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

WU Ping; REN Hong

doi:10.13801/j.cnki.fhclxb.20230103.003

Volume 40 Issue 7

Apr. 2023

Turn off MathJax

Article Contents

Article Navigation > Acta Materiae Compositae Sinica > 2023 > 40(7): 3824-3836

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

Citation:

PDF( 9250 KB)

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

doi: 10.13801/j.cnki.fhclxb.20230103.003

WU Ping,
REN Hong^,

School of Chemical and Pharmaceutical Engineering, Jilin Institute of Chemical Technology, Jilin 132022, China

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

Abstract

Abstract

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.
- responsive compound material,
- organic small molecule,
- green writing,
- anti-counterfeiting,
- proton transfer,
- configuration change
Long Abstrsct
Innovation Points

FullText(HTML)

References(52)

References

[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
[2]	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
[3]	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
[4]	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
[5]	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
[6]	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
[7]	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
[8]	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
[9]	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
[10]	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
[11]	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
[12]	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
[13]	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
[14]	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
[15]	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
[16]	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
[17]	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
[18]	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).
[19]	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
[20]	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
[21]	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
[22]	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
[23]	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
[24]	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
[25]	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
[26]	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
[27]	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
[28]	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).
[29]	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
[30]	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
[31]	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
[32]	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
[33]	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
[34]	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).
[35]	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).
[36]	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
[37]	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
[38]	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
[39]	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
[40]	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
[41]	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
[42]	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
[43]	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
[44]	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
[45]	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
[46]	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
[47]	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
[48]	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
[49]	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
[50]	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
[51]	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
[52]	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