Aggregation-induced emission: the origin of lignin fluorescence

Xue, Yuyuan; Qiu, Xueqing; Wu, Ying; Qian, Yong; Zhou, Mingsong; Deng, Yonghong; Li, Yuan

doi:10.1039/c6py00244g

Cited by 84 publications

(64 citation statements)

References 32 publications

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“…But even model lignin polymers fluorescence differs significantly depending on their composition 36 . Recently, it has been proposed that lignin fluorescence may originate from its aggregation due in particular to clustering of the carbonyl groups 37 . Since the origin of lignocellulose fluorescence is questionable, some model lignin dehydrogenative polymers (DHPs) made of 100% CA (DHP G) and 50% CA + 50% SA (DHP GS) were synthesized 38 .…”

Section: Discussionmentioning

confidence: 99%

Seeing biomass recalcitrance through fluorescence

Auxenfans

Terryn

Paës

2017

Sci Rep

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Lignocellulosic biomass is the only renewable carbon resource available in sufficient amount on Earth to go beyond the fossil-based carbon economy. Its transformation requires controlled breakdown of polymers into a set of molecules to make fuels, chemicals and materials. But biomass is a network of various inter-connected polymers which are very difficult to deconstruct optimally. In particular, saccharification potential of lignocellulosic biomass depends on several complex chemical and physical factors. For the first time, an easily measurable fluorescence properties of steam-exploded biomass samples from miscanthus, poplar and wheat straw was shown to be directly correlated to their saccharification potential. Fluorescence can thus be advantageously used as a predictive method of biomass saccharification. The loss in fluorescence occurring after the steam explosion pretreatment and increasing with pretreatment severity does not originate from the loss in lignin content, but rather from a decrease of the lignin β-aryl-ether linkage content. Fluorescence lifetime analysis demonstrates that monolignols making lignin become highly conjugated after steam explosion pretreatment. These results reveal that lignin chemical composition is a more important feature to consider than its content to understand and to predict biomass saccharification.

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Section: Discussionmentioning

confidence: 99%

Seeing biomass recalcitrance through fluorescence

Auxenfans

Terryn

Paës

2017

Sci Rep

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“…Phenylcoumarones as a pure compound in dioxane solution have quantum yields of 0.57-0.61 but the fluorescence intensity of lignin is likely to be much less than this and is strongly dependent on excitation wavelength (37). Lignin fluorescence may also be influenced by the physical structure of the polymer including clustering of carbonyl groups and restrictions on intramolecular rotation [40]. Studies on model compounds have focused on deep UV-excited fluorophores rather than visible wavelength fluorophores in lignin.…”

Section: Ligninmentioning

confidence: 99%

“…Both UV and visible emission spectra contain multiple log-normal components resulting from conjugated structures [35,36]. It is quite likely that lignin fluorescence results from resonant energy transfer among different structures [37,40]. When excited by blue laser light, lignin fluorescence shows evidence of weak whispering gallery resonance which may also result from resonant energy transfer processes ( Figure 4c) [45,46].…”

Section: Spectroscopymentioning

confidence: 99%

Autofluorescence in Plants

2020

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Plants contain abundant autofluorescent molecules that can be used for biochemical, physiological, or imaging studies. The two most studied molecules are chlorophyll (orange/red fluorescence) and lignin (blue/green fluorescence). Chlorophyll fluorescence is used to measure the physiological state of plants using handheld devices that can measure photosynthesis, linear electron flux, and CO2 assimilation by directly scanning leaves, or by using reconnaissance imaging from a drone, an aircraft or a satellite. Lignin fluorescence can be used in imaging studies of wood for phenotyping of genetic variants in order to evaluate reaction wood formation, assess chemical modification of wood, and study fundamental cell wall properties using Förster Resonant Energy Transfer (FRET) and other methods. Many other fluorescent molecules have been characterized both within the protoplast and as components of cell walls. Such molecules have fluorescence emissions across the visible spectrum and can potentially be differentiated by spectral imaging or by evaluating their response to change in pH (ferulates) or chemicals such as Naturstoff reagent (flavonoids). Induced autofluorescence using glutaraldehyde fixation has been used to enable imaging of proteins/organelles in the cell protoplast and to allow fluorescence imaging of fungal mycelium.

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“…They discovered that lignin was an AIE‐active biomaterial, mainly based on the clustering of carbonyl groups (C=O) and the restriction of intramolecular rotation (RIR) mechanism [stilbene (Ar−Cα=Cβ) and α‐carbonyl (Ar−Cα=O)]. They further confirmed the AIE behavior of lignosulfonate (LS) by testing the effect of cetyltrimethyl ammonium bromide (CTAB) on the fluorescence of LS and proposed that AIE might be the origin of lignin's fluorescence . This discovery provided a perspective to develop novel lignin‐based AIE‐active materials.…”

Section: Bioimagingmentioning

confidence: 99%

Lignin‐Based Micro‐ and Nanomaterials and their Composites in Biomedical Applications

Dai

et al. 2020

ChemSusChem

164

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Lignin, as the most abundant aromatic renewable biopolymer in nature, has long been regarded as waste and simply discarded from the pulp and paper industry. In recent years, with many breakthroughs in lignin chemistry, pretreatment, and processing techniques, a lot of the inherent bioactivities of lignin, including antioxidant activities, antimicrobial activities, biocompatibilities, optical properties, and metal‐ion chelating and redox activities, have been discovered and this has opened a new field not only for lignin‐based materials but also for biomaterials. In this Review, the biological activities of lignin and drug/gene delivery and bioimaging applications of various types of lignin‐based material are summarized. In addition, the challenges and limitations of lignin‐based materials encountered during the development of biomedical applications are also discussed.

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Aggregation-induced emission: the origin of lignin fluorescence

Abstract: Aggregation-induced emission plays a role in the origin of lignin fluorescence owing to the agglomeration of carbonyl groups and restriction of intramolecular rotation.

Cited by 84 publications

References 32 publications

Seeing biomass recalcitrance through fluorescence

Seeing biomass recalcitrance through fluorescence

Autofluorescence in Plants

Lignin‐Based Micro‐ and Nanomaterials and their Composites in Biomedical Applications

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