Synthesis of Anthraquinone Derivate with Aggregation-Induced Emission Characteristic for Fingerprint Development

doi:10.6023/cjoc202403045

Abstract

An interesting surfactant anthraquinone derivative, named as C16-TPA-AQ, was prepared for fingerprint development by symmetrically introducing strong electron-donating triphenylaniline units. C16-TPA-AQ exhibits significant aggregation-induced emission with red fluorescence in the aggregated state, which could be used to prepare fingerprint developer with its aggregation effectively controlled by potassium chloride concentration. Such developer exerts excellent development effect on fingerprints settled on different substrates with almost no influence of background. By tuning the concentration of potassium chloride to be 0.18 mol/L, level 3 fingerprint details are successfully obtained due to micelle formation and demulsification of surfactants. Besides, the developer is also effective on aged fingerprints. This finding demonstrates the potential of red emission and surfactant aggregation induced emission luminogen (AIEgen) in latent fingerprint development.

Key words: aggregation-induced emission, anthraquinone, surfactant, fingerprint development

Cite this article

Haosen Chang, Liming Yang, Guan Wang, Xinggui Gu. Synthesis of Anthraquinone Derivate with Aggregation-Induced Emission Characteristic for Fingerprint Development[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2571-2580.

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Fig. & Tab. 9

Scheme 1. Synthetic route of C16-TPA-A

Figure 1. (A and B) UV-vis absorption spectra for C16-TPA-AQ in acetonitrile solution (c=1×10－5 mol/L) and powder, respectively; (C and D) fluorescence spectra and fluorescence lifetime of C16-TPA-AQ powder Inset shows the fluorescence image of C16-TPA-AQ powder

Figure 2. HOMO and LUMO orbitals of C16-TPA-AQ

Figure 3. (A) Fluorescence photograph, (B) fluorescence spectra, and (C) I/I0 curve of C16-TPA-AQ in acetonitrile/toluene with different toluene fraction

Figure 4. (A) Fluorescent photograph, (B) fluorescence spectra, and (C) I/I0 curve of C16-TPA-AQ in KCl solution with different concentration

Figure 5. Particle distribution of C16-TPA-AQ staining solution with different KCl concentration (A) cKCl=0 mol/L, (B) cKCl=0.09 mol/L, (C) cKCl=0.18 mol/L, (D) cKCl=0.45 mol/L

Figure 6. Fluorescence images of fingerprints on (A) glass pane, (B) plastic, (C) aluminum foil, and (D) craft knife blade substrates developed by C16-TPA-AQ, and (E) details on glass substrate (1: short ridge; 2: lake; 3: hook; 4: ridge end; 5: bifurcation)

Figure 7. (A) Photograph, (B) greyscale profile image over the yellow line, and (C) details of the fingerprint of 5-days-old fingerprint on glass substrate developed by C16-TPA-AQ

Figure 8. Fingerprint stained by C16-TPA-AQ under KCl concentration of (A) 0 mol/L, (B) 0.09 mol/L, (C) 0.18 mol/L, and their corresponding greyscale value graph (D~F); (G~I) fluorescence microscopy of fingerprint with pore details

