AIE gel exhibiting continuous gradient fluorescence based on a polar-responsive AIE-gen

Abstract

Traditional multicolor fluorescent hydrogels are generated through the assembly of discrete fluorescent hydrogels, which is not a complete integration much distinct from living organisms. On the basis of aggregation-induced emission (AIE), a special solvent polar-responsive AIE molecule possessing a twisted intramolecular charge transfer (TICT) effect was noticed. By incorporating it into the gel network, an AIE gel that displays continuous gradient fluorescence was fabricated. First, hydrogel A containing the solvent polar-responsive AIE-gen was prepared to show orange fluorescence. After soaking in the organic solvents, the fluorescence color transition of hydrogel A ranging from orange to green occurred when being immersed in high-polarity organic solvents ascribed to the embedded AIE-gen owning TICT effect. Then, hydrogel A was successively lifted up from organic solvents. Due to the different immersion time of each section for the hydrogel, the polarity difference occurred. Then, the produced gel B showed continuous gradient fluorescence ranging from orange to green under the irradiation of UV light.

Keywords

aggregation-induced emission / fluorescent hydrogel / multicolor / polar-responsiveness

References

[1] Prötzel D, Heß M, Scherz MD, Schwager M, Padje A, Glaw F. Widespread bone-based fluorescence in chameleons. Sci Rep. 2018;8(1):698.

[2] Freyer P, Stavenga DG. Biophotonics of diversely coloured peacock tail feathers. Faraday Discuss. 2020;223(233):49-62.

[3] Pratte ZA, Patin NV, McWhirt ME, Caughman AM, Parris DJ, Stewart FJ. Association with a sea anemone alters the skin microbiome of clownfish. Coral Reefs. 2018;37(4):1119-1125.

[4] Wei S, Qiu H, Shi H, et al. Promotion of color-changing luminescent hydrogels from thermo to electrical responsiveness toward biomimetic skin applications. ACS Nano. 2021;15(6):10415-10427.

[5] Wei S, Li Z, Lu W, et al. Multicolor fluorescent polymeric hydrogels. Angew Chem Int Ed. 2021;60(16):8608-8624.

[6] Chen F, Lin X, Li Y, Xu D, Qiu H, Yin S. Metallacycle-crosslinked supramolecular polymers constructed by amino–YNE click reaction with enhanced mechanical properties. Supramol Mater. 2022;1:100003.

[7] Wang Q, Qi Z, Wang Q-M, Chen M, Lin B, Qu D-H. A time-dependent fluorescent hydrogel for “time-lock” information encryption. Adv Funct Mater. 2022;32(49):2208865.

[8] Le X, Shang H, Yan H, et al. A urease-containing fluorescent hydrogel for transient information storage. Angew Chem Int Ed. 2021;60(7):3640-3646.

[9] Zhang H, Liu H, Hu Z, Ji X. Multicolor fluorescent supramolecular adhesive gels based on a single molecule with aggregation-induced ratiometric emission. Supramol Mater. 2022;1:100018.

[10] Li S, Ma J, Zhao X, et al. Highly fluorescence Ta₄C₃ MXene quantum dots as fluorescent nanoprobe for heavy ion detection and stress monitoring of fluorescent hydrogels. Chin Chem Lett. 2022;33(4):1850-1854.

[11] Lu W, Wei S, Shi H, et al. Progress in aggregation-induced emission-active fluorescent polymeric hydrogels. Aggregate. 2021;2(3):e37.

[12] Feng X, Wang C, Shang S, et al. Multicolor fluorescent cellulose hydrogels actuators: lanthanide-ligand metal coordination, synergetic color-changing and shape-morphing, and antibacterial activity. Chem Eng J. 2022;450:138356.

[13] Duan T, Bian Q, Li H. Protein hydrogels with reversibly patterned multidimensional fluorescent images for information storage. Biomacromolecules. 2022;23(7):3009-3016.

[14] Hai M, Zhang Q, Li Z, Cheng M, Kuehne AJC, Shi F. Visualizing polymer diffusion in hydrogel self-healing. Supramol Mater. 2022;1:100009.

[15] Zhang Y, Le X, Jian Y, Lu W, Zhang J, Chen T. 3D fluorescent hydrogel origami for multistage data security protection. Adv Funct Mater. 2019;29(46):1905514.

[16] Wu B-Y, Le X-X, Jian Y-K, et al. pH and thermo dual-responsive fluorescent hydrogel actuator. Macromol Rapid Commun. 2019;40(4):1800648.

[17] Sawayama J, Takeuchi S. Long-term continuous glucose monitoring using a fluorescence-based biocompatible hydrogel glucose sensor. Adv Healthcare Mater. 2021;10(3):2001286.

[18] Ghosh R, Goswami U, Ghosh SS, Paul A, Chattopadhyay A. Synergistic anticancer activity of fluorescent copper nanoclusters and cisplatin delivered through a hydrogel nanocarrier. ACS Appl Mater Interfaces. 2015;7(1):209-222.

[19] Jian Y, Wu B, Yang X, et al. Stimuli-responsive hydrogel sponge for ultrafast responsive actuator. Supramol Mater. 2022;1:100002.

[20] Liu H, Wei S, Qiu H, et al. Supramolecular hydrogel with orthogonally responsive R/G/B fluorophores enables multi-color switchable biomimetic soft skins. Adv Funct Mater. 2022;32(9):2108830.

