Intramolecular charge-transfer emission from conjugated polymer nanoparticles: the terminal group effect on electronic and optical properties

Wu, Xiaofu; Li, Haibo; Xu, Yu X.; Tong, Hui; Wang, Lixiang

doi:10.1039/c5py00006h

Cited by 27 publications

(14 citation statements)

References 52 publications

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“…Many fluorescent-based moisture sensors are available in the literature based on different kinds of mechanisms such as fluorescence intensity change, − ratio fluorescence, − solvatochromism, and so on. − Besides organic probes, some luminescent nanomaterials-based sensors for water detection have also been developed . For example, covalent organic frameworks (COFs), carbon quantum dots, metal–organic frameworks (MOFs), copper nanoclusters, and other nanomaterials have been reported for sensing water in organic solvents.…”

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confidence: 99%

Excited State Intramolecular Proton Transfer Plus Aggregation-Induced Emission-Based Diketopyrrolopyrrole Luminogen: Photophysical Properties and Simultaneously Discriminative Detection of Trace Water in Three Organic Solvents

Wang

Tang

et al. 2019

Anal. Chem.

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Developing solid state near-IR (NIR) emitters and simultaneously discriminative detection of trace water in organic solvents has long been a significant challenge. In this work, a novel diketopyrrolopyrrole-based luminogen (DPP1) with excited state intramolecular proton transfer (ESIPT) and aggregation-induced emission (AIE) characteristics has been designed and synthesized. Its amorphous and crystal solids show red and NIR-emissive fluorescence at 625 and 675 nm, respectively. When DPP1 reacts with fluoride anion, the resulting system (DPP1·F) can discriminatively detect the water content in aprotic solvents with colorimetric and fluorescent dual modes. Distinct fluorescent responses of “turn-on”, “ratiometric turn-off”, and “ratiometric turn-on” and low limits of detection of 0.0064, 0.042, and 0. The water-induced sensitive and fast change in THF was applied to the determination of water in foodstuffs in practical solid state indicator paper strips.

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confidence: 99%

Excited State Intramolecular Proton Transfer Plus Aggregation-Induced Emission-Based Diketopyrrolopyrrole Luminogen: Photophysical Properties and Simultaneously Discriminative Detection of Trace Water in Three Organic Solvents

Wang

Tang

et al. 2019

Anal. Chem.

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“…The fluorescence emission spectra of Ta‐CMPs were obtained using their dispersion in various solvents (2 mg per 10 mL), including n ‐hexane (HEX), TOL, dichloromethane (DCM), THF, and DMF (Figure c). With an excitation wavelength of 365 nm, the maximum emissions of Ta‐CMP, Ta‐CMP‐N, and Ta‐CMP‐CN show red‐shift with the increase of solvent polarity, which proves the intramolecular charge transfer (ICT) effect of the polymers …”

Section: Resultsmentioning

confidence: 94%

Terminal Group Effect of Conjugated Microporous Polymers for Photocatalytic Water‐Splitting Hydrogen Evolution

Ding

Zhang

et al. 2019

Macro Chemistry & Physics

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hydrogen production from water splitting under visible light. [11] Since then, much effort has been concentrated on the relationship between molecular structure and the photo catalytic activity of CMPs. It is found that the structural factors, such as linkers geometry, conjugation length, and functional groups, play important roles in determining the wettability, charge transport and separation, light adsorption, and band gap of CMPs, thus affecting hydrogen production performance of CMPs-based photo catalysts. [9,[12][13][14][15] Among them, triazine-based CMPs are particularly interesting thanks to their abundant nitrogen content, high electron deficiency, and spatial coplanarity, thus they have been effectively applied in photocatalytic hydrogen evolution from water. [16,17] However, the influence of the terminal groups on hydrogen evolution performance of CMPs is still scarcely reported.In this work, three triazine-based CMPs (Ta-CMP, Ta-CMP-N, and Ta-CMP-CN) were synthesized by Suzuki-Miyaura cross-coupling reaction and end-capping strategy, among which Ta-CMP was synthesized without addition of any end-capping agent, while Ta-CMP-N and Ta-CMP-CN were end-capped with electron-donating dimethylaniline group and electronwithdrawing benzonitrile group, respectively. A study on the relationship between the terminal groups and the photocatalytic performances was also conducted. The result revealed that terminal groups have little effect on the morphology, specific surface area, and band gap, but have an impact on the electron and hole separation ability. Electron-withdrawing group can enhance the electron-hole separation efficiency, which is beneficial for the enhancement of the H 2 evolution performance of the photocatalyst, while the electron-donating group exhibits an opposite effect. Therefore, Ta-CMP-CN shows the best photocatalytic activity of 698 µmol g −1 h −1 under visible light, while hydrogen evolution rate (HER) of Ta-CMP-N is only 99 µmol g −1 h −1 . Results and Discussion Synthesis and CharacterizationAs shown in Scheme 1, Ta-CMP, Ta-CMP-N, and Ta-CMP-CN were synthesized by Suzuki-Miyaura cross-coupling reaction. Conjugated Microporous PolymersConjugated microporous polymers (CMPs) have attracted more and more attention as active materials for photocatalytic water-splitting hydrogen evolution, however, the correlation between terminal group and hydrogen evolution performance of CMPs is rarely studied. Herein, three triazine-based CMPs (Ta-CMPs) with the same polymer backbone and different terminal groups (Ta-CMP, Ta-CMP-N, and Ta-CMP-CN) are synthesized via Suzuki-Miyaura coupling reaction using different end-capping agents. Although the Ta-CMPs show similar porous structure and comparable band gaps, Ta-CMP-CN with electron-withdrawing terminal group exhibits the highest hydrogen evolution rate (HER) of 698 µmol g −1 h −1 under visible light, while Ta-CMP-N with electron-donating terminal group exhibits the lowest HER of 99 µmol g −1 h −1 . It is found that the addition of electron-withdrawing termi...

