Bis-naphthalimide-based supramolecular self-assembly system for selective and colorimetric detection of oxalyl chloride and phosgene in solution and gas phase

Wang, Qingqing; Wu, Huijuan; Gao, Aiping; Ge, Xuefei; Chang, Xue-Ping; Cao, Xinhua

doi:10.1016/j.cclet.2022.06.067

Cited by 17 publications

(6 citation statements)

References 46 publications

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“…Based on the coordination interaction of the pyridine group in molecule 1 and its AIE effect in a gel state, we tried to explore the responsive ability of the gel of 1 to different metal ions [ 68 , 69 , 70 , 71 ]. Fourteen common metal ions were selected in this experiment.…”

Section: Resultsmentioning

confidence: 99%

Bis-Pyridine-Based Organogel with AIE Effect and Sensing Performance towards Hg2+

Gao

Qin

Wang

et al. 2022

Gels

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A novel gelator (1) based on a bis-pyridine derivative was designed and synthesized, which could form stable gels in methanol, ethanol, acetonitrile, ethyl acetate, DMF/H2O (4/1, v/v) and DMSO/H2O (4/1, v/v). The self-assembly process of gelator 1 was studied by field emission scanning electron microscopy (FESEM), UV–vis absorption spectroscopy, fluorescence emission spectroscopy, Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction and a water contact angle experiment. Gelator 1 exhibited obvious AIE behavior. On the base of its AIE, the gel of 1 could detect Hg2+, which resulted in fluorescence quenching and a gel–sol transition. 1H NMR titration experiments with Hg2+ revealed that the metal coordination interaction induced the fluorescence quenching and the breakdown of the noncovalent interaction in the gel system. This research provides a new molecular mode for designing a functional self-assembly gel system.

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Section: Resultsmentioning

confidence: 99%

Bis-Pyridine-Based Organogel with AIE Effect and Sensing Performance towards Hg2+

Gao

Qin

Wang

et al. 2022

Gels

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“…Supramolecular self-assembly can proceed under the synergistic action of weak and reversible noncovalent interactions, such as hydrogen bonds, π–π stacking, van der Waals’ force, electrostatic interaction, and hydrophobicity effect. − According to the weakness and reversibility of noncovalent interactions, supramolecular self-assembly systems exhibit outstanding responses toward external stimuli, such as light, heat, electricity, magnetism, mechanical force, chemical substance, and biomolecules. − In other words, the self-assembly process can be finely adjusted by tuning the noncovalent interactions. We have previously reported that the self-assembly process of two gelators can be tuned by changing solvents and inducing variations in the emission properties, morphology, and surface wettability in solvents. , Low-molecular-weight organic molecular gels, as a kind of self-assembly soft matter, have received immense attention as they can be used for the fabrication of sensors, light-harvesting systems, drug delivery agents, and catalysis. They can also be used in the fields of pollution removal, bioimaging, and tissue engineering. − The high applicability of supramolecular gels can be attributed to their inherent three-dimensional network structure.…”

Section: Introductionmentioning

confidence: 99%

“…We have previously reported that the self-assembly process of two gelators can be tuned by changing solvents and inducing variations in the emission properties, morphology, and surface wettability in solvents. 38,39 Low-molecular-weight organic molecular gels, as a kind of selfassembly soft matter, have received immense attention as they can be used for the fabrication of sensors, light-harvesting systems, drug delivery agents, and catalysis. They can also be used in the fields of pollution removal, bioimaging, and tissue engineering.…”

Section: ■ Introductionmentioning

confidence: 99%

Robust Fluorescent Self-Assembly System for Sensing of Phosgene, Thionyl Chloride, and Oxalyl Chloride

Qin

Wang

Gao

et al. 2023

ACS Sustainable Chem. Eng.

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A self-assembly fluorescent gelator (DIAN) based on a 3,4-diamine-naphthalimide derivative was constructed for sensing of multiple hazardous substances. The gelator DIAN self-assembled into organogels to form tightly packed nanofiber morphologies with hydrophobicity (water contact angles in the range of 130–146°). DIAN responded to phosgene in a ratiometric mode, while it responded to thionyl chloride (SOCl2) and oxalyl chloride ((COCl)2) under the fluorescent “turn-off” mode. Results obtained from NMR and HRMS experiments demonstrated the sensing mechanism, and it was observed that phosgene, SOCl2, and (COCl)2 initially reacted with two amine groups of naphthalimide. The corresponding cyclization products were formed, and this induced the changes in fluorescence emission. Low limit of detection (LOD) values for phosgene, SOCl2, and (COCl)2 were recorded for DIAN in solution (LOD = 4.21, 1.98, and 1.29 nM) and xerogel films (LOD = 105, 69.1, and 33.3 ppb). The results reported herein can help provide a new platform for monitoring toxic phosgene, thionyl chloride, and oxalyl chloride.

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“…Through the rational design and the reversibility of the above noncovalent interaction, the desirable gels possess the sensitive responsive features to external stimuli. [25][26][27][28][29][30] Naphthalimide as a classical and versatile fluorescent molecule has been explored extensively owing to its unique photophysical properties. [31][32][33] It is simple and convenient to synthesize multifunctional naphthalimide derivative though the modifications at 3-or 4-site of the aromatic core with the multifarious structural units and functional groups.…”

Section: Introductionmentioning

confidence: 99%

Regulation of the supramolecular self‐assembly process by the number of 1, 8‐naphthalimide groups in the gelator

Wu,

Ma,

Gao

et al. 2023

ChemistrySelect

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Three naphthalimide‐based gelators (NE1,NE2, NE3) with corresponding one, two and three N‐undecanoic acid methylester‐1,8‐naphthalimide were designed and synthesized (the abbreviation NE1‐NE3, N assigned to the naphthalimide, E assigned to ester, and numerber representing the number of N‐undecanoic acid methylester‐1,8‐naphthalimide) The different number of 1, 8‐naphthalimide groups in gelator endowed them with the different central groups, conjugated structures and steric configurations, which could bring different self‐assembly abilities and behaivors. The self‐assembly processes of three gelators in different solvents were characterized by multiple characterization technologies. The gelation ability, self‐assembly structure, fluorescence emission behavior, material surface wettability of this system could be regulated by the number of 1, 8‐naphthalimide groups. Gelator NE1 possessed the best gelation ability among three gelators, and the self‐assembly structures in gels NE1 from different solvents were completely different from that of gels NE2 and NE3. In addition, surface wettability of film NE1 exhibited the highest hydrophobicity under the same condition. Fluorescence emission behavior of this system could be tuned by the number of 1, 8‐naphthalimide groups solvent and gel state. At the same condition, the absorbance at the same band was gradually decreased with the number of 1, 8‐naphthalimide groups increasing. This work will provide a new design way for construction of functional supramolecular self‐assembly process.

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Bis-naphthalimide-based supramolecular self-assembly system for selective and colorimetric detection of oxalyl chloride and phosgene in solution and gas phase

Cited by 17 publications

References 46 publications

Bis-Pyridine-Based Organogel with AIE Effect and Sensing Performance towards Hg2+

Bis-Pyridine-Based Organogel with AIE Effect and Sensing Performance towards Hg2+

Robust Fluorescent Self-Assembly System for Sensing of Phosgene, Thionyl Chloride, and Oxalyl Chloride

Regulation of the supramolecular self‐assembly process by the number of 1, 8‐naphthalimide groups in the gelator

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