Phenothiazine substituted phenanthroimidazole derivatives: Synthesis, photophysical properties and efficient piezochromic luminescence

Zhan, Yong; Xu, Yongnan; Jin, Zhe; Ye, Wenjing; Yang, Pin

doi:10.1016/j.dyepig.2017.01.070

Cited by 31 publications

(13 citation statements)

References 56 publications

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“…Our group has attached the donor TPE directly to the PI core via the N and the C atom and has reported remarkable AIE and mechanofluorochromic properties. 34,39,59 61,62 In this work, the PTZ unit has been attached to the C atom of the PI unit which acts as an additional spacer unit while the attachment of donors of TPE and PTZ occurs through the C atom of the PI unit. The six derivatives encompass the change in position of the donors TPE (D) and PTZ (D′), use of two donors with contrasting donating abilities, use of an additional PTZ unit as a spacer, and change in the mode of attachment of the donors.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The mode of attachment of the donors and their position were also varied in these six derivatives, and its effect on their photophysical and electronic properties were studied. Our group has attached the donor TPE directly to the PI core via the N and the C atom and has reported remarkable AIE and mechanofluorochromic properties. ,, Qiu et al and Zhan et al have studied the photophysical and mechanochromic response by directly attaching the PTZ core to the C atom of the PI core. , In this work, the PTZ unit has been attached to the C atom of the PI unit which acts as an additional spacer unit while the attachment of donors of TPE and PTZ occurs through the C atom of the PI unit. The six derivatives encompass the change in position of the donors TPE (D) and PTZ (D′), use of two donors with contrasting donating abilities, use of an additional PTZ unit as a spacer, and change in the mode of attachment of the donors.…”

Section: Introductionmentioning

confidence: 99%

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Mechanochromism and Aggregation-Induced Emission in Phenanthroimidazole Derivatives: Role of Positional Change of Different Donors in a Multichromophoric Assembly

et al. 2021

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Organic materials possessing solid-state emission responsive to external stimuli have significance in a variety of material, biomedical, and optoelectronic applications. Organic molecules having different donor–acceptor architectures integrated with aggregation-induced emission (AIE) fluorophores have been utilized in development of mechanofluorochromic (MFC) materials. In this work, we have designed and synthesized phenanthroimidazole (PI) based derivatives TPE-PI-1, TPE-PI-2, TPE-PI-3, PTZ-PI-1, PTZ-PI-2, and PTZ-PI-3 where in donors tetraphenylethylene-TPE (D) and phenothiazine-PTZ (D′) of contrasting donor abilities are attached to the N and C atom positions of PI. The position and mode of attachment of the donors have been changed, and an additional PTZ spacer has been introduced which has a direct consequence on their photophysical and electronic properties. The PI derivatives manifest AIE, solvatochromic, and mechanochromic behavior. The single crystal X-ray analysis of TPE-PI-1 and PTZ-PI-2 reveals bent structures for the PTZ unit and a twisted conformation for TPE moieties. The density functional theory calculations were used to obtain optimized ground-state structures of the PI derivatives. The work shows a comprehensive comparison of the photophysical, electronic, AIE, and MFC properties of the PI derivatives as an effect of variations in the position of donor, donor–acceptor strength, and change in molecular conformation on use of spacer.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mechanochromism and Aggregation-Induced Emission in Phenanthroimidazole Derivatives: Role of Positional Change of Different Donors in a Multichromophoric Assembly

et al. 2021

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“…The MFC innovative materials have shown advanced application in different elds, such as mechanosensing, wearable devices, anti-counterfeiting, optical recording, security papers, data storage, and optoelectronics. [5][6][7][8][9][10][11][12][13] Regrettably, most classic emissive materials emit intense light in dilute solutions. However, this bright luminescence is oen attenuated or quenched at high concentrations, in a phenomenon known as aggregation-caused quenching (ACQ).…”

Section: Introductionmentioning

confidence: 99%

AIE and reversible mechanofluorochromism characteristics of new imidazole-based donor–π–acceptor dyes

et al. 2022

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“…Hybridized local and charge-transfer (HLCT) luminogens can convert dark triplet excitons to singlet excitons through reverse intersystem crossing (RISC) by reducing the single-triplet energy gap (Δ E ST ) and are potential candidates for harvesting efficient luminescence besides being phosphorescence emitters. , The HLCT materials consist of locally excited (LE) state and CT state characteristics. The LE component ensures relatively high fluorescence efficiency, and the CT component provides multistimuli-responsive fluorescence behavior, which may provide a new strategy to achieve high-efficient and high-contrast stimuli-responsive materials …”

Section: Introductionmentioning

confidence: 99%

Mechanoluminescence and Aggregation-Induced Emission in Bipolar Phenanthroimidazoles: Role of Positional Isomerization-Induced Switching Effect

Jayabharathi

Thanikachalam

Karunakaran

et al. 2022

Ind. Eng. Chem. Res.

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The newborn materials integrated with aggregation-induced emission (AIE) fluorophores, namely PyNPPI-CCz, PyCNPPI-CCz, PyNPPI-NCz, and PyCNPPI-NCz, show intense fluorescence in solution and films. They have good thermal stability (T g /T d , °C: 143/463-PyNPPI-CCz, 156/489-PyCNPPI-CCz, 199/498-PyNPPI-NCz, and 201/501-PyCNPPI-NCz) and exhibit reversible mechanochromism. In the aggregated phase, the restricted intramolecular rotation of phenyl rings reduced the nonradiative relaxation (k nr ) which enhanced the emission intensity with high photoluminescence quantum yield in films (PLQY f ) (0.43-PyNPPI-CCz, 0.68-PyCNPPI-CCz, 0.70-PyNPPI-NCz, and 0.86-PyCNPPI-NCz). The solid state of these materials shows a bluish green emission after grinding, and the color changes are reversible by heating. The reversible mechanofluorochromism can be confirmed by powder X-ray diffraction which implies the transformation between crystalline and amorphous states. Theoretical calculations of molecular couples of these materials suggest that the intermolecular interactions enhanced the dipole moment and the interchange of group positions in these molecules holds much larger dipole moment and contributed to their exceptional mechanoluminance performances.

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Phenothiazine substituted phenanthroimidazole derivatives: Synthesis, photophysical properties and efficient piezochromic luminescence

Cited by 31 publications

References 56 publications

Mechanochromism and Aggregation-Induced Emission in Phenanthroimidazole Derivatives: Role of Positional Change of Different Donors in a Multichromophoric Assembly

Mechanochromism and Aggregation-Induced Emission in Phenanthroimidazole Derivatives: Role of Positional Change of Different Donors in a Multichromophoric Assembly

AIE and reversible mechanofluorochromism characteristics of new imidazole-based donor–π–acceptor dyes

Mechanoluminescence and Aggregation-Induced Emission in Bipolar Phenanthroimidazoles: Role of Positional Isomerization-Induced Switching Effect

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