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“…[ 39 ] Zhang et al reported a series of new conjugated polymer fluorescent probes. [ 40 ] However, conjugated polymer synthesis methods are mainly about Suzuki coupling, [ 41,42 ] Yamamoto reaction, [ 43 ] Kumada reaction, [ 44 ] Heck reaction, [ 45 ] Sonogashira reaction. [ 46,47 ] These reactions are used in the process of non‐environmentally friendly solvents and heavy metal catalyst.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of 1,3‐butadiene‐containing hyperbranched conjugated polymers as a selective chemosensors for Fe³⁺ ions

Chen

Luo

et al. 2021

J of Applied Polymer Sci

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Hyperbranched conjugated polymers (P1, P2 and P3) containing different aryl groups appended with carboxylic ester groups were synthesized by metal‐free catalyzed polymerization via A2 + B3 type monomers. These as‐prepared polymers can be dissolved well in common organic solvents and have good thermal stability. These polymers were investigated as fluorescence chemosensor for the detection of biologically important metal ion Fe3+. The corresponding Stern‐Volmer constants (Ksv) of P1, P2 and P3 were 3.99 × 104 M−1, 5.15 × 104 M−1 and 3.99 × 104 M−1, respectively. The detection limits of 1.203 × 10−7 M for P1, 8.487 × 10−7 M for P2 and 7.158 × 10−6 M for P3 were achieved. In addition, the water‐soluble hyperbranched conjugated polymers were obtained by hydrolysis of neutral polymer P1, P2 and P3. The ability of water‐soluble polymers to detect Fe3+ ion in an aqueous solution was investigated in this work. The results demonstrated that the different aryl moieties in backbone of hyperbranched polymers mainly affected their energy band instead of their selective detection of Fe3+ ions. All the polymers were highly sensitive and selective toward Fe3+ ions in organic solvents and aqueous solution, indicating that these polymers could be used as fluorescence chemosensor for Fe3+ ions in real time.

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Intramolecular charge-transfer emission from conjugated polymer nanoparticles: the terminal group effect on electronic and optical properties

Abstract: Efficient tuning of electronic and optical properties of conjugated polymer nanoparticles by intramolecular charge transfer between the core and the terminal groups is demonstrated for the first time.

Cited by 27 publications

References 52 publications

Excited State Intramolecular Proton Transfer Plus Aggregation-Induced Emission-Based Diketopyrrolopyrrole Luminogen: Photophysical Properties and Simultaneously Discriminative Detection of Trace Water in Three Organic Solvents

Excited State Intramolecular Proton Transfer Plus Aggregation-Induced Emission-Based Diketopyrrolopyrrole Luminogen: Photophysical Properties and Simultaneously Discriminative Detection of Trace Water in Three Organic Solvents

Terminal Group Effect of Conjugated Microporous Polymers for Photocatalytic Water‐Splitting Hydrogen Evolution

Synthesis and characterization of 1,3‐butadiene‐containing hyperbranched conjugated polymers as a selective chemosensors for Fe³⁺ ions

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Intramolecular charge-transfer emission from conjugated polymer nanoparticles: the terminal group effect on electronic and optical properties

Abstract: Efficient tuning of electronic and optical properties of conjugated polymer nanoparticles by intramolecular charge transfer between the core and the terminal groups is demonstrated for the first time.

Cited by 27 publications

References 52 publications

Excited State Intramolecular Proton Transfer Plus Aggregation-Induced Emission-Based Diketopyrrolopyrrole Luminogen: Photophysical Properties and Simultaneously Discriminative Detection of Trace Water in Three Organic Solvents

Excited State Intramolecular Proton Transfer Plus Aggregation-Induced Emission-Based Diketopyrrolopyrrole Luminogen: Photophysical Properties and Simultaneously Discriminative Detection of Trace Water in Three Organic Solvents

Terminal Group Effect of Conjugated Microporous Polymers for Photocatalytic Water‐Splitting Hydrogen Evolution

Synthesis and characterization of 1,3‐butadiene‐containing hyperbranched conjugated polymers as a selective chemosensors for Fe3+ ions

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Synthesis and characterization of 1,3‐butadiene‐containing hyperbranched conjugated polymers as a selective chemosensors for Fe³⁺ ions