Aminated and amidated structures introduced by ethylenediamine pretreatment endow lignin with bright fluorescence

Shi, Tao; Xu, Li; Wang, Yanan; Liu, Shichang; Liu, Zhihua; Zhao, Guangjiu; Li, Bingzhi; Yuan, Ying‐Jin

doi:10.1039/d2gc02120j

Cited by 20 publications

(4 citation statements)

References 75 publications

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“…The energy gap between the π-orbitals of O, N, and S and the n-orbitals of C decreased sequentially, and the energy required for electrons to jump from the π-orbitals to the n-orbitals of CO, CN, and CS decreases, which improved the fluorescence properties of LNP significantly . The red-shift occurred because the unpaired p-electrons on the electron-donating nitrogen-containing group (−NH 2 ) of EDA interact with the benzene ring and/or oxygen atom to form a conjugated structure . The resulting electron cloud overlap or electron delocalization can be achieved by reducing the energy gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) (as shown in Figure S8) to red-shift the emission wavelength and improve fluorescence properties.…”

Section: Resultsmentioning

confidence: 99%

“…46 The red-shift occurred because the unpaired p-electrons on the electron-donating nitrogencontaining group (−NH 2 ) of EDA interact with the benzene ring and/or oxygen atom to form a conjugated structure. 47 The resulting electron cloud overlap or electron delocalization can be achieved by reducing the energy gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) (as shown in Figure S8) to red-shift the emission wavelength and improve fluorescence properties.…”

Section: Fluorescent Properties Of Levmentioning

confidence: 99%

See 1 more Smart Citation

Preparation of Vitamin-g-Lignin Nanohybrids with Excellent Biological Activity and Fluorescence Performance

Yang,

Zhang,

Zhang

et al. 2024

Biomacromolecules

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Section: Resultsmentioning

confidence: 99%

Section: Fluorescent Properties Of Levmentioning

confidence: 99%

Preparation of Vitamin-g-Lignin Nanohybrids with Excellent Biological Activity and Fluorescence Performance

Yang,

Zhang,

Zhang

et al. 2024

Biomacromolecules

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“…According to the frontier molecular orbital theory, the HOMO–LUMO energy difference drives the adsorption process in MOFs. The HOMO reflects the electron-losing ability, the LUMO reflects the electron-gaining ability, and the distance between them affects the electron migration between orbitals, which determines the quality of chemisorption. , Figure a,b illustrates the HOMO and LUMO of Zn-MOFs before and after iodine adsorption. Zn-MOF-2 had a smaller energy gap ( E g ) compared to Zn-MOF-1, indicating that Zn-MOF-2 may produce better chemisorption.…”

Section: Analysis and Discussionmentioning

confidence: 99%

Analysis of Radioactive Iodine Trapping Mechanism by Zinc-Based Metal–Organic Frameworks with Various N-Containing Carboxylate Ligands

et al. 2023

ACS Appl. Mater. Interfaces

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This study aimed to develop effective adsorbents for capturing radioactive iodine in nuclear power waste gas. Two zinc metal−organic frameworks (Zn-MOFs) were synthesized and found to have favorable properties such as a large surface area, thermal stability, surface rich in π-electron-containing nitrogen, and redox potential. Adsorption experiments revealed maximum capacities of 1.25 and 1.96 g g −1 for the MOFs at 75 °C, with the pseudo-second-order kinetic model fitting the data well. The Langmuir equation provided a better fit in cyclohexane, with maximum adsorption amounts of 249 and 358 mg g −1 for Zn-MOF-1 and Zn-MOF-2, respectively. The MOFs were also stable during six cycles of adsorption and desorption. Furthermore, electron transfer occurred due to the synergistic adsorption of Zn, N, and O atoms, resulting in the conversion of some iodine to polyiodide. Zn-MOF-2 exhibited better chemisorption than Zn-MOF-1 due to a smaller highest occupied molecular orbital (HOMO)−lowest unoccupied molecular orbital (LUMO) gap. Notably, it was discovered that N-containing radicals had stronger interactions with iodine compared to radicals without N. These findings provide valuable insights into MOF synthesis and environmental protection.

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“…This also proves that the introduction of amine groups is a key factor to improve the photoluminescence performance. The grafting of amide groups and luminescent clusters onto the lignin benzene ring brings the atoms closer to each other, thus facilitating intramolecular charge transfer, which is enhanced by bonding and/or spatial interactions [57][58][59][60][61]. Luminescent clusters promote luminescence through the formation of spatial interactions.…”

Section: Fluorescence Propertiesmentioning

confidence: 99%

One-Step to Prepare Lignin Based Fluorescent Nanoparticles with Excellent Radical Scavenging Activity

Zhang,

Abushammala,

Puglia

et al. 2024

JRM

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Fluorescent nanomaterials have attracted much attention, due to their unique luminescent properties and promising applications in biomedical areas. In this study, lignin based fluorescent nanoparticles (LFNP) with high yield (up to 32.4%) were prepared from lignin nanoparticles (LNP) by one-pot hydrothermal method with ethylenediamine (EDA) and citric acid. Morphology and chemical structure of LFNP were investigated by SEM, FT-IR, and zeta potential, and it was found that the structure of LFNP changed with the increase of citric acid addition. LFNP showed the highest fluorescence intensity under UV excitation at wavelengths of 375-385 nm, with emission wavelengths between 454-465 nm, and exhibited strong photoluminescence behavior. Meanwhile, with the increase of citric acid content, the energy gap (ΔE) gradually decreased from 3.87 to 3.14 eV, which corresponds to the gradual enhancement of fluorescence performance. LFNP also exhibited excellent antioxidant activity, with DPPH free radical scavenging rate increased from 80.8% for LNP up to 96.7% for LFNP, confirming the great potential of these materials for application in biomedicine and cosmetic health care.

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Aminated and amidated structures introduced by ethylenediamine pretreatment endow lignin with bright fluorescence

Abstract: As a natural photoluminescence (PL) polymer, lignin has enormous potential in the fabrication of sustainable and environmentally friendly luminescent materials for various applications such as bio-imaging and chemical sensing. However,...

Cited by 20 publications

References 75 publications

Preparation of Vitamin-g-Lignin Nanohybrids with Excellent Biological Activity and Fluorescence Performance

Preparation of Vitamin-g-Lignin Nanohybrids with Excellent Biological Activity and Fluorescence Performance

Analysis of Radioactive Iodine Trapping Mechanism by Zinc-Based Metal–Organic Frameworks with Various N-Containing Carboxylate Ligands

One-Step to Prepare Lignin Based Fluorescent Nanoparticles with Excellent Radical Scavenging Activity

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