A fluorescent non-conventional organogelator with gelation-assisted piezochromic and fluoride-sensing properties

Li, Ruohan; Wang, Sa; Li, Qian; Lan, Haichuang; Xiao, Shuzhang; Li, Yaqian; Tan, Ronghua; Yi, Tao

doi:10.1016/j.dyepig.2016.10.004

Cited by 66 publications

(14 citation statements)

References 47 publications

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“…The CGC is found to be 1.5 mg/mL (1.85 mM) in cyclohexane with the gel‐sol transition temperature of 48 °C. For comparison, the CGC is 3.03 mM in cyclohexane for ADPI molecule . ADIPA could not gelate any conventional solvents under the tested conditions.…”

Section: Methodsmentioning

confidence: 87%

“…Recently, we found that a low molecular weight compound with rigid structure ( ADPI in Scheme S1) could well gelate cyclohexane and mixed solvents containing cycloxhexane. The synergistic effect of intermolecular π‐π stacking and hydrogen‐bonding between imidazole rings are ascribed to the main driving forces . In order to explore more efficient gelators with low critical gelation concentration (CGC), we suppose that introducing stronger π‐π interactions might be one effective method.…”

Section: Methodsmentioning

confidence: 99%

“…With temperature increasing, all the peaks become sharper, manifesting a better resolution aroused by interruption of the strong intermolecular interactions in the gel state. It needs to note that the chemical shift of active proton (δ 8.92 ppm) on imidazole does not change with temperature, indicating that the hydrogen‐bonding between imidazole is not a driving force for the gelation of Br‐ADIPA molecules, which is quite different as that found in ADPI gel . In fact, most peaks are almost constant with temperature, except the resonance peak at 7.22 ppm, ascribed to the protons on triphenylamine groups.…”

Section: Methodsmentioning

confidence: 99%

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Halogen Effect on Non-Conventional Organogel Assisted by Balanced π-π Interaction

Lan

et al. 2017

ChemistrySelect

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Triphenylamine-functionalized anthracene derivatives bearing no alkyl chains or amide units (ADIPA and Br-ADIPA) are synthesized in a straightforward manner. Among these two compounds, Br-ADIPA could form stable gel in organic solvents, but ADIPA cannot gelate any conventional solvents under the tested conditions. In order to disclose the supramolecular self-assembly of Br-ADIPA gel, a series of characterizations were performed, which indicated that it might self-assemble into aggregates which do not involve p-p stacking between anthracene chromophore in the gel state, and intermolecular p-p interactions between phenyl rings on triphenylamine moieties are essential driven forces for its gelation. Interestingly, the self-assemblies of these two compounds calculated using Polymorph software well matched the characterization results. It revealed that a one-dimensional molecular packing was promoted by multiple intermolecular pp interactions between triphenylamine units in Br-ADIPA, and the bromine atom played important role in its balanced intermolecular p-p interactions. In comparison, these supramolecular forces in ADIPA provided a three-dimensional structure.Supramolecular gels are a class of soft materials involving reversible formation of nanoscale networks with the aid of noncovalent interactions, among which low-molecular-weight gels (LMWGs) have been paid great attention due to their potential applications in catalysis, [1] pollutant removal, [2] chemosensing, [3] energy transfer, [4] field-effect transistors [5] and drug delivery. [6]

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Section: Methodsmentioning

confidence: 87%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Halogen Effect on Non-Conventional Organogel Assisted by Balanced π-π Interaction

Lan

et al. 2017

ChemistrySelect

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“…Small organic fluorophores are indispensible tools for the construction of fluorescent probes because of the controllable optical properties such as bodipy, coumarin, rhodamine, fluorescein, etc . Among them, fluorophores derived from benzothiazole are widely used as the dye platform for designing of fluorescent probes .…”

Section: Introductionmentioning

confidence: 99%

A Light‐Up Fluorescent Probe for Detection of Formaldehyde in Serum and Gaseous Based on d‐PeT Process

et al. 2019

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A new Light‐Up fluorescent probe (FA‐P) for detection of formaldehyde was designed and synthesized based on the donor‐excited photo induced electron transfer (d‐PeT) process. The probe FA‐P was constructed by integrating a benzothiazole derivatives as the fluorescent skeleton and homoallylamino group as the specific recognition site. It showed the unique advantages of easy‐preparation, and excellent selectivity response toward formaldehyde. Besides, The probe FA‐P can not only detect formaldehyde gas through the prepared test paper, but also detect formaldehyde in serum solution.

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“…Many groups have made substantial efforts to design and synthesize optical sensors of fluoride ion in recent years [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. Among these optical sensors, imidazole-based optical sensors have been extensively investigated because these sensors are easily obtained and exhibit distinctive fluorescence property and strong interaction between N–H fragment and fluoride ion [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bisimidazole Derivatives for Selective Sensing of Fluoride Ion

Zhang

Liu

2017

Molecules

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Rapid and efficient analysis of fluoride ion is crucial to providing key information for fluoride ion hazard assessment and pollution management. In this study, we synthesized one symmetrical structure called 1,4-bis(4,5-diphenyl-1H-imidazol-2-yl)benzene (1a) and two asymmetrical structures, namely 2-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl)-1H-phenanthro(9,10-d)imidazole (1b) and 2-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl)-1H-imidazo(4,5-f)(1,10)phenanthroline (1c), which served as an efficient anion sensor for fluoride ion over a wide range of other anions (Cl−, Br−, I−, NO3−, ClO4−, HSO4−, BF4−, and PF6−) owing to imidazole group in the main backbone. The absorption intensity of compound 1a at λmax 358 nm slightly decreased; however, a new band at λmax 414 nm appeared upon the addition of fluoride ion, while no evident change occurred upon the addition of eight other anions. The photoluminescence intensity of compound 1a at λmax 426 nm was nearly quenched and fluorescence emission spectra were broadened when fluoride ion was added into dimethyl sulfoxide (DMSO) solution of compound 1a. Compared with the optical behaviors of the DMSO solution of compound 1a in the presence of Bu4N+F−, compounds 1b and 1c exhibited considerable sensitivity to fluoride ion due to the increase in coplanarity. Furthermore, compared with the fluorescence emission behaviors of the DMSO solutions of compounds 1a and 1b in the presence of Bu4N+F−, compound 1c exhibited the most significant sensitivity to fluoride ion due to the charge transfer enhancement. Consequently, the detection limits of compounds 1a–1c increased from 5.47 × 10−6 M to 4.21 × 10−6 M to 9.12 × 10−7 M. Furthermore, the largest red shift (75 nm) of the DMSO solution compound 1c in the presence of fluoride ion can be observed. Our results suggest that the increase in coplanarity and the introduction of electron-withdrawing groups to the imidazole backbone can improve the performance in detecting fluoride ion.

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A fluorescent non-conventional organogelator with gelation-assisted piezochromic and fluoride-sensing properties

Cited by 66 publications

References 47 publications

Halogen Effect on Non-Conventional Organogel Assisted by Balanced π-π Interaction

Halogen Effect on Non-Conventional Organogel Assisted by Balanced π-π Interaction

A Light‐Up Fluorescent Probe for Detection of Formaldehyde in Serum and Gaseous Based on d‐PeT Process

Synthesis of Bisimidazole Derivatives for Selective Sensing of Fluoride Ion

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