A bis-naphthalimide functionalized pillar[5]arene-based supramolecular π-gel acts as a multi-stimuli-responsive material

Zhang, Youming; Li, Yongfu; Zhong, Kai-Peng; Qu, Wenjuan; Yao, Hong; Wei, Tai‐Bao; Lin, Qi

doi:10.1039/c8nj03583k

Cited by 20 publications

(13 citation statements)

References 57 publications

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“…Recently, supramolecular self‐assembly by reversible noncovalent interactions not only exhibiting the properties of traditional polymers but also presenting new structures and functions, has attracted much attention because of its sensitivity to external stimuli (chemicals, heat and p H) [7–12] . In addition, supramolecular assemblies have become a wonderful candidate for a class of new stimuli‐responsive materials as well as chemosensors [13–20] …”

Section: Introductionmentioning

confidence: 99%

Stimuli‐Responsive Complexation Based on Twisted Cucurbit[14]uril and p‐Diaminoazobenzene

et al. 2022

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The supramolecular assembly between twisted cucurbit[14]uril (tQ[14]) and p‐diaminoazobenzene (DAAB) has been successfully developed based on host‐guest interactions. Interestingly, as the temperature increases, the assembly dissociates and recovers when the temperature decreases. This shows that the association and dissociation of the supramolecular assembly can be reversibly controlled by the temperature. In addition, the tQ[14]‐DAAB complex also exhibits selective ultraviolet and colorimetric responses for AcO− and F−, the detection limits of the sensor for AcO− and F− are 5.17×10−6 M and 2.31×10−5 M, respectively. The tQ[14]‐DAAB exhibits potential analysis applications.

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Section: Introductionmentioning

confidence: 99%

Stimuli‐Responsive Complexation Based on Twisted Cucurbit[14]uril and p‐Diaminoazobenzene

et al. 2022

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“…Of the various LMWG systems, molecules with rigid aromatic conjugates [21] have been well exploited for the fabrication of stimuli‐responsive gels. With respect to the aromatic unit, naphthalimide (NI) is a planar π‐conjugated chromophore providing strong π interactions and tunable photophysical properties and thus is often involved in the design of sensitive LMWGs [22] . Particularly, NIs are modified with long hydrophobic chains to render gelation in organic solvents, forming organogels [23] .…”

Section: Introductionmentioning

confidence: 99%

“…With respect to the aromatic unit, naphthalimide (NI) is a planar π-conjugated chromophore providing strong π interactions and tunable photophysical properties and thus is often involved in the design of sensitive LMWGs. [22] Particularly, NIs are modified with long hydrophobic chains to render gelation in organic solvents, forming organogels. [23] NI-derived organogels displaying discernible signal outputs have been extensively investigated as stimuli-responsive chemosensors.…”

Section: Introductionmentioning

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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“…Cao’s group synthesized a new fluorescent organogelator and achieved continuous, instant, and visual multichannel sensing of volatile acid and organic amine gases . However, the examples of fluorescent low-molecular-weight organogelators with stimuli-responsive properties are mainly focused on single stimulus-response property. − Integrating multiple responsive properties into a single organogelator to achieve multistimuli-responsive properties of a single molecule has always been of interest to the researchers. , However, reports on multistimuli response of a fluorescent low-molecular-weight organogelator are relatively few, ,− especially those with both mechanofluorochromic and acidochromic properties. As far as we know, there are only two such examples so far.…”

Section: Introductionmentioning

confidence: 99%

Multistimuli-Responsive Fluorescent Organogelator Based on Triphenylamine-Substituted Acylhydrazone Derivative

et al. 2020

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A new triphenylamine-based acylhydrazone derivative (TPAH-B8) was synthesized. TPAH-B8 could form organogels in cyclohexane through ultrasonic treatment. A typical gelation-induced fluorescence enhancement property was observed, which was attributed to the formation of J-aggregate in the gel state. More interestingly, TPAH-B8 exhibited multistimuli responsive behaviors. First, TPAH-B8 showed a solvatochromic effect, with the emission color changing from blue to cyan with the change in solvent from nonpolar cyclohexane to polar dimethyl sulfoxide (DMSO). Second, TPAH-B8 showed a reversible mechanofluorochromism. The xerogel of TPAH-B8 emitted a blue fluorescence, while the fluorescence color changed to cyan after grinding. The cyan and blue colors could be repeated with the treatment of grinding and annealing, which was explored and ascribed to the transformation between crystalline and amorphous states. Third, TPAH-B8 revealed acidochromic property. The fluorescence color of TPAH-B8 in organogel and solid states could be switched by trifluoroacetic acid (TFA)/triethylamine (TEA). This work not only demonstrated the multistimuli-responsive fluorescent properties of TPAH-B8 but also offered an easy way to develop new kinds of multistimuli-responsive fluorescent materials.

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A bis-naphthalimide functionalized pillar[5]arene-based supramolecular π-gel acts as a multi-stimuli-responsive material

Abstract: A novel approach for the design of multi-stimuli-responsive supramolecular functional materials was successfully developed by introducing the competition of π–π stacking and cation–π interactions into a pillar[5]arene-based supramolecular π-gel (MP5-G).

Cited by 20 publications

References 57 publications

Stimuli‐Responsive Complexation Based on Twisted Cucurbit[14]uril and p‐Diaminoazobenzene

Stimuli‐Responsive Complexation Based on Twisted Cucurbit[14]uril and p‐Diaminoazobenzene

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

Multistimuli-Responsive Fluorescent Organogelator Based on Triphenylamine-Substituted Acylhydrazone Derivative

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