Research progress on the luminescence of biomacromolecules

doi:10.1016/j.jmst.2020.11.009

Abstract

Abstract:

Luminescent materials show great potential in various applications. Traditional aggregation-induced emission (AIE) luminogens are mostly produced by complex organic synthesis and have poor hydrophilicity and biocompatibility, which limit their practical applications. Therefore, it is of great significance to develop fluorescent materials with good hydrophilicity and biocompatibility, and biomacromolecules with these properties have attracted our attention. Partial biomacromolecules can generate unique new fluorophores during the gelation process to obtain hydrogels with good fluorescence properties. In addition, biomacromolecules can be modified with fluorescent groups to obtain fluorescent materials with excellent performance, thus improving the hydrophilicity and biocompatibility of fluorophore. In particular, grafting aggregation-caused quenching (ACQ) luminogens onto biomacromolecules can even effectively inhibit the aggregation and self-quenching of luminogens. It is well known that aromatic biological macromolecules such as green fluorescent protein have intrinsic fluorescence. Intrinsic fluorescence is also observed in nonaromatic biological macromolecules without traditional chromophores such as chitosan, cellulose and sodium alginate. The luminescence of nonaromatic biomacromolecule can be rationalized by the clustering-triggered emission (CTE) mechanism, namely, clustering of nonconventional chromophores and subsequent electron overlap and conformation rigidification are accountable for the emssion. In this review, fluorescence gels obtained from biomacromolecules, biomacromolecules modified with fluorophores, and the intrinsic luminescence of biomacromolecular luminogens are assessed. This review will help to develop low-cost, biocompatible luminescent materials and has great significance for comprehending the luminescence of nonconventional luminophores and expanding the application of luminescent compounds.

Key words: Biomacromolecules, Fluorescent gels, Graft, Intrinsic fluorescence, Clustering-Triggered emission

Dandan Wang, Junping Ju, Shuang Wang, Yeqiang Tan. Research progress on the luminescence of biomacromolecules[J]. J. Mater. Sci. Technol., 2021, 76: 60-75.

Figures/Tables 16

Fig. 1. (a) The synthetic route to TPEDMesB [13]. Copyright 2011, The Royal Society of Chemistry. (b) The synthesis of TPPA-DBO probe [14]. Copyright 2016, The Royal Society of Chemistry. (c) Synthetic route to Im-TPE [15]. Copyright 2011, The Royal Society of Chemistry.

Fig. 2. (a) Photograph of the rice taken under 365 nm UV light illumination and emission spectrum. (b) Photographs of the solutions of starch, cellulose and BSA taken at room temperature, and 77 K under room lighting. (c) Photographs of the solid powders of starch, cellulose and BSA taken under 365 nm UV illumination at room temperature [22]. Copyright 2013, Science China Press and Springer-Verlag GmbH.

Fig. 3. LSCM images of (a) selectively reduced CG microspheres excited at 365 nm, (b) CG microspheres excited at 488 nm, and (c) chitosan microspheres crosslinked by formaldehyde (CF microspheres) excited at 543 nm. The scale bars represent 10um [16]. Copyright 2007, Wiley-VCH. (d) UV-vis absorption (black line) spectrum of the 3D-FCH. Inset: photograph of the 3D-FCH under sunlight (top) and UV light (365 nm) (bottom). (e) fluorescence excitation and emission spectra (λex = 37 nm, λem = 401 nm) [17]. Copyright 2015, The Royal Society of Chemistry (f) Chitosan-GA cross-linking reaction [18]. Copyright 2018, American Chemical Society. (g) The schematic of gelation process of the as-developed BSA protein hydrogel. (h) Fluorescence photographs of 20 % BSA solution and 20 % BSA hydrogel excited by 365, 405, 420, and 490 nm, respectively [47]. Copyright 2018, Wiley-VCH.

Fig. 4. (a) Schematic diagram of chitosan-based fluorescent materials: “Molecule’’ to “Material’’ [19]. Copyright 2012, Elsevier B.V. (b) Synthesis of a Bioconjugate of Tetraphenylethene(TPE) and Chitosan (CS). (c) Fluorescent images of TPE - CS [48]. Copyright 2013, American Chemical Society. (d) Confocal laser scanning fluorescence microscope images of the gelation process of TPE-CS [49]. Copyright 2016, Nature Publishing Group. (e) Schematic representation of a reaction mechanism between the CHI oligomer and FITC. Schematic representation of the reaction mechanism between CHI-FITC and Cu2+ (f) and the energy transfer phenomenon (g) [50]. Copyright 2017, MDPI, ST ALBAN-ANLAGE.

Fig. 5. (a) Schematic representetion of the detection of the anthrax biomarker (dipicolinic acid, DPA) and fluorescence images of the sensor dispersed in aqueous solution before (left) and after (right) the addition of 0.1 mM DPA under a UV lamp [51]. Copyright 2018, Elsevier Ltd. (b) The mechanisms of the shape memory hydrogels with simultaneously switchable fluorescence [52]. Copyright 2018, WILEY-VCH.

