Synthesis of Isomers of Distinguishable Iron（Ⅲ） Fluorescent Probes and Application in Water Samples

doi:10.19894/j.issn.1000-0518.210147

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (5): 787-796.DOI: 10.19894/j.issn.1000-0518.210147

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Synthesis of Isomers of Distinguishable Iron（Ⅲ） Fluorescent Probes and Application in Water Samples

Jing-Hui WEN¹, Bing ZHAO¹^,²(), Wei KAN¹^,², Li-Yan WANG¹^,², Li SUN¹, Tian-Shu SONG¹, Bo SONG¹^,²

^1.College of Chemistry and Chemical Engineering，Qiqihar University，Qiqihar 161006，China
^2.Heilongjiang Provincial Key Laboratory of Surface Active Agent and Auxiliary，Qiqihar 161006，China

Received:2021-04-12 Accepted:2021-08-27 Published:2022-05-01 Online:2022-05-24
Contact: Bing ZHAO
About author:zhao_submit@aliyun.com
Supported by:
the National Natural Science Foundation of China(21978140);the Natural Science Foundation of Heilongjiang Province(LC2017004);the Fundamental Research Funds in Heilongjiang Provincial Universities(YSTSXK201853);the Echelon Reserve Leader Fund for the Leading Talent of Heilongjiang Province(HLJLY2018008);Qiqihar University Graduate Innovation Fund Grants(YJSCX2019037)

Abstract

Abstract:

Two isomeric phenanthro［9，10-d］imidazole-phenol derivatives （PI?o?OH and PI?m?OH） were synthesized by the reaction of isomeric 2-aminophenyl and 3-aminophenyl phenanthro［9，10-d］imidazole and 5-nitro salicylaldehyde. In the aqueous medium （V（DMF）∶V（HEPES） = 1∶1， pH = 7.4）， fluorescent intensities for two isomers were observed and the fluorescence was quenched by the addition of Fe³⁺ with the quenching ratio of 1/3 and 1/6. The quenching effects are not disturbed by other metal ions and pH value with the quenching constants K_sv of 4.8×10³ L/mol and 4.6×10³ L/mol， respectively. Specially， PI?m?OH has the ability to respond to Fe³⁺ within 2 min， which is much quicker than that of PI?o?OH. Furthermore， the coordination constant K_ass between PI?m?OH and Fe³⁺ is 3.82×10⁴ L/mol and higher than that of PI?o?OH， which means that PI?m?OH has better stabilities of coordination with Fe³⁺. The complexation ratio between two compounds and Fe³⁺ is determined by HRMS and Job's curves， based on which the structures for PI?m?OH-Fe³⁺ and PI?o?OH-Fe³⁺ are proposed. Besides， both isomeric probes could quantitatively detect the concentration of Fe³⁺ in real water sample by the fluorescence method， indicating that they have potential application in analyzing Fe³⁺ .

Key words: Phenanthro［9，10-d］imidazole, Isomerization, Distinguishable recognition, Iron（Ⅲ）, Real water sample, Complex ratio

CLC Number:

O657.3

Jing-Hui WEN, Bing ZHAO, Wei KAN, Li-Yan WANG, Li SUN, Tian-Shu SONG, Bo SONG. Synthesis of Isomers of Distinguishable Iron（Ⅲ） Fluorescent Probes and Application in Water Samples[J]. Chinese Journal of Applied Chemistry, 2022, 39(5): 787-796.

Figures/Tables 10

Fig.1 UV-Vis absorption spectra of PI?o?OH （1.0×10-5 mol/L）（A） and PI?m?OH（1.0×10-5 mol/L）（B） in presence of different metal ions （5.0×10-5 mol/L）

Fig.2 Fluorescence spectra of PI?o?OH（1.0×10-5 mol/L）（A） and PI?m?OH（1.0×10-5 mol/L）（B） in presence of different metal ions （5.0×10-5 mol/L）

Fig.3 Fluorescence spectral histograms of PI?o?OH （1.0×10-5 mol/L）（A） and PI?m?OH （1.0×10-5 mol/L）（B） to recognize Fe3+ （5.0×10-5 mol/L） in presence of other interference metal ions （5.0×10-4 mol/L）

Fig.4 The changes of the fluorescence emission spectra of PI?o?OH （1.0×10-5 mol/L）（A） and PI?m?OH （1.0×10-5 mol/L）（B） with the various pH value （3~12） in the absence and presence of Fe3+（5.0×10-5 mol/L）

Fig.5 Fluorescence spectra （A， C） and linear relation （B， D） of PI?o?OH （1.0×10-5 mol/L） and PI?m?OH （1.0×10-5 mol/L） with the increasing concentration of Fe3+ （0~200 μmol/L and 0~100 μmol/L）

Fig.6 Changes of fluorescence intensities of PI?o?OH （1.0×10-5 mol/L）（A） and PI?m?OH（1.0×10-5 mol/L）（B） with the increasing response times （ 0~10 min） before and after the addition of Fe3+ （5.0×10-5 mol/L）

Fig.7 HRMS （A. PI?m?OH；B. PI?m?OH?Fe3+） and Job's curve （C） for compounds PI?o?OH before and after the recognizing towards Fe3+

Fig.8 Structures of complexs PI?o?OH?Fe3+ and PI?m?OH?Fe3+

Table 1 Detection results of Fe 3+ in real water samples using compounds PI?o?OH and PI?m?OH

化合物 Compound	水样 Water sample	加入Fe³⁺ Add Fe³⁺/（μmol·L^-1）	检出Fe³⁺ Fe³⁺ detected/（μmol·L^-1）	回收率 Recovery rate/%	偏差 Deviation/%
PI?o?OH	自来水 Tap water	10	9.87	98.7	2.49
		50	50.14	100.3	2.81
		100	100.39	100.4	1.33
	湖水 Lake water	10	9.85	98.5	3.75
		50	50.08	100.2	1.68
		100	99.73	99.7	1.92
	河水 River water	10	10.31	103.1	0.29
		50	49.85	99.7	0.57
		100	100.51	100.5	1.13
PI?m?OH	自来水 Tap water	10	9.43	94.3	1.64
		50	52.79	105.6	3.07
		100	102.93	102.9	0.67
	湖水 Lake water	10	10.32	103.2	3.44
		50	49.08	98.2	3.96
		100	99.28	99.3	2.85
	河水 River water	10	10.14	101.4	0.35
		50	50.13	100.3	0.52
		100	99.83	99.8	1.21

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Synthesis of Isomers of Distinguishable Iron（Ⅲ） Fluorescent Probes and Application in Water Samples

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