Volume 40 Issue 7
Apr.  2023
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Article Contents
WU Ping, REN Hong. Research progress of water responsive compound material in the field of green writing and anti-counterfeiting[J]. Acta Materiae Compositae Sinica, 2023, 40(7): 3824-3836. doi: 10.13801/j.cnki.fhclxb.20230103.003
Citation: WU Ping, REN Hong. Research progress of water responsive compound material in the field of green writing and anti-counterfeiting[J]. Acta Materiae Compositae Sinica, 2023, 40(7): 3824-3836. doi: 10.13801/j.cnki.fhclxb.20230103.003

Research progress of water responsive compound material in the field of green writing and anti-counterfeiting

doi: 10.13801/j.cnki.fhclxb.20230103.003
Funds:  National Natural Science Foundation of China (22106051); The Project of Education Department of Jilin Province (JJKH20210240KJ); The Major Project of Jilin Institute of Chemical Technology (2019014)
  • Received Date: 2022-11-07
  • Accepted Date: 2022-12-15
  • Rev Recd Date: 2022-12-05
  • Available Online: 2023-01-03
  • Publish Date: 2023-07-15
  • Water stimulus responsive materials can undergo reversible color or fluorescence emission change process under the external stimulus of water. Because of its low cost, non-toxic, compatibility with existing inkjet printing technology and other advantages, it is an ideal choice to achieve rewritable. Meanwhile, it shows great application potential in information storage, security and anti-counterfeiting. In this review, the research progress of water responsive compound material based on organic small molecules in the past five years is systematically reviewed. Inductive materials are classified from the viewpoints of water induced proton transfer, water induced configuration change, water induced proton transfer combined with configuration change sensing principle. The achievements and technologies in design principles, optical physical properties and information storage applications are summarized. It is hoped to provide ideas for further developing the application of water responsive composites in the field of green writing and anti-counterfeiting, promoting the development of related industries.


