A perpendicular phenyl-induced exceedingly efficient solid-state excited state intramolecular proton transfer fluorophore based on 2-(2-hydroxyphenyl)benzothiazole

Wang, Qin; Xu, Longfei; Niu, Yahui; Wang, Yuxiu; Yuan, Mao-Sen; Zhang, Yanrong

doi:10.1016/j.dyepig.2016.11.055

Cited by 18 publications

(6 citation statements)

References 45 publications

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“…Another widely used backbone that is used to construct ESIPT‐based AIEgens is 2‐(2′‐hydroxyphenyl)benzothiazole (HBT, Scheme 2I with X = S), which is a typical ESIPT fluorophore bearing an intramolecular hydrogen bond O─H···N and show AIE properties by virtue of RIM mechanism. [ 31, 36, 42, 45, 46, 56, 59, 63, 73, 76, 81, 100, 103, 108, 120–123, 126, 131 , 180–194 ] The emissions of HBT derivatives are easily tunable and extended to the red region, making them advantageous to be applied in bioimaging. [ 103, 126, 192, 193, 195 ] In addition, a few of ESIPT‐based AIEgens based on 2‐(2′‐hydroxyphenyl)benzimidazole (HBI, Scheme 2I with X = NH), [ 196 ] and 2‐(2′‐aminophenyl)benzothiazole (ABT, Scheme 2J) [ 52, 63, 90, 101, 114, 197 ] have been reported.…”

Section: Backbones Of Esipt‐aie Luminogensmentioning

confidence: 99%

ESIPT‐based AIE luminogens: Design strategies, applications, and mechanisms

2022

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In this review, we present a systematic and comprehensive summary of the recent development and applications of excited-state intramolecular proton transfer-based (ESIPT-based) aggregation-induced emission luminogens (AIEgens), a type of promising materials that inherit the advantages of ESIPT and AIE, such as large Stokes shift, excellent photostability, and low self-quenching. We first summarize the backbones that have been used to construct the ESIPT-based AIEgens and classify the constructed ones based on the relation between ESIPT and AIE unit. According to the sensing mechanisms and design strategies, we have reviewed the applications of ESIPT-based AIEgens in bioimaging, drug delivery systems, organic lightemitting diodes, photo-patterning, liquid crystal, and the detection of metal cations, anions, small molecules, biothiols, biological enzymes, latent fingerprinting, and so on. We have also reviewed the recent advances in the development of new theoretical methods for investigating molecular photochemistry in crystals and their applications in ESIPT-based AIEgens. We discussed the remaining challenges in this field and the issues that need to be addressed. We anticipate that this review can provide a comprehensive picture of the current condition of research in this field, and promote researchers to make more efforts to develop novel ESIPT-based AIEgens with new applications.

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Section: Backbones Of Esipt‐aie Luminogensmentioning

confidence: 99%

ESIPT‐based AIE luminogens: Design strategies, applications, and mechanisms

2022

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“…The molecular spatialc onfigurations and packing modes of the three HBT derivativesw ere examined to determinet he photophysical properties of their crystalline states. [28] Thed istances of H···N in HBT-s-NO 2 ,H BT-t-NO 2 ,a nd HBT-d-NO 2 were found to be 1.939, 1.873, and 1.836 ,r espectively ( Figure 7A-C), whereas the dihedral angles between the phenol andb enzothiazole rings are 8.918,6 .698,a nd 2.018,r espectively (Figures 7D-F). These data indicate that the OÀH···N hydrogenbond in HBT-d-NO 2 is the strongest,w hichf acilitatesp roton transfer from Ot oNthrough OÀH···N bonding, and accounts for the largest F f .…”

Section: Resultsmentioning

confidence: 98%

Nitrostyrene‐Modified 2‐(2‐Hydroxyphenyl)benzothiazole: Enol‐Emission Solvatochromism by ESICT‐ESIPT and Aggregation‐Induced Emission Enhancement

