Piezochromism, acidochromism, solvent-induced emission changes and cell imaging of D-π-A 1,4-dihydropyridine derivatives with aggregation-induced emission properties

Lei, Yunxiang; Yang, Dongliang; Hua, Huaijie; Dai, Chunhui; Wang, Lianhui; Liu, Miaochang; Huang, Xiaobo; Guo, Yang; Cheng, Yixiang; Wu, Huayue

doi:10.1016/j.dyepig.2016.06.008

Cited by 37 publications

(23 citation statements)

References 44 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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“…On the other hand, the CO linker increases the conjugation of the molecular,t hus resulting in al onger wavelength. [24,25] Hence, we believe our work can considerably contribute to the designing of new AIE compounds, to the under-standing of the AIE phenomenona nd mechanism, and to expanding the application fields of AIE-based materials.…”

Section: Introductionmentioning

confidence: 90%

“…Considering that CO has ab etter conjugation than CN, CO-containing molecules tend to have al ong emission wavelength. [24] In this work, the donor and acceptor are linked through an alkyl chain containingP(pyridone derivative) or B( benzopyran derivative). Pl inker has ah ighly twisted molecular structure, which is favorable for the targetc ompound to have strong fluorescencei ntensity.…”

Section: Introductionmentioning

confidence: 99%

“…Pl inker has ah ighly twisted molecular structure, which is favorable for the targetc ompound to have strong fluorescencei ntensity. [24] On the other hand, the conjugation of Bl inker is relativelyh igh, which is advantageous for the material to have al ong emission wavelength. [25] Based on this strategy, we designed and synthesized eight D-p-A compounds.A mongt hem, four are Pd erivatives, and the others are Bd erivatives.…”

Section: Introductionmentioning

confidence: 99%

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The Synergistic Effect between Triphenylpyrrole Isomers as Donors, Linking Groups, and Acceptors on the Fluorescence Properties of D–π–A Compounds in the Solid State

Lei

Lai

Dong

et al. 2017

Chemistry A European J

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Eight donor-π-acceptor (D-π-A) compounds employing triphenylpyrrole isomers (TPP-1,2,5 and TPP-1,3,4) as donors, malononitrile (CN) and 1H-indene-1,3(2H)-dione (CO) as acceptors, pyridone (P) and benzopyran (B) as π-linking groups were synthesized. The compounds exhibited aggregation-induced emission and piezochromic properties. Compared with previously reported donors, triphenylpyrroles induced all the compounds to have more remarkable photophysical properties. The compounds containing TPP-1,2,5 and P moieties displayed stronger fluorescence intensities, shorter emission wavelengths, and more distinct piezochromic properties. However, the same phenomenon was observed in the TPP-1,3,4-containing system if B was as π-linker. Moreover, the CN acceptor endowed the compound to have a relatively strong fluorescent intensity, in which CO induced a relatively long emission wavelength. That is, the photophysical properties of D-π-A compounds can be controlled by adjusting the structure of donor, linker and acceptor.

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The Dual‐State Luminescent Mechanism of 2,3,4,5‐Tetraphenyl‐1H‐pyrrole

Lei

Liu

Dong

et al. 2018

Chemistry A European J

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2,3,4,5-Tetraphenyl-1H-pyrrole (TePP) was synthesized by a simple one-step reaction. The compound showed a balanced emission in both the solution and solid state with the absolute quantum yield of Φ =65.6 % and Φ =74.3 %, respectively. Temperature and viscosity variation measurements demonstrated that the phenyl group at the 1-position (N-position) of the pyrrole core can act as a rotor in pyrrole-based molecules, which can consume the excited energy and reduce the molecular emission in solution. TePP without the phenyl group at the 1-position can effectively enhance the emission in solution. Single-crystal analysis showed that the phenyl groups at the 2,5-positions of pyrrole extend the molecular conjugation and lock the conformation. The phenyl groups at the 3,4-positions with a twisted conformation prevent their molecules from close packing and are helpful for aggregated emission. A delicate balance between the twisting conformation and rigid conjugation takes advantage of both ACQ and AIE luminogens. The strategy can tune the AIE, ACQ, or solution and solid dual-state emission properties of pyrrole-based molecules by simply altering the position of phenyl groups, which provides a great opportunity to explore the luminescent mechanism in greater detail and to facilitate practical applications.

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Piezochromism, acidochromism, solvent-induced emission changes and cell imaging of D-π-A 1,4-dihydropyridine derivatives with aggregation-induced emission properties

Cited by 37 publications

References 44 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

The Synergistic Effect between Triphenylpyrrole Isomers as Donors, Linking Groups, and Acceptors on the Fluorescence Properties of D–π–A Compounds in the Solid State

The Dual‐State Luminescent Mechanism of 2,3,4,5‐Tetraphenyl‐1H‐pyrrole

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