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  • [1]
    WANG Y Y, ZHANG Y M, ZHANG S X A. Stimuli-induced reversible proton transfer for stimuli-responsive materials and devices[J]. Accounts of Chemical Research,2021,54(9):2216-2226. doi: 10.1021/acs.accounts.1c00061
    KHAZI M I, JEONG W, KIM J M. Functional materials and systems for rewritable paper[J]. Advanced Materials,2018,30(15):1705310. doi: 10.1002/adma.201705310
    QIN T, SHENG L, ZHANG S X A. Highly tunable multicolor water-jet rewritable paper based on simple new-type dual addressable oxazolidines[J]. ACS Applied Material & Interfaces,2018,10(47):40838-40843. doi: 10.1021/acsami.8b13660
    GARCIA-AMOROS J, SWAMINATHAN S, RAYMO F M. Saving paper with switchable ink[J]. Dyes and Pigments,2014,106:71-73. doi: 10.1016/j.dyepig.2014.02.019
    GONTANI S, OHASHI T, MIYANAGA K, et al. Structural comparison of two bisphenol S derivatives used as colour developers in high-performance thermal paper[J]. Dyes and Pigments,2017,139:549-555. doi: 10.1016/j.dyepig.2016.12.049
    WANG W T, ZHOU Y C, YANG L, et al. Stimulus-responsive photonic crystals for advanced security[J]. Advance Functional Materials,2022,32(40):2204744. doi: 10.1002/adfm.202204744
    WANG H H, SUN L Y. Materials and society: Functional chemicals and materials in banknote and security paper[J]. Accounts of Materials Research,2021,2(1):1-6. doi: 10.1021/accountsmr.0c00071
    YOON B, SHIN H, KANG E M, et al. Inkjet-compatible single-component polydiacetylene precursors for thermochromic paper sensors[J]. ACS Applied Materials & Interfaces,2013,5(11):4527-4535. doi: 10.1021/am303300g
    GARAI B, MALLICK A, BANERJEE R. Photochromic metal-organic frameworks for inkless and erasable printing[J]. Chemistry Science,2016,7(3):2195-2200. doi: 10.1039/C5SC04450B
    MA Y, SHEN L, SHE P F, et al. Constructing multi-stimuli-responsive luminescent materials through outer sphere electron transfer in ion pairs[J]. Advanced Optical Materials,2019,7(8):1801657. doi: 10.1002/adom.201801657
    YANG G J, DING J L, YANG B G, et al. Highly stretchable electrochromic hydrogels for use in wearable electronic devices[J]. Journal of Materials Chemistry,2019,7(31):9481-9486. doi: 10.1039/c9tc02673h
    ZHANG W R, ZHANG Y M, XIE F L, et al. A single-pixel RGB device in a colorful alphanumeric electrofluorochromic display[J]. Advance Materials,2020,32(37):2003121. doi: 10.1002/adma.202003121
    ZHANG T, SHENG L, LIU U N, et al. Photoinduced proton transfer between photoacid and pH-sensitive dyes: Influence factors and application for visible-light-responsive rewritable paper[J]. Advance Functional Materials,2018,28(16):1705532. doi: 10.1002/adfm.201705532
    DU J H, SHENG L, CHEN Q N, et al. Simple and general platform for highly adjustable thermochromic fluorescent materials and multi-feasible applications[J]. Materials Horizons,2019,6(8):1654-1662. doi: 10.1039/C9MH00253G
    LIU S Y, MA Y, LIU S J, et al. Achieving multiple emission states and controllable response behavior in thermochromic luminescent materials for security applications[J]. Journal of Materials Chemistry C,2020,8(31):10798-10804. doi: 10.1039/C9TC06627F
    HAI J, WANG H, SUN P P, et al. Smart responsive luminescent aptamer-functionalized covalent organic framework hydrogel for high-resolution visualization and security protection of latent fingerprints[J]. ACS Applied Materials & Interfaces,2019,11(47):44664-44672. doi: 10.1021/acsami.9b18251
    YU X Y, WU L Z, YANG D, et al. Hydrochromic CsPbBr3 nanocrystals for anti-counterfeiting[J]. Angewandte Chemie-International Edition,2020,59(34):14527-14532. doi: 10.1002/anie.202005120
    佘鹏飞. 智能响应型光功能材料的设计、合成及其在可擦除与安全打印中的应用研究[D]. 南京: 南京邮电大学, 2020.

    SHE Pengfei. The design and synthesis of smart responsive optical functional materials for rewritable and security printing[D]. Nanjin: Nanjing University of Posts and Telecommunications, 2020(in Chinese).
    MA Y, YU Y X, LI J G, et al. Stimuli-responsive photofunctional materials for green and security printing[J]. InfoMat,2021,3(1):82-100. doi: 10.1002/inf2.12125
    KUMAR P, SAKLA R, GHOSH A, et al. A reversible colorimetric sensor for moisture detection in organic solvents and application in ink-less writing[J]. ACS Applied Materials & Interfaces,2017,9(30):25600-25605. doi: 10.1021/acsami.7b05335
    WU P, REN H. Azobenzene with sulfonamide group deprotonated by green developer for moisture detection and water jet rewritable paper[J]. Dyes and Pigments,2021,196:109764. doi: 10.1016/j.dyepig.2021.109764
    YANG X F, ZHU F Q, LI Y X, et al. Three indole derived azo-azomethine dyes as effective chemosensors for F ion and trace water detection[J]. Bulletin of the Chemical Society of Japan,2021,93(7):870-879. doi: 10.1246/bcsj.20200003
    DONG C, HAO J C. Synthesis of a new functionalized phenol and use as ink-free rewriting[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects,2019,583:123856. doi: 10.1016/j.colsurfa.2019.123856
    NANDI S K, HALDAR D. 1-m-nitrobenzoyl semicarbazide: Reversible colorimetric cascade indicators for fluoride and moisture[J]. New Journal of Chemistry,2020,44(40):17523-17530. doi: 10.1039/D0NJ03769A
    CHO E, LEE T S. Manipulation of intramolecular hydrogen bonds in single-benzene derivatives: Esterase sensing, fluorescence patterning, and inkless writing[J]. Sensors & Actuators B: Chemical,2020,319:128307. doi: 10.1016/j.snb.2020.128307
    XI G, SHENG L, ZHANG I, et al. Endowing hydrochromism to fluorans via bioinspired alteration of molecular structures and microenvironments and expanding their potential for rewritable paper[J]. ACS Applied Materials & Interfaces,2017,9(43):38032-38041. doi: 10.1021/acsami.7b12363
    JU L, GAO W B, ZHANG J Y, et al. A new absorption/fluorescence dual-mode hydrochromic dye for water-jet printing and anti-counterfeiting applications[J]. Journal of Materials Chemistry C,2020,8(8):2806-2811. doi: 10.1039/C9TC06522A
    卫小燕, 张金艳, 盛兰, 等. Off-on/on-off 双模式水致变色材料: 水诱导微环境酸度改变调控罗丹明衍生物颜色切换[J]. 应用化学, 2022, 39(7):1119-1128.

