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

doi:10.6023/cjoc202010018

Abstract

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

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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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Fig. & Tab. 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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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