A Water-Soluble Naphthalimide-Based Fluorescent Probe for Specific Sensing of Fe3+ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$

doi:10.6023/cjoc202204032

Abstract

N-(2-(2-(2-Hydroxyethoxy)ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)furan-2-carboxamide (1) that can selectively recognize Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ was synthesized, which was the first small molecule probe based on naphthalimide to detect $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$. The pH titration showed that the spectral red shift caused by the enhancement of intramolecular charge transfer (ICT) effect was as a result of formation of amide anion. Besides, the selectivity, concentration titration, time dependence, quenching constant, detection limit and recognition mechanism of probe 1 to Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ were also studied in CH₃CN/N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid (HEPES) buffer solution. The results showed that Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ could rapidly quenched the fluorescence of probe 1 through the inner filter effect. The quenching effects remained constant after 30 s, and the quenching constants were 6.14×10³ and 6.55×10³ L•mol^–1, respectively. The detection limits of probe 1 for Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ were 1.62 and 1.56 μmol/L, respectively. The determination of Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ in water samples made it clear that probe 1 could be used as a potential detection tool in practical application.

Key words: fluorescent probe, $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$, Fe³⁺, naphthalimide, inner filter effect

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Chuntian Shi, Mei Yu, Aibin Wu, Jiangxiong Luo, Xiaojun Li, Ningchen Wang, Wenming Shu, Weichu Yu. A Water-Soluble Naphthalimide-Based Fluorescent Probe for Specific Sensing of Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2806-2813.

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Fig. & Tab. 11

Scheme 1. Synthesis of probe 1 Reagents and conditions: (a) 2-(2-aminoethoxy)ethanol, DMF, 150 ℃; (b) furoyl chloride, Et3N, CH3CN, 90 ℃.

Figure 1. (a) Fluorescence spectra of probe 1 (10 μmol/L, CH3CN/H2O, V∶V=1∶9) under different pH and (b) curves between fluorescence intensity of probe 1 at 463 nm and different pH values

Scheme 2. Response mechanism of spectra of probe 1 under strong basic conditions

Figure 2. Fluorescence spectra of probe 1 in CH3CN/HEPES (V∶V=1∶9, 10 mmol/L, pH=7.4) buffer solution upon addition of Pb2+, Na+, Ba2+, Sn2+, Cd2+, Co2+, Ag+, Cr3+, Mn2+, Ni2+, Fe3+, K+, Ca2+, Hg2+, Zn2+, Al3+, Cu2+, Mg2+ and Fe2+ ions

Figure 3. (a) Fluorescence titration spectra of probe 1 in CH3CN/HEPES (V∶V=1∶9, 10 mmol/L, pH=7.4) buffer solution upon addition of Fe3+ and (b) curves between fluorescence intensity of probe 1 at 463 nm and different Fe3+ concentration

Figure 4. Absorption spectra of probe 1 and Fe3+ and the fluorescence spectrum probe 1 in CH3CN/HEPES (V∶V=1∶9, 10 mmol/L, pH=7.4) buffer solution.

Figure 5. Fluorescence emission spectra of probe 1 in CH3CN/HEPES (V∶V=1∶9, 10 mmol/L, pH=7.4) buffer solution upon addition of $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$, ${{\text{S}}_{2}}\text{O}_{5}^{2-}$, CH3COO–, ClO–, $\text{NO}_{3}^{-}$, $\text{CO}_{3}^{2-}$, Br–, $\text{HCO}_{3}^{-}$, ${{\text{H}}_{2}}\text{PO}_{4}^{-}$, Cl–, ${{\text{S}}_{2}}\text{O}_{3}^{2-}$, $\text{HSO}_{3}^{-}$, $\text{ClO}_{3}^{-}$, I–, $\text{SO}_{4}^{2-}$ and $\text{NO}_{2}^{-}$ ions

Figure 6. (a) Fluorescence titration spectra of probe 1 in CH3CN/HEPES (V∶V=1∶9, 10 mmol/L, pH=7.4) buffer solution upon addition of $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ and (b) curves between fluorescence intensity of probe 1 at 463 nm and different $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ concentration

Figure 7. Absorption spectra of probe 1 and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$, and the fluorescence spectrum of probe 1 in CH3CN/HEPES (V∶V=1∶9, 10 mmol/L, pH=7.4) buffer solution

Figure 8. Discrimination of Fe3+ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ and the reversibility of probe 1 assisted by EDTA

Tested ion	Ion added/ (μmol•L^–1)	Ion found/ (μmol•L^–1)	Recovery/%	RSD/%
Fe³⁺	2.00	2.13	106.50	3.30
	5.00	5.20	104.00	1.01
	10.00	10.34	103.40	1.97
$\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$	2.00	1.98	99.00	2.31
	5.00	5.01	100.20	1.94
	10.00	9.99	99.90	0.99

Table 1. Determination of Fe3+ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$ in water samples (n=5).

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水溶性萘酰亚胺类荧光探针对Fe³⁺和$\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的特异性检测

A Water-Soluble Naphthalimide-Based Fluorescent Probe for Specific Sensing of Fe³⁺ and $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$

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水溶性萘酰亚胺类荧光探针对Fe3+和$\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$的特异性检测