    WEI Xiaoyan, ZHANG Jinyan, SHENG Lan, et al. Off-on/on-off dual-mode hydrochromic materials: Water-induced acidity changes in the microenvironment regulate the color switching of rhodamine derivatives[J]. Chinese Journal of Applied Chemistry,2022,39(7):1119-1128(in Chinese).
    QIN T Y, HAN J Q, GENG Y, et al. A multi-addressable dyad with switchable cyan/magenta/yellow colors for full color rewritable papers[J]. Chemistry A European Journal,2018,24(48):12448. doi: 10.1002/chem.201803545
    ZHAO H Q, QIN X C, ZHAO L, et al. Invisible inks for secrecy and anticounterfeiting: From single to double-encryption by hydrochromic molecules[J]. ACS Applied Materials & Interfaces,2020,12(7):8952-8960. doi: 10.1021/acsami.0c00462
    SHENG L, LI M J, ZHU S Y, et al. Hydrochromic molecular switches for water-jet rewritable paper[J]. Nature Communications,2014,5:3044. doi: 10.1038/ncomms4044
    KARIMIPOUR K, KEYVAN RAD J, GHOMI A R, et al. Hydrochromic and photoswitchable polyacrylic nanofibers containing spiropyran in eco-friendly ink-free rewriteable sheets with responsivity to humidity[J]. Dyes and Pigments,2020,175:108185. doi: 10.1016/j.dyepig.2020.108185
    李建华, 王洪泽, 盛兰, 等. 无墨喷水可重复打印纸工业化制备[J]. 应用化学, 2018, 35(6):679-686. doi: 10.11944/j.issn.1000-0518.2018.06.170142

    LI Jianhua, WANG Hongze, SHEN Lan, et al. Industrial preparation of water jet rewritable paper[J]. Chinese Journal of Applied Chemistry,2018,35(6):679-686(in Chinese). doi: 10.11944/j.issn.1000-0518.2018.06.170142
    高文彬. 基于吲哚并噁唑啉的水致变色材料的开发及应用[D]. 长春: 吉林大学, 2019.

    GAO Wenbin. The development and application of hydrochromic material based on indolino-oxazolidine[D]. Changchun: Jilin University, 2019(in Chinese).
    盛兰, 席冠, 张晓安, 等. 一种可重复使用的水写纸: 中国专利, ZL 201510824186[P]. 2017-07-28.

