Solid-state acidochromic properties of barbituric acid-based 1,4-dihydropyridine derivatives with multiple coloured emissions switching

Wang, Mengzhu; Qian, Lebin; Guo, Yang; Wu, Huayue; Liu, Miaochang; Gao, Wenxia; Li, Guoxing; Ding, Jinchang; Huang, Xiaobo

doi:10.1016/j.dyepig.2018.08.018

Cited by 20 publications

(7 citation statements)

References 67 publications

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“…Furthermore, some 1,4‐dihydropyridine derivatives reportedly exhibit solid‐state fluorescence color changes upon external stimuli such as exposure to pressure, acidic vapor, organic vapor, and heat. Namely, they exhibit mechanochromic (MC), acidochromic, vapochromic, and thermochromic properties, respectively . However, 1,4‐dihydropyridine derivatives that exhibit stimulus‐responsive activities in both the solid and solution state are rarely reported.…”

Section: Introductionmentioning

confidence: 70%

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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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Section: Introductionmentioning

confidence: 70%

“…Namely,t hey exhibit mechanochromic (MC), acidochromic, vapochromic, and thermochromic properties, respectively. [22][23][24][25][26][27] However,1 ,4dihydropyridine derivatives that exhibit stimulus-responsivea ctivitiesi nb oth the solid and solution state are rarely reported.…”

Section: Introductionmentioning

confidence: 99%

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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“…According to the previous studies on the stimuli of the acid− base system, most of the mechanisms were attributed to the protonation and deprotonation in the process. 11,37,40 In order to further study the changes in the process of acid−base fumigation, the ligand HL was synthesized, and its crystal data are shown in Table S1 Interestingly, when ZnL 2 −HCl was fumigated with ethanol, the red film, which is attributed to HL on the surface, gradually faded (Figure S9a). Furthermore, it could be washed away by immersing in ethanol, and the crystal returned to a yellow color as well as the initial emission position, indicating a return to the initial state (Figure S9b).…”

Section: ■ Results and Discussionmentioning

confidence: 97%

“…Solid-state luminescent materials featuring stimuli-responses have attracted great interest due to their wide applications in the fields of sensors, optoelectronic devices, biomedical imaging, and security systems. − Specifically, the stimuli-responsive materials with reversible luminescent color changes under external stimuli such as heating, vapors, or force have aroused great attention. ,− In particular, the high contrast luminous color or intensity is very important during the reversible process, which is convenient to be observed by the naked eye in practical applications. − The structures of organic compounds are easy to be modified. The molecular interaction can be adjusted by changing the functional groups and the molecular aggregation mode to achieve the purpose of changing the luminescence properties.…”

Section: Introductionmentioning

confidence: 99%

Multistimuli Responsive Solid-State Emission of a Zinc(II) Complex with Multicolour Switching

Zheng

Yang

et al. 2021

Inorg. Chem.

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The development of smart luminescent materials, especially those stimulus-responsive fluorescent materials that can switch between different colors repeatedly under external stimulation based on a single molecule, is of great significance but a challenge. In this work, a novel zinc(II)−Schiff base complex (ZnL 2 ) was obtained and characterized. Upon exposure to the HCl and NH 3 vapors, it displayed remarkable tricolor acidochromic behavior with high contrast and rapid response under the ambient light as well as UV light (365 nm). The XPS analyses of ZnL 2 crystals before and after HCl/NH 3 fuming show that the acidochromism originates principally from the adsorption of vapor and the gas−solid reaction equilibrium on the crystal surface. The reddish-brown color of the HCl-fumigated ZnL 2 crystals could be attributed to the generation of HL at the surface of ZnL 2 , and red-shifted emission could be ascribed to the self-absorption effect. The single crystal X-ray diffraction data indicate that these processes cause slight changes in the molecular conformation and crystal packing. ZnL 2 shows reversible mechanochromic luminescence behavior between yellow and orange emission during the grinding−fuming/heating cycles due to the modulation between amorphous and crystalline states. Moreover, ZnL 2 was successfully made into test paper for the rapid detection of HCl/NH 3 vapors and mechanical stimuli.

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“…In 2006, Peng et al synthesized fluorescent polymers with incorporated 1 H -pyridine-4-ylidene structural fragments. A detailed investigation of 4 H -pyran-4-ylidene-fragment-containing compounds with primary and secondary amines and well-defined evidence of 1 H -pyridine-4-ylidene derivative chemical structures by X-ray analysis were reported several years later. − Recently, several 2,6-bis-styryl-substituted-1 H -pyridine-4-ylidene derivatives were successfully synthesized and reported as materials with aggregation-induced emission enhancement (AIEE) and multicolor switching properties. ,− Merocyanines are known for their prominent glass-forming and solid-state emission properties . While many J-aggregates usually exhibit strong fluorescence, the examples of a merocyanine H-aggregate exhibiting well-resolved emission with a longer fluorescence lifetime relative to that of the monomer was reported recently, proving the possibility of the usage of such kind of derivatives as materials exhibiting AIEE .…”

Section: Introductionmentioning

confidence: 99%

HAPPY Dyes as Light Amplification Media in Thin Films

et al. 2021

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A series of 1H amorphous tri-phenyl pyridine (HAPPY) dyes have been synthesized from luminescent triphenyl-groupcontaining 2-methyl-6-styryl-substituted-4H-pyran-4-ylidene derivatives in reactions with benzylamine and investigated for suitability as solution-processable light-emitting medium components in thin films for amplified spontaneous emission (ASE). Conversion of a 4H-pyrane ring into a 1H-pyridine fragment enables aggregation-induced emission enhancement (AIEE) behavior in the target products and slightly increases thermal stability, glass transition temperatures, and ASE efficiency with PLQY up to 15% and ASE thresholds as low as 46 μJ/ cm 2 in neat spin-cast films, although thermal and photophysical properties are mostly dominated by the incorporated electron acceptors. Continued lasing parameter efficiency parameter improvement experiments revealed that no further optimization of HAPPY dyes by doping in polymer matrixes is required as the amplified spontaneous emission thresholds were lowest in pure neat films due to the AIEE phenomenon.

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Solid-state acidochromic properties of barbituric acid-based 1,4-dihydropyridine derivatives with multiple coloured emissions switching

Cited by 20 publications

References 67 publications

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

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

Multistimuli Responsive Solid-State Emission of a Zinc(II) Complex with Multicolour Switching

HAPPY Dyes as Light Amplification Media in Thin Films

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