journal article·2019-05-10Open access

Fabrication of Robust Spatially Resolved Photochromic Patterns on Cellulose Papers by Covalent Printing for Anticounterfeiting Applications

Guillaume Bretel, Erwan Le Grognec, Denis Jacquemin, Takashi Hirose, Kenji Matsuda, François-Xavier Felpin

ACS Applied Polymer Materials· Volume 1· Issue 5

Abstract

Despite its millennial age, cellulose paper remains the preferred material for domestic and professional printings, covering applications from simple office paperwork to fiducial solutions such as bills, passports, and head letters. The creation of robust photochromic patterns on cellulose papers for anticounterfeiting applications is an important and still partially unaddressed challenge. In this contribution, we report the covalent printing of dibenzothienylethenes as photochromic compounds through a spatially controlled light-mediated thiol–X ligations. Photophysical and theoretical studies provide evidence for a reversible photochromism behavior, not affected significantly by the polar environment of the cellulose matrix, and demonstrates a high fatigue resistance over 18 successive write–erase cycles. The strong coloration–discoloration switch can be easily followed by a direct naked-eye readout.
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Research context

OpenAlex topics: Photochromic and Fluorescence Chemistry · Polydiacetylene-based materials and applications · Luminescence and Fluorescent Materials

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

CNRS UMR 6230, CEISAM, Université de Nantes, F-44000 Nantes, France

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan

Funding

Centre National de la Recherche Scientifique · Japan Society for the Promotion of Science · Region des Pays de la Loire

References (43)

Show source-provided references
1. 10.1021/la301661x10.1021/la301661x ↗
2. 10.1021/bm401274v10.1021/bm401274v ↗
3. 10.1002/adma.20140100610.1002/adma.201401006 ↗
4. 10.1039/C5CC03902A10.1039/C5CC03902A ↗
5. 10.1002/adsc.20130069110.1002/adsc.201300691 ↗
6. 10.1021/jz502494810.1021/jz5024948 ↗
7. 10.1039/c1jm10543d10.1039/c1jm10543d ↗
8. 10.3390/molecules2001149510.3390/molecules20011495 ↗
9. 10.1002/anie.20160676010.1002/anie.201606760 ↗
10. 10.1039/c3ra00074e10.1039/c3ra00074e ↗
11. 10.1016/j.bios.2014.10.00610.1016/j.bios.2014.10.006 ↗
12. 10.1039/C5CC09889K10.1039/C5CC09889K ↗
13. 10.1039/C6CC02305C10.1039/C6CC02305C ↗
14. 10.1016/j.watres.2016.01.00810.1016/j.watres.2016.01.008 ↗
15. 10.1021/acssuschemeng.6b0276810.1021/acssuschemeng.6b02768 ↗
16. 10.1007/s10570-018-1833-010.1007/s10570-018-1833-0 ↗
17. 10.1038/ncomms404410.1038/ncomms4044 ↗
18. 10.1016/j.carbpol.2013.03.03210.1016/j.carbpol.2013.03.032 ↗
19. 10.1021/la404628p10.1021/la404628p ↗
20. 10.1039/C6RA17862F10.1039/C6RA17862F ↗
21. 10.15376/biores.11.4.8627-863710.15376/biores.11.4.8627-8637 ↗
22. 10.1016/j.carbpol.2016.05.00910.1016/j.carbpol.2016.05.009 ↗
23. 10.1021/acs.jpcc.6b0259410.1021/acs.jpcc.6b02594 ↗
24. 10.1039/C6RA23673A10.1039/C6RA23673A ↗
25. 10.1016/j.carbpol.2018.08.04210.1016/j.carbpol.2018.08.042 ↗
26. 10.1016/j.carbpol.2014.03.05110.1016/j.carbpol.2014.03.051 ↗
27. 10.1021/cr980069d10.1021/cr980069d ↗
28. 10.1021/cr500249p10.1021/cr500249p ↗
29. 10.1021/acsami.7b1482710.1021/acsami.7b14827 ↗
30. 10.1080/01960075.2010.49459410.1080/01960075.2010.494594 ↗
31. 10.1039/C7TC01081H10.1039/C7TC01081H ↗
32. 10.1021/acsomega.8b0131710.1021/acsomega.8b01317 ↗
33. 10.1055/s-0036-158879610.1055/s-0036-1588796 ↗
34. 10.1016/j.chroma.2006.02.09610.1016/j.chroma.2006.02.096 ↗
35. 10.1002/chem.20140373610.1002/chem.201403736 ↗
36. 10.1002/ajoc.20120017910.1002/ajoc.201200179 ↗
37. Frisch, M. J. Gaussian 16, A.0.3; Gaussian Inc.: Wallingford, CT, 2016.
38. 10.1063/1.47852210.1063/1.478522 ↗
39. 10.1002/jcc.2175910.1002/jcc.21759 ↗
40. 10.1021/cr990400910.1021/cr9904009 ↗
41. 10.1002/chem.20140629910.1002/chem.201406299 ↗
42. 10.1039/C7CP06541H10.1039/C7CP06541H ↗
43. 10.1021/la503388j10.1021/la503388j ↗