The influence of different N-substituted groups on the mechanochromic properties of 1,4-dihydropyridine derivatives with simple structures

Zhou, Yibin; Qian, Lebin; Liu, Miaochang; Wu, Ge; Gao, Wenxia; Ding, Jinchang; Huang, Xiaobo; Wu, Huayue

doi:10.1039/c7ra09515e

Cited by 13 publications

(5 citation statements)

References 41 publications

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“…Scheme shows the chemical structure and synthetic route of NDHP. The reaction of the starting compound 2,6‐dimethyl‐4‐pyrone ( 1 ) with 5,5‐dimethylcyclohexane‐1,3‐dione in dimethyl sulfoxide (DMSO) gave 4 H ‐pyran derivative 2 , which further reacted with phenethylamine in acetonitrile to afford 1,4‐dihydropyridine derivative 3 . The target compound NDHP was facilely prepared with a yield of 67.4 % by the Knoevenagel reaction of compound 3 and 2‐naphthaldehyde in the presence of K 2 CO 3 .…”

Section: Resultsmentioning

confidence: 70%

“…Synthesis and characterization of NDHP Scheme 1s hows the chemical structure and synthetic route of NDHP.T he reaction of the startingc ompound 2,6-dimethyl-4pyrone (1)w ith 5,5-dimethylcyclohexane-1,3-dione in dimethyl sulfoxide (DMSO) gave 4 H-pyran derivative 2, [28] which further reactedw ith phenethylamine in acetonitrile to afford 1,4-dihydropyridine derivative 3. [28] The target compound NDHP was facilely prepared with ay ield of 67.4 %b yt he Knoevenagel reaction of compound 3 and 2-naphthaldehyde in the presence of K 2 CO 3 .T he chemical structure of NDHP was fully characterized by mass spectroscopies, 1 HNMR and 13 CNMR spectroscopy,e lemental analysis, and single-crystal structure analysis. NDHP has good solubility in CH 2 Cl 2 ,C HCl 3 ,t etrahydrofuran (THF), CH 3 CN, ethyl acetate (EA), methanol, ande thanol, but low solubility in water.…”

Section: Resultsmentioning

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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Section: Resultsmentioning

confidence: 70%

Section: Resultsmentioning

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

Self Cite

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“…The shape of the low-energy emission band becomes narrow, while the emission maximum is red-shifted from 545 to 557 nm for compound 1 and from 569 to 579 nm for compound 2, which are also typical features of the mechanochrmic excited states. Therefore, the MCL properties of the compounds should be attributed to a crystal-to-crystal transformation [15]. Considering that the changes in fluorescence spectra and colors of the MCL-active compounds were often accompanied by significant changes in fluorescence lifetimes, time-resolved solid-state emission was investigated.…”

Section: X-ray Diffraction and Pl Spectra For Analyzing Mechanochromi...mentioning

confidence: 99%

Mechanochromic luminescent derivatives based on xanthenone and thioxanthenone for the fabrication of OLED devices as emitter layer

Nasiri

Janušas

2023

Smart Materials for Opto-Electronic Applications

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New compounds consisting of xanthenone and thioxanthenone derivatives are synthesized and the photophysical properties of the compounds are discussed in detail. The difference between singlet and triplet energies was obtained at 0.09 and 0.37 eV (at low temperature). Furthermore, the logarithm of the laser power versus the logarithm of the PL intensity showed a slope of less than 1, and the compounds exhibit thermally activated delayed fluorescence (TADF). In addition, the photoluminescence quantum yield of the spin-coated films was gained 51.83 and 41.22%, respectively. The powder X-ray diffraction of the grinded (under the force) compounds and also the PL spectrum of the compounds were shifted and the compounds were mechanochromic when the color of the compounds was changed. The ionization potential of the compounds showed (5.49 and 5.62 eV) that the compounds were well suited for using in the fabrication of OLED devices as an emitter layer. The performance of the OLEDs was investigated and the maximum brightness and external quantum efficiency were found to be 44573 cdm-2 and 12.61%, respectively.

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“…57 In the literature, many reported organic fluorophores exhibited outstanding fluorescence behaviour due to conformational rigidity. [58][59][60] The fluorescence quantum yields of form 1 and form 1 + 2 of compound A were determined to be 1.8% and 0.9%, respectively, by using the integrating sphere method.…”

Section: Structural Analysismentioning

confidence: 99%

Solid-state fluorescence of a quasi-isostructural polymorphic biphenyl based Michael addition product

et al. 2022

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The influence of different N-substituted groups on the mechanochromic properties of 1,4-dihydropyridine derivatives with simple structures

Abstract: Four twisted 1,4-dihydropyridine derivatives with simple structure were synthesized. N-Substituted groups were found to play a decisive role in determining whether or not these compounds have mechanochromic activities.

Cited by 13 publications

References 41 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

Mechanochromic luminescent derivatives based on xanthenone and thioxanthenone for the fabrication of OLED devices as emitter layer

Solid-state fluorescence of a quasi-isostructural polymorphic biphenyl based Michael addition product

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