[21] Zhang X, Wang B, Zheng Z, Yang G, Zhang C, Liao L. A robust photoswitchable dual-color fluorescent poly (vinyl alcohol) composite hydrogel constructed by photo-responsive FRET effect. Dyes Pigm. 2022;208:110800.

[22] Luo J, Xie Z, Lam JWY, et al. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun. 2001;18:1740-1741.

[23] Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ. Aggregation-induced emission: together we shine, united we soar. Chem Rev. 2015;115(21):11718-11940.

[24] Zhang J, He B, Hu Y, et al. Stimuli-responsive AIEgens. Adv Mater. 2021;33(32):2008071.

[25] Hu R, Leung NLC, Tang BZ. AIE macromolecules: syntheses, structures and functionalities. Chem Soc Rev. 2014;43(13):4494-4562.

[26] Li J, Wang J, Li H, Song N, Wang D, Tang BZ. Supramolecular materials based on AIE luminogens (AIEgens): construction and applications. Chem Soc Rev. 2020;49(4):1144-1172.

[27] Peng H-Q, Zheng X, Han T, et al. Dramatic differences in aggregation-induced emission and supramolecular polymerizability of tetraphenylethene-based stereoisomers. J Am Chem Soc. 2017;139(29):10150-10156.

[28] Peng H-Q, Liu B, Wei P, et al. Visualizing the initial step of self-assembly and the phase transition by stereogenic amphiphiles with aggregation-induced emission. ACS Nano. 2019;13(1):839-846.

[29] Wei B, Li W, Zhao Z, Qin A, Hu R, Tang BZ. Metal-free multicomponent tandem polymerizations of alkynes, amines, and formaldehyde toward structure- and sequence-controlled luminescent polyheterocycles. J Am Chem Soc. 2017;139(14):5075-5084.

[30] Li Z, Ji X, Xie H, Tang BZ. Aggregation-induced emission-active gels: fabrications, functions, and applications. Adv Mater. 2021;33(33):2100021.

[31] Zhang M, Saha ML, Wang M, et al. Multicomponent platinum(ii) cages with tunable emission and amino acid sensing. J Am Chem Soc. 2017;139(14):5067-5074.

[32] He B, Huang J, Zhang J, et al. Novel quinolizine AIE system: visualization of molecular motion and elaborate tailoring for biological application. Angew Chem Int Ed. 2022;61(11):e202117709.

[33] Yan D, Wang M, Wu Q, et al. Multimodal imaging-guided photothermal immunotherapy based on a versatile NIR-II aggregation-induced emission luminogen. Angew Chem Int Ed. 2022;61(27):e202202614.

[34] Xia Q, Zhang Y, Li Y, et al. A historical review of aggregation-induced emission from 2001 to 2020: a bibliometric analysis. Aggregate. 2022;3(1):e152.

[35] Cao S, Shao J, Abdelmohsen LKEA, Hest JCM. Amphiphilic AIEgen-polymer aggregates: design, self-assembly and biomedical applications. Aggregate. 2022;3(1):e128.

[36] Li JA, Zhou J, Mao Z, et al. Inside back cover: transient and persistent room-temperature mechanoluminescence from a white-light-emitting AIEgen with tricolor emission switching triggered by light (Angew Chem. Int. Ed. 22/2018). Angew Chem Int Ed. 2018;57(22):6705.

[37] Xu B, Song Z, Zhang M, et al. Controlling the thermally activated delayed fluorescence of axially chiral organic emitters and their racemate for information encryption. Chem Sci. 2021;12(47):15556-15562.

[38] Yang Y, Liang Y, Zheng Y, et al. Efficient and color-tunable dual-mode afterglow from large-area and flexible polymer-based transparent films for anti-counterfeiting and information encryption. Angew Chem Int Ed. 2022;61(23):e202201820.

[39] Wu Q, Li Y, Wang L, Wang D, Tang BZ. Aggregation-induced emission: an emerging concept in brain science. Biomaterials. 2022;286:121581.

[40] Xu Z, Zhang Z, Deng X, et al. Deep-brain three-photon imaging enabled by aggregation-induced emission luminogens with near-infrared-III excitation. ACS Nano. 2022;16(4):6712-6724.

[41] Sun J, Li H, Gu X, Tang BZ. Photoactivatable biomedical materials based on luminogens with aggregation-induced emission (AIE) characteristics. Adv Healthcare Mater. 2021;10(24):2101177.

[42] Jin H, Li H, Zhu Z, Huang J, Xiao Y, Yan Y. Hydration-facilitated fine-tuning of the AIE amphiphile color and application as erasable materials with hot/cold dual writing modes. Angew Chem Int Ed. 2020;59(25):10081-10086.

[43] Hu R, Lager E, Aguilar-Aguilar A, et al. Twisted intramolecular charge transfer and aggregation-induced emission of BODIPY derivatives. J Phys Chem C. 2009;113(36):15845-15853.

[44] Hu Y, Barbier L, Li Z, et al. Hydrophilicity-hydrophobicity transformation, thermoresponsive morphomechanics, and crack multifurcation revealed by AIEgens in mechanically strong hydrogels. Adv Mater. 2021;33(39):2101500.

[45] Grindy SC, Lenz M, Holten-Andersen N. Engineering elasticity and relaxation time in metal-coordinate cross-linked hydrogels. Macromolecules. 2016;49(21):8306-8312.

RIGHTS & PERMISSIONS

2023 The Authors. SmartMat published by Tianjin University and John Wiley & Sons Australia, Ltd.