基于聚集诱导发光的水杨醛酰腙衍生物的力致荧光变色和Al3+检测性质研究

doi:10.6023/cjoc202010018

摘要/Abstract

设计合成了一种基于水杨醛的酰腙衍生物(Z)-N'-[4-(二乙基胺基)-2-羟基苯亚甲基]苯甲酰肼(DHBH). 该化合物不仅表现出优良的聚集诱导发光(AIE)性能, 而且表现出可逆的力致荧光变色性能. 粉末X射线衍射和场发射扫描电镜结果表明, 该DHBH在外界压力刺激下发生力致荧光变色性能的原因是其晶态与无定形态之间的相互转化. 此外, DHBH可以选择性地识别铝离子, 并且显示出很好的抗干扰性, 对铝离子的荧光分析检测限为4.01×10^–9 mol/L.

关键词: 力致荧光变色, 聚集诱导发光, 铝离子, 酰腙

In this work, a versatile salicylaldehyde-based acylhydrazone compound (Z)-N'-(4-(diethylamino)-2-hydroxy- benzylidene)benzohydrazide (DHBH) has been designed and easily synthesized. And it not only showed aggregation-induced emission (AIE), but also reversible mechanochromic luminescence. The results of powder X-ray diffraction (PXRD) and field emission scanning electron microscopy (FESEM) revealed that the mechano?uorochromic (MFC) mechanism was the transformation between ordered crystalline and amorphous states upon external stimuli. In addition, compound DHBH displayed selective turn-on fluorescence with Al³⁺ and the probe exhibited good response and anti-interference performance. The detection limit for Al³⁺ was calculated to be about 4.01×10^–9 mol/L.

Key words: mechano?uorochromic luminescence, aggregation-induced emission, aluminium ion, acylhydrazone

引用此文

贾俊辉, 温娟娟. 基于聚集诱导发光的水杨醛酰腙衍生物的力致荧光变色和Al³⁺检测性质研究[J]. 有机化学, 2021, 41(4): 1728-1733.

Junhui Jia, Juanjuan Wen. Mechanoﬂuorochromic Luminescence, and Al³⁺ Detection of an Aggregation-Induced Emission-Active Salicylaldehyde-Based Acylhydrazone Derivative[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1728-1733.

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图/表 8

Scheme 1. Synthetic route for DHBH.

Figure 1. (a) PL spectra of DHBH in THF/H2O mixtures solutions with different fw (c=1×10–5 mol/L), and (b) the emission intensity of DHBH at λ max with different fwin THF/H2O mixtures solutions Insert: the photos of DHBH in THF/H2O mixtures solution with different fw under 365 nm UV lamp

Figure 2. (a) Solid state emission spectra of DHBH in different states, and (b) powder wide-angle X-ray diffraction patterns of DHBH in different states at room temperature Inset: photographic images of DHBH in response to mechanical grinding and fuming with dichloromethane or heating under the irradiation of 365 nm UV light

Figure 3. FESEM images of DHBH in the states of pristine (a), grinding (b) and fuming with DCM (c) and THF(d).

Sample	τ_s^a/ns	α₁/%	τ₁^c/ns	α₂^b/%	τ₂^c/ns	α₂^b/%	α₃^b/%%	τ₂^c/ns	λ_em/nm	Φ_s
Pristine	3.75	97.07	0.01	2.50	1.19	0.42	0.42	7.38	457	0.25
Grinding	1.79	93.52	0.02	5.76	0.67	0.72	0.72	4.22	523	0.11

Table 1. Data for DHBH before and after being grinded.

Figure 4. (a) Molecular conformation of DHBH viewed along b-axis, (b) intermolecular interactions between molecules of adjacent columns along a-axis, and (c) the planforms of molecular stacking of DHBH viewed from c-axis Inset: fluorescent image of DHBH single crystal under UV light

Figure 5. (a) Fluorescence emission spectra and (b) color changes of DHBH (10 μmol?L –1) upon addition of 10 equiv. of various metal ions (K+, Cu2+, Co2+, Cd2+, Al3+, Zn2+, Ag+, Fe2+, Fe3+, Ni2+, Hg2+, Mn2+, Ca2+, and Na+) in DMSO solutions under 365?nm UV irradiation (λex=395 nm)

Figure 6. (a) Bar graph representing the change of the relative emission intensity of DHBH at 476 nm upon treatment with various metal ions (λex=395 nm); (b) competitive selectivity of DHBH-Al3+ (10 μm) in the presence of 10 equiv. of various anions (1) Blank, (2) K+, (3) Cu2+, (4) Co2+, (5) Cd2+, (6) Al3+, (7) Zn2+, (8) Ag+, (9) Fe2+, (10) Fe3+, (11) Ni2+, (12) Hg2+, (13) Mn2+, (14) Ca2+, (15) Na+

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基于聚集诱导发光的水杨醛酰腙衍生物的力致荧光变色和Al³⁺检测性质研究

Mechanoﬂuorochromic Luminescence, and Al³⁺ Detection of an Aggregation-Induced Emission-Active Salicylaldehyde-Based Acylhydrazone Derivative

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