    SHEN Lan, XI Guan, ZHANG Xiaoan, et al. A reusable water writing pape: Chinese patent, ZL 201510824186[P]. 2017-07-28(in Chinese).
    XI G, SHENG L, DU J H, et al. Water assisted biomimetic synergistic process and its application in water-jet rewritable paper[J]. Nature Communications,2018,9:4819. doi: 10.1038/s41467-018-07211-z
    SUN H, SUN S S, HAN F F, et al. Water-stimuli-responsive dynamic fluorescent switch from Kasha's rule to anti-Kasha's rule based on a tetraphenylethene substituted Schiff base[J]. Chemical Engineering Journal,2021,405:127000. doi: 10.1016/j.cej.2020.127000
    MA Y, SHE P F, ZHANG K Y, et al. Dynamic metal-ligand coordination for multicolour and waterjet rewritable paper[J]. Nature Communications,2018,9:3. doi: 10.1038/s41467-017-02452-w
    SAKAI R, BARASA E B, SAKAI N, et al. Colorimetric detection of anions in aqueous solution using poly(phenylacetylene) with sulfonamide receptors activated by electron withdrawing group[J]. Macromolecules,2012,45(20):8221-8227. doi: 10.1021/ma301767g
    KUMAR P, KAUSHIK R, GHOSH A, et al. Detection of moisture by fluorescent OFF-ON sensor in organic solvents and raw food products[J]. Analytical Chemistry,2016,88(23):11314-11318. doi: 10.1021/acs.analchem.6b03949
    YOON S A, HYUN OH J, KIM S K, et al. Water-sensitive ratiometric fluorescent probes and application to test strip for rapid and reversible detection of water[J]. Dyes and Pigments,2019,165:421-428. doi: 10.1016/j.dyepig.2019.02.052
    YOO H, KIM H S. Real-time colorimetric water content monitoring of organic solvents by an azo dye incorporated into AlPO4-5 nanochannel[J]. Journal of Materials Chemistry C,2019,7(24):7336-7343. doi: 10.1039/C9TC01767D
    WU Y C, JI J Q, ZHOU Y B, et al. Ratiometric and colorimetric sensors for highly sensitive detection of water in organic solvents based on hydroxyl-containing polyimide fluoride complexes[J]. Analytica Chimica Acta,2020,1108:37-45. doi: 10.1016/j.aca.2020.02.043
    WANG J, ZHANG X M, LIU H B. Highly sensitive pyrene-dansyl conjugate-based fluorescent sensor for discriminative detection of water in organic solvents[J]. Dyes and Pigments,2020,182:108685. doi: 10.1016/j.dyepig.2020.108685
    HUANG J, LIANG Y H, LIU H B, et al. N-hydroxypropyl substituted 4-hydroxynaphthalimide: Differentiation of solvents and discriminative determination of water in organic solvents[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2021,253:119559. doi: 10.1016/j.saa.2021.119559
    WU P, REN H, HAN D D, et al. Effects of chemical equilibrium on Cu2+ colorimetric probe based on azobenzene with ortho amino and sulfonamide group[J]. Journal of Molecular Structure,2021,1244:130959. doi: 10.1016/j.molstruc.2021.130959
    WU F Y, WANG L Y, TANG H, et al. 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[J]. Analyst Chemistry,2019,91(8):5261-5269. doi: 10.1021/acs.analchem.9b00032
    TAN J Y, WANG X Y, ZHANG Q, et al. Chalcone based ion-pair recognition towards nitrates and the application for the colorimetric and fluorescence turn-on determination of water content in organic solvents[J]. Sensors and Actuators B: Chemical,2018,260:727-735. doi: 10.1016/j.snb.2017.12.186
    KUMAR P, GHOSH A, JOSE D A. Chemical sensors for water detection in organic solvents and their applications[J]. ChemistrySelect,2021,6(4):820-842. doi: 10.1002/slct.202003920
    PAPAZOI E, DOUVSLI A, DIAMANTIS S A, et al. Unravelling the mechanism of water sensing by the Mg2+ dihydroxy-terephthalate MOF (AEMOF-1')[J]. Molecular Systems Design & Engineering,2020,5(2):461-468. doi: 10.1039/c9me00098d
    WU P, REN H, HAN D D, et al. The colorimetric sensor based on azobenzenes with sulfonamide group for fluorine ion and moisture detection in organic solvents[J]. ChemistrySelect,2022,7(23):e202200992. doi: 10.1002/slct.202200992
    KUMAR P, GHOSH A, JOSE D A. A simple colorimetric sensor for the detection of moisture in organic solvents and building materials: Applications in rewritable paper and fingerprint imaging[J]. Analyst,2019,144(2):594-601. doi: 10.1039/C8AN01042K
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