Switching in visible-light emission of carbazole-modified pyrazole derivatives induced by mechanical forces and solution-organogel transition

Sun, Meng; Zhai, Lu; Sun, Jingbo; Zhang, Fushuang; Mi, Wenhua; Ding, Jipeng; Lu, Ran

doi:10.1016/j.dyepig.2018.10.005

Cited by 14 publications

(7 citation statements)

References 73 publications

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“…More specifically, representative AIE‐active LMWGs based on 1,8‐naphthalimide are 125 , 126 , 127 and 129 , [ 130 ] 128 , [ 131 ] 130 , [ 132 ] and 131 and 132 . [ 133 ] Representative AIE‐active LMWGs based on carbazole are 133 and 139 , [ 134 ] 134 , 135 , 136 and 137 , [ 135 ] 138 , [ 136 ] 140 , [ 137 ] and 141 , [ 138 ] while representative AIE‐active LMWGs based on trimesic amides, are 142 , [ 139 ] 143 , [ 140 ] 144 , [ 141 ] 145 , [ 142 ] and 146 . [ 143 ] Moreover, representative AIE‐active LMWGs based on heterocycles and other non‐typical chromophores are 147 , [ 144 ] 148 , 149 and 150 , [ 145 ] 151 , [ 146 ] 152 , [ 147 ] 153 , [ 148 ] 154 , 155 and 156 , [ 149 ] 157 , [ 150 ] 158 , [ 151 ] 159 , 160 , 161 and 162 , [ 152 ] 163 , 164 and 165 , [ 153 ] 166 , 167 , 168 and 169 , [ 154 ] 170 , [ 155 ] 171 , [ 156 ] 172 , [ 157 ] and 173 .…”

Section: Fabricationsmentioning

confidence: 99%

Aggregation‐Induced Emission‐Active Gels: Fabrications, Functions, and Applications

Xie

et al. 2021

Advanced Materials

142

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Chromophores that exhibit aggregation‐induced emission (i.e., aggregation‐induced emission luminogens [AIEgens]) emit intense fluorescence in their aggregated states, but show negligible emission as discrete molecular species in solution due to the changes in restriction and freedom of intramolecular motions. As solvent‐swollen quasi‐solids with both a compact phase and a free space, gels enable manipulation of intramolecular motions. Thus, AIE‐active gels have attracted significant interest owing to their various distinctive properties and promising application potential. Herein, a comprehensive overview of AIE‐active gels is provided. The fabrication strategies employed are detailed, and the applications of AIEgens are summarized. In addition, the gel functions arising from the AIE moieties are revealed, along with their structure–property relationships. Furthermore, the applications of AIE‐active gels in diverse areas are illustrated. Finally, ongoing challenges and potential means to address them are discussed, along with future perspectives on AIE‐active gels, with the overall aim of inspiring research on novel materials and ideas.

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Section: Fabricationsmentioning

confidence: 99%

Aggregation‐Induced Emission‐Active Gels: Fabrications, Functions, and Applications

Xie

et al. 2021

Advanced Materials

142

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“…For example, it was only 3.73% in cyclohexane and 23.28% in DMSO, showing a negative solvatokinetic effect. 23,41 2.2. Study on Electronic-State Transitions and Frontier Molecular Orbitals.…”

Section: Resultsmentioning

confidence: 99%

“…Some of the compounds exhibited gelation-induced fluorescence enhancement properties, and these organogelators exhibited reversible mechanofluorochromic behavior under the treatment of grinding/fuming with CH 2 Cl 2 . 23 Yi's group studied a series of organogelators based on naphthalimide which possess mechanofluorochromic behaviors, and these organogelators were used to sense low pressures in the range of 2−40 MPa with a fluorescent signal output. 24 Furthermore, the reports on the detection of acid by the multichannel response characteristics of the orgnaogelators have attracted much attention in recent years.…”

Section: Introductionmentioning

confidence: 99%

“…For example, Lu’s group synthesized a series of carbazole-modified pyrazole derivatives. Some of the compounds exhibited gelation-induced fluorescence enhancement properties, and these organogelators exhibited reversible mechanofluorochromic behavior under the treatment of grinding/fuming with CH 2 Cl 2 . Yi’s group studied a series of organogelators based on naphthalimide which possess mechanofluorochromic behaviors, and these organogelators were used to sense low pressures in the range of 2–40 MPa with a fluorescent signal output .…”

Section: Introductionmentioning

confidence: 99%

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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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“…In order to generate wholly functional organic nanostructures the design of fully conjugated organogelators is essential . Up to date, the non‐traditional organogelators in absence of the above gelation units have been synthesized, including dehydrobenzoannulenes bearing methyl ester groups, discotic hexaazatritriphenylene with six aromatic moieties, trifluoromethyl modified cyanostilbene, salicylaldimine derivatives with terminal CF 3 groups, tert ‐butyl carbazole derivatives . On the other hand, the design of spiro compounds offers a simple strategy to fabricate the multi‐dimensional nanostructures of organic semiconductors due to their nonplanar configuration.…”

Section: Introductionmentioning

confidence: 99%

Spirofluorene‐Cored Difluoroboron β‐Diketonate Complexes with Terminal Carbazole: Synthesis, Self‐Assembling, and Fluorescent Sensory Properties

et al. 2019

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Spirofluorene‐cored bis(difluoroboron β‐diketonate) complexes bearing terminal carbazoles (CbzBSF) and tert‐butylcarbazoles (TCbzBSF) have been synthesized. It was found that only TCbzBSF could form organogels in cyclohexane and methylcyclohexane, suggesting that tert‐butylcarbazole was essential for its organogelation directed by weak π–π interactions. It is worth noting that TCbzBSF could entrap ca. 5800 molecules of methylcyclohexane per gelator molecule, so this fully conjugated complex without traditional gelation group could be considered as a supergelator. The gained organogel showed reversible thixotropic and temperature‐dependent sol‐gel transitions. In particular, the orange red fluorescence of the xerogel‐based film of TCbzBSF could be quenched when exposed to gaseous aromatic amines of aniline, N‐methylaniline, and N,N‐dimethylaniline. The detection limit for aniline vapor of the xerogel‐based film was as low as 0.56 ppb.

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Switching in visible-light emission of carbazole-modified pyrazole derivatives induced by mechanical forces and solution-organogel transition

Cited by 14 publications

References 73 publications

Aggregation‐Induced Emission‐Active Gels: Fabrications, Functions, and Applications

Aggregation‐Induced Emission‐Active Gels: Fabrications, Functions, and Applications

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

Spirofluorene‐Cored Difluoroboron β‐Diketonate Complexes with Terminal Carbazole: Synthesis, Self‐Assembling, and Fluorescent Sensory Properties

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