Effective structural modification of traditional fluorophores to obtain organic mechanofluorochromic molecules

Huang, Xiaobo; Qian, Lebin; Zhou, Yibin; Liu, Miaochang; Cheng, Yixiang; Wu, Huayue

doi:10.1039/c8tc00043c

Cited by 132 publications

(57 citation statements)

References 102 publications

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“…After this ground-breaking work, assembly-or aggregation-induced enhancement of CPL has been reported in various nanomaterial system, including platinum(II) complexes, [117,118] chiral binaphthyl derivatives, [119] polymers, [114,[120][121][122][123] leucine-and valine-containing luminophores, [124,125] perylene bisimides, [126,127] and so on. [26,128]…”

Section: Assembly/aggregation-enhanced Cplmentioning

confidence: 99%

Circularly Polarized Luminescence in Nanoassemblies: Generation, Amplification, and Application

et al. 2019

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Yutao Sang obtained his B.Sc. and M.Sc. degrees in chemistry from Qingdao University, China. In 2016, he enrolled on a Ph.D. course at the Institute of Chemistry, Chinese Academy of Sciences (ICCAS), under the supervision of Prof. Minghua Liu, where he is currently in his third year. His ongoing research includes supramolecular chirality, chiroptical materials, and symmetry breaking of achiral molecules in gels and related systems. Pengfei Duan received his Ph.D. degree from the Institute of Chemistry, Chinese Academy of Sciences (CAS) in 2011 with Prof. Minghua Liu on chiral selfassembly in colloid and interface chemistry. He was a postdoctoral research fellow with Prof. Nobuo Kimizuka at Kyushu University, working on photon upconversion in self-assembled systems. In 2015, he became a professor at the National Center for Nanoscience and Technology (NCNST). His current research interests focus on photochemistry and photophysics in chiral supramolecular systems.

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Section: Assembly/aggregation-enhanced Cplmentioning

confidence: 99%

Circularly Polarized Luminescence in Nanoassemblies: Generation, Amplification, and Application

et al. 2019

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“…Measurements and materials 1 Ha nd 13 Cn uclear magnetic resonance (NMR) spectra were determined by using aB ruker DRX 500 NMR spectrometer with CDCl 3 as as olvent and trimethylsilane as ar eference. Elemental analyses (C, H, and N) were recorded by using an Elementar Vario MICRO analyzer.T he mass spectrum was determined by using aF innigan DECAX-30 000 LCQ Deca mass spectrometer.U ltraviolet-visible (UV/ Vis) absorption and fluorescence spectra were recorded by using a Cary 500 spectrometer and aH ITACHI F-4500 spectrophotometer, respectively.F luorescence quantum yields (F F )i nt he solid state and fluorescence lifetimes were obtained by using aF luoromax-4 spectrophotometer.S canning electron microscopy images were determined by using aJ EOL Model JSM-6360 SEM microscope.…”

Section: Methodsmentioning

confidence: 99%

“…In recent years, 1,4‐dihydropyridine‐based fluorescent molecules have received increasing attention because of their simple structures, easy syntheses, excellent photophysical properties, and extensive applications in fluorescent sensors . Importantly, some 1,4‐dihydropyridine derivatives reportedly exhibit outstanding AIE properties and emit good solid‐state fluorescence upon a simple structural modification.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, 1,4-dihydropyridine-based fluorescent molecules have received increasing attention because of their simple structures, easy syntheses, excellent photophysical properties, and extensive applications in fluorescent sensors. [12][13][14][15][16][17][18] Importantly,s ome1 ,4-dihydropyridined erivatives reportedly exhibit outstanding AIE properties and emit good solid-state fluorescenceu pon as imple structuralm odification. Specifically,anappropriate structuralunit introduced on the nitrogena tom of the 1,4-dihydropyridine ring can lead to twisted molecular conformations.…”

Section: Introductionmentioning

confidence: 99%

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Aggregation‐Induced Emission‐Active 1,4‐Dihydropyridine‐Based Dual‐Phase Fluorescent Sensor with Multiple Functions

