Surface wettability and emission behavior tuned via solvent in a supramolecular self-assembly system based on a naphthalene diimides derivative

Cao, Xinhua; Li, Yiran; Zhang, Xiaoyuan; Gao, Aiping; Xu, Ruixiang; Yu, Youming; Hei, Xiaohan

doi:10.1016/j.apsusc.2019.144256

Cited by 12 publications

(6 citation statements)

References 49 publications

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“…Surface wettability was an important property for surface functional materials, which were applied in many fields, such as industry, agriculture and food industry. For self-assembled systems, molecules could self-assemble into nanostructures with different roughness in different solvents, even if the same molecule and different wettability surfaces can be conveniently constructed [ 63 ]. The surface wettability of material was measured by the measurement of the water contact angle.…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Quinoline-Based Supramolecular Gel for Selective and Ratiometric Sensing Zinc Ion with Multi-Modes

Qin

Wang

Gao

et al. 2022

Gels

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A gelator 1 containing functional quinoline and Schiff base groups that could form organogels in DMF, DMSO, acetone, ethanol and 1,4-dioxane was designed and synthesized. The self-assembly process of geator 1 was characterized by field emission scanning electron microscopy (FESEM), UV-vis absorption spectroscopy, fluorescence emission spectroscopy, Fourier transform infrared spectroscopy(FTIR), X-ray powder diffraction (XRD) and water contact angle. Under non-covalent interactions, gelator 1 self-assembled into microbelts and nanofiber structures with different surface wettability. Weak fluorescence was emitted from the solution and gel state of 1. Interestingly, gelator 1 exhibited good selectivity and sensitivity towards Zn2+ in solution and gel states along with its emission enhancement and change. The emission intensity at 423 nm of solution 1 in 1,4-dioxane was slightly enhanced, and a new emission peak appeared at 545 nm along with its intensity sequentially strengthened in the titration process. The obvious ratiometric detection process was presented with a limit of detection (LOD) of 5.51 μM. The detection mechanism was revealed by a theoretical calculation and NMR titration experiment, which was that Zn2+ induced the transition from trans- to cis- of molecule 1 and further coordinated with 1. This study will introduce a new method for the construction of functional self-assembly gel sensors for the detection of Zn2+.

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Section: Resultsmentioning

confidence: 99%

Fluorescent Quinoline-Based Supramolecular Gel for Selective and Ratiometric Sensing Zinc Ion with Multi-Modes

Qin

Wang

Gao

et al. 2022

Gels

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“…Furthermore, given the planar NI structure, the assembly of the organogelator molecules is assumed to adopt a J-type aggregation. [27,40] Temperature-dependent 1…”

Section: Uv-vis Testmentioning

confidence: 99%

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

et al. 2022

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The development of low molecular‐weight gelators for the construction of stimuli‐responsive gels is increasing attention because of the great application potential. In this work, we report the design and synthesis of two new naphthalimide derivatives, GSSN and GN, as supramolecular organogelators. GSSN contains a disulfide bond in the molecule, while GN contains no disulfide bond. As a result, only GSSN exhibited reduction responsiveness. A series of tests, including UV‐vis, temperature‐dependent 1H NMR, XRD, and SEM, were carried out to characterize the gelation capability and probe into the gelation mechanism. Results showed that GN can gelate more organic solvents than GSSN. Both hydrogen bonding and π stacking contribute to the gelation. Due to the difference in the assembly of the organogelator molecules, the organogels formed by GSSN and GN presented distinct morphologies. Moreover, strong hydrophobicity was found in the organogel films of GSSN and GN, suggesting potential application as hydrophobic coating materials.

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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.

Self Cite

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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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Surface wettability and emission behavior tuned via solvent in a supramolecular self-assembly system based on a naphthalene diimides derivative

Cited by 12 publications

References 49 publications

Fluorescent Quinoline-Based Supramolecular Gel for Selective and Ratiometric Sensing Zinc Ion with Multi-Modes

Fluorescent Quinoline-Based Supramolecular Gel for Selective and Ratiometric Sensing Zinc Ion with Multi-Modes

Gallic‐Acid‐Modified Naphthalimide Containing Disulfide Bond as Reduction‐Responsive Supramolecular Organogelator

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

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