Synthesis, structure and mechanofluorochromic properties of phenothiazine-S-oxide and phenothiazine-S,S-dioxide derivatives

Zhang, Mingxing; Yang, Xiaofei; Tan, Fen; Zhang, Hongquan; Guo-ping, Zeng; Xu, Zhiqiang; Liu, Sheng Hua

doi:10.1016/j.saa.2023.122427

“…Under external mechanical stimulation, these weak non-covalent interactions were conducive to being destroyed, and the crystal structure was prone to collapse, resulting in the change of molecular configuration and the planarity of structural packing. 34 A red-shift MFC behavior was observed, and thus the crystalline-to-amorphous transition was achieved, and a reversible process could be restored by solvent fumigation.…”

Section: Resultsmentioning

confidence: 95%

A difluoroboron compound with latent fingerprint detection and inkless writing based on aggregation-induced emission enhancement and mechanofluorochromic behavior

Yang,

Tian,

Zhang

et al. 2024

New J. Chem.

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“…During the past few years, as a key versatile building block, the phenothiazine skeleton has been recognized for its ability to develop MFC materials, owing to its non-planar butterfly conformation and excellent photoelectric performance. 17–20…”

Section: Introductionmentioning

confidence: 99%

“…During the past few years, as a key versatile building block, the phenothiazine skeleton has been recognized for its ability to develop MFC materials, owing to its non-planar butterfly conformation and excellent photoelectric performance. [17][18][19][20] Herein, two new D-A type molecules based on the non-planar phenothiazine skeleton with different electron-withdrawing moieties have been constructed (Scheme 1). The introduction of subtle electron-withdrawing moieties is expected to lead to different mechanofluorochromism.…”

Section: Introductionmentioning

confidence: 99%

AIE-active non-planar phenothiazine-based derivatives with mechanical-induced emission enhancement characteristics

Zhu,

Zhang,

Zhang

et al. 2023

New J. Chem.

4

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Novel Dual‐Emission Emitters Featuring Phenothiazine‐S‐Oxide and Phenothiazine‐S,S‐Dioxide Motifs

Zhang,

Yang,

Tan

et al. 2024

Chemistry An Asian Journal

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In this study, we have successfully designed and synthesized two novel dual‐emission emitters featuring phenothiazine‐5‐oxide and phenothiazine‐5,5‐dioxide motifs, characterized by highly lopsided and asymmetric conformational states. Through rigorous spectral examinations and DFT calculations, the compounds exhibit distinctive ICT phenomena, coupled with efficient emission in solid states and AIEE characteristics under high water fractions in DMF/H2O mixtures. These non‐planar luminogens exhibit vibrant green and blue solid‐state luminescence, with fluorescence quantum yields of 24.1% and 15.21%, respectively. Additionally, they both emit green fluorescence in THF solution, with notable emission quantum yields 36.4% and 30.4%. Comprehensive theoretical investigations unveil well‐defined electron cloud density separation between the energies of HOMO/LUMO levels within the two luminogens. Notably, the targeted molecule harboring the phenothiazine‐S,S‐dioxide motif also demonstrates remarkable reversible mechanofluorochromic properties. Moreover, we testify their potential in applications such as solid‐state rewritable information storage and live‐cell imaging in solution states. Through theoretical calculations and comparative studies, we have explored the intrinsic relationship between molecular structure and performance, effectively screening and identifying new fluorescent molecules exhibiting outstanding luminescent attributes. These discoveries establish robust theoretical and technical foundation for the synthesis and application of efficient DSE‐based MFC materials, opening new avenues in the realm of advanced luminescent materials

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Synthesis, structure and mechanofluorochromic properties of phenothiazine-S-oxide and phenothiazine-S,S-dioxide derivatives

Cited by 8 publications

References 48 publications

A difluoroboron compound with latent fingerprint detection and inkless writing based on aggregation-induced emission enhancement and mechanofluorochromic behavior

A difluoroboron compound with latent fingerprint detection and inkless writing based on aggregation-induced emission enhancement and mechanofluorochromic behavior

AIE-active non-planar phenothiazine-based derivatives with mechanical-induced emission enhancement characteristics

Novel Dual‐Emission Emitters Featuring Phenothiazine‐S‐Oxide and Phenothiazine‐S,S‐Dioxide Motifs

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