Zhou

Chen

Duan

et al. 2019

Chemistry An Asian Journal

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A N‐2‐phenylethyl‐substituted 1,4‐dihydropyridine derivative (NDHP) containing 5,5‐dimethylcyclohexane‐1,3‐dione and naphthylethylene was designed and synthesized. NDHP acts as a multifunctional fluorescent sensor in dual phases. The crystal structure analysis confirms that the NDHP molecules have highly twisted conformations. The twisted conformation results in aggregation‐induced emission properties and solid‐state emission, by restricting the intramolecular free rotation in the aggregated or solid state. In the solid state, NDHP exhibits reversible mechanochromic properties as a result of the transition between the amorphous and crystalline states. NDHP also exhibits a rare phenomenon of acid‐fumed solid‐state emission enhancement owing to the change in packing mode from a zigzag arrangement to J‐aggregation. The solid‐state stimuli‐responsive fluorescence switching is applied to realize a rewritable optical recording media and a multiple output combinational logic system. In solution, NDHP shows a selective fluorescence response for environmentally harmful Hg2+, with a limit of detection of 2.7 nm. This results from the “turn‐on” responsive behavior owing to the Hg2+‐triggered aggregation of the NDHP molecules. NDHP is also used in the imaging of intracellular Hg2+ in HeLa cells. These findings provide a feasible and attractive route for developing multifunctional fluorescent sensors for use in dual phases.

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“…LSCEs can also be engineered to perform exactly the opposite task, that is, to encode mechanical inputs into optical signals. For this purpose, the intermolecular interactions established between the mesogenic molecules and rationally designed luminescent labels must be altered upon the application or release of a mechanical stimulus [11][12][13][14][15][16][17][18]. In this way, the introduction of selected organic fluorophores into this type of self-organized polymeric system enables the modulation of the amount of light emitted in the form of fluorescence upon deformation, giving rise to LSCE-based optical force sensors [19].…”

Section: Introductionmentioning

confidence: 99%

Structural Features Guiding the Design of Liquid-Crystalline Elastomeric Fluorescent Force Sensors

García-Amorós

Velasco

2020

ASI

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Liquid single crystal elastomers (LSCEs) containing carbazole fluorogenic components alter their luminescence when they are stretched along the director direction. The differential luminescent behavior arises from the distinct interaction between the carbazole fluorophores and their local environment before and after the application of the mechanical input. Indeed, the uniaxial deformation of the material, along its anisotropic direction, forces a closer mesogen–fluorophore interaction, which leads to the quenching of the carbazole luminescence. Importantly, this intermolecular interaction is intimately related to the intrinsic order present in the LSCE. As a result, the amount of light emitted by the material in the form of fluorescence diminishes upon deformation. Thus, the application of mechanical stimuli to liquid-crystalline elastomers furnishes to two interconvertible states for the system with distinct optical properties (with either different emission color or fluorescence intensity). The initial state of the material is completely restored once the applied force is removed. In this way, this kind of macromolecular system can transduce mechanical events into detectable and processable optical signals, thus, having great potential as optical force sensors. In this context, the realization of the distinct structural factors that govern the interactions established between the mesogenic and fluorogenic units at the supramolecular level upon deformation is essential for the development of efficient LSCE-based force sensors. In fact, not only the density of carbazole units and their connection to the main polymer backbone, but also the presence of long range molecular order in the system and the type of mesophase exhibited by the LSCE are key factors for the conception of efficient force sensors based on these self-organized polymer networks. In this review, we present a comprehensive and systematic description of the different features that control the mechanoluminescent behavior of fluorescent liquid-crystalline elastomers and will guide the future design of LSCE-based force sensors with improved performances.

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Effective structural modification of traditional fluorophores to obtain organic mechanofluorochromic molecules

Abstract: The review focuses on the influence of some important factors on the generation of new and/or high contrast mechanofluorochromic-active organic compounds by the structural modifications of traditional fluorophores.

Cited by 132 publications

References 102 publications

Circularly Polarized Luminescence in Nanoassemblies: Generation, Amplification, and Application

Circularly Polarized Luminescence in Nanoassemblies: Generation, Amplification, and Application

Aggregation‐Induced Emission‐Active 1,4‐Dihydropyridine‐Based Dual‐Phase Fluorescent Sensor with Multiple Functions

Structural Features Guiding the Design of Liquid-Crystalline Elastomeric Fluorescent Force Sensors

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