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New Journal of Chemistry
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ARTICLE
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THF and 20 mL deionized water. Pd(Ph3P)4 was added under
nitrogen. The reaction was refluxed overnight. The solvent was
removed by evaporation. 40 mL water was added and extracted
three times with diethyl ether, and then dried over anhydrous
sodium sulfate. The solvent was removed by evaporation and
the product was then purified by column chromatography to
get white solid. Yield: 38%. 1H NMR (500 MHz, DMSO-d6) δ 10.82
(d, J = 4.9 Hz, 2H), 10.28 (d, J = 7.7 Hz, 2H), 7.89 (t, J = 3.7 Hz,
2H), 7.84-7.75 (m, 2H), 7.45 (dd, J = 17.8, 8.0 Hz, 4H), 7.24-6.89
(m, 16H). MALDI-TOF-MS (m/z): calcd for C40H28O4, 572.19;
found [M-H]+ 570.96.
STS: CHO-TPE-CHO (0.5 g, 0.87 mmol) and Indole-SO3 (0.5 g, 1.8
mmol) were dissolved in 25 mL ethanol. The reaction was
refluxed overnight. The mixture was purified by column
chromatography after adding triethylamine. The product was
added to hydrochloric acid methanol solution. The solvent was
removed by evaporation and then washed with water to get red
powder. Yield: 52%. 1H NMR (500 MHz, DMSO-d6) δ 11.26 (d, J
= 11.5 Hz, 2H), 8.60 (dd, J = 16.3, 8.4 Hz, 2H), 8.52-8.44 (m, 2H),
8.09-7.95 (m, 4H), 7.91-7.77 (m, 4H), 7.76-7.56 (m, 8H), 7.12
(dddd, J = 37.1, 29.6, 13.1, 7.3 Hz, 16H), 4.82 (q, J = 7.7, 7.0 Hz,
4H), 2.63 (q, J = 6.0 Hz, 4H), 2.19 (p, J = 7.7, 6.9 Hz, 4H), 1.78 (d,
J = 11.5 Hz, 12H). 13C NMR (126 MHz, DMSO-d6) δ 182.45,
159.21, 149.66, 144.03, 143.83, 142.52, 141.37, 140.79, 137.02,
134.11, 131.74, 131.28, 129.61, 128.34, 128.09, 127.07, 126.25,
123.45, 122.05, 117.65, 115.60, 112.64, 52.44, 47.76, 46.05,
26.83, 25.06. LC-HRMS (ESI, m/z): calcd for C68H62N2O8S2,
1098.39; found [M-H]+ 1097.37, [M-2H]2+/2 548.18. FTIR (KBr,
cm-1) O-H: 3448.155; Ar-C: 1587.154, 1521.585, 1467.587; C-N:
1305.593; S=O: 1170.599, 576.621.
DOI: 10.1039/D1NJ01637G
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
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We gratefully acknowledge financial support from the National
Natural Science Foundation of China (51303063).
Notes and references
1
2
3
A. P. de Silva, D. B. Fox, T. S. Moody and S. M. Weir, Trends in
Biotechnology, 2001, 19, 29–34.
S. Lin, K. G. Gutierrez-Cuevas, X. Zhang, J. Guo and Q. Li, Adv.
Funct. Mater., 2021, 31, 2007957.
T. Komatsu, K. Johnsson, H. Okuno, H. Bito, T. Inoue, T.
Nagano and Y. Urano, J. Am. Chem. Soc., 2011, 133, 6745–
6751.
4
5
B. Prusti, H. Aggarwal and M. Chakravarty, ChemPhotoChem,
2020, 4, 347–356.
S. Goswami, K. Aich, S. Das, A. K. Das, D. Sarkar, S. Panja, T. K.
Mondal and S. Mukhopadhyay, Chem. Commun., 2013, 49
10739.
,
6
7
8
9
K. Aich, S. Goswami, S. Das, C. D. Mukhopadhyay, C. K. Quah
and H.-K. Fun, Inorg. Chem., 2015, 54, 7309–7315.
L. Zhang, Y. Zhang, M. Wei, Y. Yi, H. Li and S. Yao, New J. Chem.,
2013, 37, 1252.
S. Tang, Y. Zhang, P. Dhakal, L. Ravelo, C. Anderson, K. Collins
and F. Raymo, J. Am. Chem. Soc., 2018, 140, 4485–4488.
J. M. Park, S. H. Nam, K.-I. Hong, Y. E. Jeun, H. S. Ahn and W.-
D. Jang, Sensors and Actuators B: Chemical, 2021, 332, 129534.
RSTRS: STS was dissolved in methanol, and then added K2CO3.