Fig. 6. (a) Schematic illustration of the fluorescent functionalization of cellulose [53]. Copyright 2010 Wiley Periodicals, Inc. (b) Synthetic route and images under visible light (left) and UV irradiation (right, 365 nm) of various cellulose-based fluorescent powders prepared from different cellulose derivatives. (c) synthetic route of CA-FITC and images under visible light (top) and UV irradiation (bottom, 365 nm) of two different CA-FITC powders obtained in neutral (i, methanol) and alkaline (ii, NaOH/H2O/methanol solutions) precipitants, respectively [20]. Copyright 2016, WILEY-VCH. (d) Chemical composition of the cellulose-based trichromatic solid fluorescent materials (CA-SP, CA-FITC, and CA-Pyr), and their fluorescent images change with the length of UV irradiation (365 nm) [21]. Copyright 2017, WILEY-VCH.

Fig. 7. (a) Synthesis of the Fluorescent Cellulose Derivatives AC-AET-DMANMs [55]. Copyright 2017, American Chemical Society. (b) Synthetic scheme of fluorescent coumarin-grafted alginate. (c) Macroscopic appearance of the functionalized alginate [56]. Copyright 2020, The Royal Society of Chemistry.

Fig. 8. (a) The tertiary structure of GFP: carbon atoms are shown in white, nitrogen in blue and oxygen in red [67]. Copyright 2009, The Royal Society of Chemistry. (b) Chromophore structures of BFP derivatives, CFP derivatives, EGFP derivatives and YFP derivatives [63]. Copyright 2009, The Royal Society of Chemistry.

Fig. 9. (a) Confocal microscopy images of the poly(ValGlyGlyLeuGly) amyloidlike fibrils [71]. Copyright 2007, National Academy of Sciences. (b, c) Fluorescence microscopy images of (b) fully hydrated and (c) dry GVA fibrils [72]. Copyright 2011, American Chemical Society.

Fig. 10. (a) Exampled nonaromatic amino acids and photographs of their recrystallized solids taken under 365 nm UV light. (b) Photographs of different ε-PLL aqueous solutions and solid powders taken under 365 nm UV light or after ceasing the UV irradiation [73]. Copyright 2018, Science China Press and Springer-Verlag GmbH.

Fig. 11. (a) N?O and O?O intermolecular interactions around one molecule. (b) fragmental 3D through space electronic communication channel in the l-Ser crystals (color online) [73]. Copyright 2018, Science China Press and Springer-Verlag GmbH.

Fig. 12. (a) Representation of native human serum albumin structure and schematic representation of fibril formation via intermediate oligomers. (b) Changes in the fluorescence spectra (λex = 375 nm) of HSA as a function of concentrations (2-500 μM) at 450 nm emission wavelength [74]. Copyright 2017, American Chemical Society. (c) BSA structure with partial aromatic (green, cyan, and blue) and nonaromatic (purple and yellow) amino acid residues shown in different colors [75]. Copyright 2019, Wiley-VCH.

Fig. 13. (a) Photographs of the solid powder and a tablet of BSA placed in air or in vacuum taken under 312 nm UV light or after ceasing the irradiation. (b, c) Emission spectra of BSA powder (b) and tablet (c) with varying λex values. (d) Absorption and delayed emission spectra of a BSA tablet in air with varying λex values. (e) Excitation spectra of a BSA tablet with different λem values. (f) Demonstration of the potential anticounterfeiting and oxygen sensing applications of BSA [75]. Copyright 2019, Wiley-VCH.

Fig. 14. (a) Photographs taken under 365 nm UV light of varying aqueous GMr solutions. (b) Schematic illustration of SA molecules from isolated to aggregated states and possible intra- and intermolecular interactions within the clusters. (c) Photographs of a flower drawn on a PTFE plate using 8 wt % GM r taken at ambient conditions under room light, 312 nm UV light, and after the stop of UV irradiation [23]. Copyright 2018, American Chemical Society.

Fig. 15. (a) Photographs of CMC-Na and CMC-Zn powders under ambient conditions taken at different time intervals before and after the excitation was turned off (λex =365 nm) [85]. Copyright 2018, Elsevier Ltd. (b) Photographs of MCC, HEC, HPC, and CA powders taken under 365 nm UV irradiation [86]. Copyright 2019, Frontiers Media S.A. (c) Fluorescence spectra of CS-1 solution (1 mg mL-1) with different excitation wavelengths. Fluorescence microscope images of CS-1 solid powder. 1, 2, and 3 refer to images taken under UV (340-380), blue (460-500), and green (540-552) lights, respectively (Scale bar 500 μm) [89]. Copyright 2020, Elsevier Ltd.

Fig. 16. Comparison of PL intensity for different concentrations of CMCh and CS solutions before and after mixing with 0.005 M of Zn2+ at pH = 6.4. The λex used for pure CMCh and CS solutions is 320 nm, and is 358 nm for CMCh-Zn and CS-Zn solutions [93]. Copyright 2020, Elsevier Ltd.

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