe(Ⅱ) ion based on N-oxide chemistry permits the visualization of intracellular redox equilibrium shift towards labile iron in hypoxic tumor cells [J]. Chem. Sci., 2017, 8(7):4858-4866.

MALIK L A, BASHIR A, QUREASHI A, et al. Detection and removal of heavy metal ions:a review [J]. Environ. Chem. Lett., 2019, 17(4):1495-1521.

LU Y Y, LIANG X Q, NIYUNGEKO C, et al. A review of the identification and detection of heavy metal ions in the environment by voltammetry [J]. Talanta, 2018, 178:324-338.

BANSOD B K, KUMAR T, THAKUR R, et al. A review on various electrochemical techniques for heavy metal ions detection with different sensing platforms [J]. Biosens. Bioelectron., 2017, 94:443-455.

ZHANG X M, GOU Z M, ZUO Y J, et al. A novel polythioether-based rhodamine B fluorescent probe via successive click reaction and its application in iron ion detection and cell imaging [J]. Spectrochim. Acta A, 2020, 228:117679-1-7.

GAO H F, QI H T, PENG Y J, et al. Rapid “turn-on”photoluminescence detection of bisulfite in wines and living cells with a formyl bearing bis-cyclometalated Ir(Ⅲ) complex [J]. Analyst, 2018, 143(15):3670-3676.

LI K, LI LL, ZHOU Q, et al. Reaction-based fluorescent probes for SO2 derivatives and their biological applications [J]. Coord. Chem. Rev., 2019, 388:310-333.

ZHOU F, FENG H, LI H B, et al. Red-emission probe for ratiometric fluorescent detection of bisulfite and its application in live animals and food samples [J]. ACS Omega, 2020, 5(10):5452-5459.

林静, 邵康, 王锴, 等. 近红外长余辉纳米探针ZnGa2O4∶Cr3+,Sn4+的制备及Fe3+含量的时间分辨检测 [J]. 发光学报, 2020, 41(6):734-743.

LIN J, SHAO K, WANG K, et al. Synthesis of near-infrared persistent luminescent nanoprobe ZnGa2O4∶Cr3+,Sn4+ and detection of Fe3+ with time-resolved spectra technique [J]. Chin. J. Lumin., 2020, 41(6):734-743. (in Chinese)

WANG F Y, YU S J, XU Z A, et al. Acid-promoted D-A-D type far-red fluorescent probe with high photostability for lysosomal nitric oxide imaging [J]. Anal. Chem., 2018, 90(13):7953-7962.

DUAN J D, PAN H H, WEI C T, et al. Synthesis and physical properties of triphenylamine-functionalized twistacenes:blue-emitting fluorophores [J]. RSC Adv., 2017, 7(17):10570-10574.

HE K Q, SU N, YU J T, et al. Dinuclear cyclometalated iridium(Ⅲ) complex containing functionalized triphenylamine core:synthesis,photophysics and application in the single-emissive-layer WOLEDs [J]. Tetrahedron, 2016, 72(45):7164-7169.

KEAWIN T, PRACHUMRAK N, NAMUANGRUK S, et al. Efficient bifunctional materials based on pyrene- and triphenylamine-functionalized dendrimers for electroluminescent devices [J]. RSC Adv., 2015, 5(90):73481-73489.

Views

135

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Synthesis and Spectral Properties of Zinc Ion-enhanced Fluorescence Probe Based on Naphthoyl Acylhydrazone

Synthesis of Ratiometric Fluorescent Probe for The Recognition of Glutathione

Synthesis and Immobilization of Water-solubility Fluorescent Probe and Recognition of Mercury(Ⅱ) Ions in Water

Electroluminescent Performances of Red Phosphorescent Iridium Complexes with Carrier Groups

Related Author

Zhi-qiang ZHANG

Zhu-ye SHANG

Li SHU

Yue WANG

Qing-tao MENG

Hong-min JIA

WU Hong-mei

GUO Yu

Related Institution

School of Chemical Engineering， University of Science and Technology Liaoning

School of Chemical and Environmental Engineering, Liaoning University of Technology

College of Mechanical Engineering and Automation, Liaoning University of Technology

Chemistry College, Dalian University of Technology

State Key Laboratory of Fine Chemicals, Dalian University of Technology

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰

Synthesis and Performances of Triphenylamine Based Turn-on Fluorescent Probe for Fe3+ by An Enhancement Pattern

DOI：10.37188/CJL.20210386

摘要

Abstract

关键词

Keywords

references

Synthesis and Performances of Triphenylamine Based Turn-on Fluorescent Probe for Fe³⁺ by An Enhancement Pattern