After removing excess K2CO3, RSTRS was obtained by removing
10 A. Kundu, P. S. Hariharan, K. Prabakaran, D. Moon and S. P.
Anthony, RSC Adv., 2015, , 98618–98625.
11 N. R. Paisley, C. M. Tonge and Z. M. Hudson, Front. Chem.,
2020, , 229.
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solvent. Yield: 97%. H NMR (500 MHz, Methanol-d4) δ 7.37-
8
7.25 (m, 8H), 7.17-7.05 (m, 12H), 7.05-6.99 (m, 6H), 6.96 (t, J =
10.1 Hz, 2H), 6.76 (t , 2H), 6.68-6.61 (m, 4H), 5.82 (dd, 2H), 3.29
(m, 4H), 2.82 (m, 4H), 2.16-2.04 (m, 4H), 1.27 (d, J = 5.6 Hz, 6H),
1.15 (d, J = 4.9 Hz, 6H).
12 T. Lin, X. Su, K. Wang, M. Li, H. Guo, L. Liu, B. Zou, Y.-M. Zhang,
Y. Liu and S. X.-A. Zhang, Mater. Chem. Front., 2019, 3, 1052–
1061.
13 L. Ju, W. Gao, J. Zhang, T. Qin, Z. Du, L. Sheng and S. X.-A.
Zhang, J. Mater. Chem. C, 2020,
8, 2806–2811.
14 C. S. Wijesooriya, J. A. Peterson, P. Shrestha, E. J. Gehrmann,
4.3. Preparation and processing of STS/PVP film
A. H. Winter and E. A. Smith, Angew. Chem. Int. Ed., 2018, 57
12685–12689.
,
The film is prepared by adding PVP (398 mg, Mn: 40000) and
STS (2 mg) to methanol (3 mL), stirring and dissolving, then
adding 5% volume fraction of sulfuric acid methanol solution 12
μL to the mixed solution. The 100 μL mixed solution was coated
on the quartz plate to form a square of about 1.3 cm × 1.3 cm,
and the orange film was obtained. The film thickness was
measured many times, and the film thickness range was about
12.64-19.78 μm. The blue light irradiation process is at a
distance of 0.5 cm and a temperature of 50 °C .
15 H. Cheng, P. Ma, Y. Wang, G. Hu, S. Fang, Y. Fang and Y. Lin,
Chem. Asian J., 2017, 12, 248–253.
16 P. Xue, T. Zhang and Y. Han, J. Mater. Chem. C, 2019, 7, 9537-
9544.
17 M.-Q. Zhu, G.-F. Zhang, C. Li, M. P. Aldred, E. Chang, R. A.
Drezek and A. D. Q. Li, J. Am. Chem. Soc., 2011, 133, 365–372.
18 J. Ji, T. Wu, Y. Zhang and F. Feng, ACS Appl. Mater. Interfaces,
2019, 11, 15222–15232.
19 O. V. Chashchikhin, M. F. Budyka, T. N. Gavrishova and P. A.
Nikulin, Chem. Phys. Lett., 2018, 696, 135–138.
20 T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai and M. Irie, J. Am.
Chem. Soc., 2004, 126, 14843–14849.
21 2 C. Yun, J. You, J. Kim, J. Huh and E. Kim, J. Photochem.
Photobiol., C, 2009, 10, 111–129.
4.4. Acid/alkali fumigation of the encrypted information
The process of acid fumigation of the encrypted information is
by placing it in HCl gas. HCl gas were obtained from the
equilibrium partial pressures of 12 mol/L hydrochloric acid
solution. The process of alkali fumigation of encrypted
information is by placing it in NH3 gas. NH3 gas were obtained
from the equilibrium partial pressures of 15 mol/L ammonia
water.
22 C. Li, K. Xiong, Y. Chen, C. Fan, Y.-L. Wang, H. Ye and M.-Q. Zhu,
ACS Appl. Mater. Interfaces, 2020, 12, 27651–27662.
23 S. Zhou, S. Guo, W. Liu, Q. Yang, H. Sun, R. Ding, Z. Qian and H.
Feng, J. Mater. Chem. C, 2020, 8, 13197–13204.
24 J. Chen, P. Zhang, G. Fang, P. Yi, F. Zeng and S. Wu, J. Phys.
Chem. B, 2012, 116, 4354–4362.
8 | J. Name., 2012, 00, 1-3
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