Niu

Wang

Shao

et al. 2018

Chemistry A European J

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Excited-state intramolecular charge transfer (ESICT) and excited-state intramolecular proton transfer (ESIPT) are two competitive reactions that occur in the excited states of organic dyes that contain intramolecular hydrogen-bonds and electron acceptors and donors. Determining the mechanisms of these processes is key to understanding their multiple emission features, as the manner in which these processes interact can be modulated by modifying the dye structure. In addition, donor-π-acceptor (D-π-A) molecules often suffer from aggregation-induced quenching. Herein, we report the synthesis of three nitrophenyl-modified 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives, HBT-s-NO , HBT-d-NO , and HBT-t-NO , which have C-C, C=C, and C≡C bonds between their HBT and nitrophenyl moieties, respectively. Compared with the enol emissions from HBT-s-NO and HBT-t-NO , that from HBT-d-NO exhibits outstanding solvatochromism owing to consecutive ESICT-ESIPT. In addition, X-ray diffraction reveals that despite the highly planar and polar nature of HBT-d-NO , which is strongly H-aggregated, it exhibits highly efficient fluorescence. Hence, this study provides new insight into the design of ESICT/ESIPT-coupled systems and for engendering planar dipolar molecules with excellent emission properties in the solid state.

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“…It is noteworthy that the fluorescence spectral characteristic of DHPOD fibers with double fluorescence emission has also appeared in many excited-state intramolecular proton transfer (ESIPT) molecules whose molecular structures contain intramolecular hydrogen bonds between heterocycles and phenolic hydroxyl groups. [21][22][23][24][25][26][27][28][29][30][31][32] Thus, as similar as ESIPT molecules documented before, DHPOD macromolecules may undergo an ESIPT reaction as well. As depicted in Figure 4b, upon ultraviolet light excitation, the enol tautomer (S 0 ) transits to its first excited state (S 1 ).…”

Section: Uv Resistance Mechanism Of Dhpod Fibersmentioning

confidence: 90%

Ultraviolet resistance modification of poly(1,3,4‐oxadiazole) fibers by dihydroxyterephthalic acid

Feng

Xie

et al. 2022

J of Applied Polymer Sci

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Dihydroxyl poly(1,3,4‐oxadiazole) (DHPOD) polymers are synthesized by copolymerization of 2,5‐dihydroxyterephthalic acid (2,5‐DHTA) and terephthalic acid with hydrazine sulfate in oleum, and then DHPOD fibers are prepared by wet‐spinning. The effects of UV irradiation on POD fibers' mechanical properties and surface morphology with and without hydroxyl groups were investigated. As proved by tensile testing and scanning electron microscope measurement, the UV resistance of DHPOD fibers is improved compared to that of p‐POD fibers. Besides, the heat resistance of POD fibers is not damaged by the introduction of phenolic hydroxyl groups. The UV and fluorescence spectra are used to analyze the UV resistance mechanism of the POD containing phenolic hydroxyl groups. Results show that the UV resistance mechanism of DHPOD is related to the proton transfer reaction between the 1,3,4‐oxadiazole ring and ortho phenolic hydroxyl group.

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A perpendicular phenyl-induced exceedingly efficient solid-state excited state intramolecular proton transfer fluorophore based on 2-(2-hydroxyphenyl)benzothiazole

Cited by 18 publications

References 45 publications

ESIPT‐based AIE luminogens: Design strategies, applications, and mechanisms

ESIPT‐based AIE luminogens: Design strategies, applications, and mechanisms

Nitrostyrene‐Modified 2‐(2‐Hydroxyphenyl)benzothiazole: Enol‐Emission Solvatochromism by ESICT‐ESIPT and Aggregation‐Induced Emission Enhancement

Ultraviolet resistance modification of poly(1,3,4‐oxadiazole) fibers by dihydroxyterephthalic acid

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