Pyrene meets 2-(2-hydroxyphenyl)benzothiazole: Creation of highly efficient solid-state monomeric emitter for organic light-emitting diode

Niu, Yahui; Wang, Rong; Pu, Liang; Zhang, Yanrong

doi:10.1016/j.dyepig.2019.107594

Cited by 19 publications

(11 citation statements)

References 36 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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“…自唐本忠课题组 [97] 首次研究发现 2-(2'-羟基苯基)苯并噻唑由于 RIM 和 ESIPT 机制的协同作用而具有 AIE 特性以来, 苯并噻唑常作为基本单元来开发 ESIPT 类 AIEgen [98] . 张艳荣课题组 [99] 通过将 ESIPT 活性染料化也成功开发了两种具有 AIE 和 ESIPT 特性的新型荧光分子 59 [100] 和 60 [101] [102] .…”

Section: Esipt 类 Aiegenunclassified

Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules

Chen¹,

Jia-dong²,

Li³

et al. 2022

Chinese Journal of Organic Chemistry

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“…Hence, MPP-s and MPP-d possessg ood coplanar geometry,w hich is highlyc onducive to cofacial intermolecular p-p stacking. [23] As shown in the crystal packing diagrams of MPP-s (Figure 10 A), two adjacent molecules adopt ap arallel alignment with an interplanar distance of 3.630 (relatively weaker intermolecular p-p interaction) , [24] and al arge overlap between two planes can be observedf rom the top view. Therefore, these two neighboring molecules form ar elatively unstabled imer, [25] whichw as connected with the surrounding molecules through three kinds of CÀH···p interactions.I nM PPd, along the b axis, two adjacent molecules adopt an antiparallel packing with 3.417 distance (relativelys tronger intermolecular p-p interaction), in which the electron-rich MP ring is located on the electron-deficient BT moiety ( Figure 10B1).…”

Section: Full Papermentioning

confidence: 99%

“…After cooling down to room temperature, the mixture was subsequently diluted with DCM, washed with water and dried over Na 2 SO 4 .A fter solvent removal under reduced pressure, the residue was purified by silica gel column chromatography (DCM) to afford the target product (129.6 mg, yield:5 0%)a sy ellow solid (129.8 mg). HRMS (ESI) m/z calcd for C 23 46, 154.35, 153.77, 153.61, 151.01, 149.50, 141.25, 135.92, 134.88, 134.08, 126.81, 125.93, 125.60, 123.73, 122.61, 121.89, 121.49, 117.00, 113.81, 111.31, 105.18, 56.41, 56.37 ppm.…”

Section: Synthesis Of Mpp-d-cnmentioning

confidence: 99%

Effect of Conjugation Mode on Intramolecular Charge Transfer in Fabricating Acid‐Responsive Fluorophores

Wang

Zhang

2019

Chemistry An Asian Journal

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Solid-state acid-responsivem aterials are promising for the tunability of their intrinsic properties. However, the relationship between molecular structure and emission shift as ar esponse to acid stimuli has not been systematically studied. Herein,w ereport the effect of protonation and subsequent intramolecular hydrogen bondingo nt he photophysical properties of compounds (MPP-s, MPP-d, and MPPd-CN) with different conjugation modes between the electron-donatingd imethoxyl phenyl and the electron-withdrawing benzothiazole ring. The resultse stablished that the stronger the intramolecular charget ransfer feature of the compound, the smaller is the emission shift after acid stimuli. Our studies alsoi ndicated that the conjugation modes ignificantlya ffected the solid-state packing mode:M PP-s and MPP-d tended to form dimers, while MPP-d-CNe xhibited the strongesta ggregation-induced emission enhancement (AIEE). The exploration of structure-property relationship would provide experimental andt heoretical guidance in designing acid-responsive molecular switches and developing high-performance AIEE-active luminogens.Scheme1.A) Some representative past studies on the formation of the intramolecular H-bonding;B)The molecular structures studied in this paper.

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Pyrene meets 2-(2-hydroxyphenyl)benzothiazole: Creation of highly efficient solid-state monomeric emitter for organic light-emitting diode

Cited by 19 publications

References 36 publications

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

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

Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules

Effect of Conjugation Mode on Intramolecular Charge Transfer in Fabricating Acid‐Responsive Fluorophores

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