References 46

[1]	Hazarika, P.; Russell, D. A. Angew. Chem., Int. Ed. 2012, 51, 3524.
[2]	Chen, Y.; Li, A.; Li, X.; Tu, L.; Xie, Y.; Xu, S.; Li, Z. Adv. Mater. 2023, 35, 2211917.
[3]	Zou, R.; Yu, Y.; Pan, H.; Zhang, P.; Cheng, F.; Zhang, C.; Chen, S.; Chen, J.; Zeng, R. ACS Appl. Mater. Inter. 2022, 14, 16746.
[4]	Malik, A. H.; Kalita, A.; Iyer, P. K. ACS Appl. Mater. Inter. 2017, 9, 37501.
[5]	Huang, H.; Zhou, Y.; Wang, M.; Zhang, J.; Cao, X.; Wang, S.; Cao, D.; Cui, C. Angew. Chem., Int. Ed. 2019, 58, 10132.
[6]	Suresh, R.; Thiyagarajan, S. K.; Ramamurthy, P. Sens. Actuator., B 2018, 258, 184.
[7]	Jung, H. S.; Cho, K. J.; Ryu, S. J.; Takagi, Y.; Roche, P. A.; Neuman, K. C. ACS Appl. Mater. Inter. 2020, 12, 6641.
[8]	Hansen, D. B.; Joullié, M. M. Chem. Soc. Rev. 2005, 34, 408.
[9]	Bi, X.; Shi, Y.; Peng, T.; Yue, S.; Wang, F.; Zheng, L.; Cao, Q. E. Adv. Funct. Mater. 2021, 31, 2101312.
[10]	Haque, F.; Westland, A. D.; Milligan, J.; Kerr, F. M. Forensic Sci. Int. 1989, 41, 73.
[11]	Bijl, L. J.; Theeuwen, A. B. Arch. Kriminol. 1983, 172, 93.
[12]	Keating, D. M.; Miller, J. J. J. Forensic Sci. 1993, 38, 197 pmid: 8426153
[13]	Datta, A. K. In Advances in Fingerprint Technology, Vol. 3, Eds.: Lee, H. C.; Gaensslen, R., CRC Press, Boca Raton, 2001, p. 136.
[14]	Wang, R.; Huang, Z.; Ding, L.; Yang, F.; Peng, D. ACS Appl. Nano Mater. 2022, 5, 2214.
[15]	Duan, L.; Zheng, Q.; Tu, T. Adv. Mate.. 2022, 34, 2202540.
[16]	Wang, Y. L.; Li, C.; Qu, H. Q.; Fan, C.; Zhao, P. J.; Tian, R.; Zhu, M. Q. J. Am. Chem. Soc. 2020, 142, 7497.
[17]	Chen, J.; Li, M.; Sun, R.; Xie, Y.; Reimers, J. R.; Sun, L. Adv. Funct. Mater. 2024, 2315726.
[18]	Xu, J.; Zhang, B.; Jia, L.; Fan, Y.; Chen, R.; Zhu, T.; Liu, B. ACS Appl. Mater. Inter. 2019, 11, 35294.
[19]	Ruan, N.; Qiu, Q. ;, Wei X.; Liu, J.; Wu, L.; Jia, N.; Huang, C.; James, T. D. J. Am. Chem. Soc. 2024, 146, 2072.
[20]	Lian, J.; Meng, F.; Wang, W.; Zhang, Z. Front. Chem. 2020, 8, 594864.
[21]	Li, L.; Ma, H.; Zhang, J.; Zhao, E.; Hao, J.; Huang, H.; Li, P.; Gu, X.; Tang, B.-Z. J. Am. Chem. Soc. 2021, 143, 3856.
[22]	Feng, G.; Liu, B. Acc. Chem. Res. 2018, 51, 1404.
[23]	Thomas, S. W.; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339.
[24]	Yuan, L.; Lin, W.; Yang, Y.; Chen, H. J. Am. Chem. Soc. 2012, 134, 1200. doi: 10.1021/ja209292b pmid: 22176300
[25]	Xiao, T.; Zhang, L.; Chen, D.; Zhang, Q.; Wang, Q.; Li, Z.-Y.; Sun, X.-Q. Org. Chem. Front. 2023, 10, 3245.
[26]	Seite, S.; Zucchi, H.; Moyal, D.; Tison, S.; Compan, D.; Christiaens, F.; Gueniche, A.; Fourtanier, A. Brit. J. Dermatol. 2003, 148, 291.
[27]	Hong, Y.; Lam, J. W. Y.; Tang, B.-Z. Chem. Commun. 2009, 4332.
[28]	Gui, Y.; Chen, K.; Sun, Y.; Tan, Y.; Luo, W.; Zhu, D.; Xiong, Y. Chin. J. Chem. 2022, 41, 1249.
[29]	Duan, L.; Zheng, Q.; Tu, T. Adv. Mater. 2022, 34, 2202540.
[30]	Zhou, P.; Han, K. Aggregat. 2022, 3, e160.
[31]	Zhao, Y.; Zhang, X.; Yang, Y.; Zhu, L.; Zhou, Y. Acta Chim. Sinic. 2024, 82, 265 (in Chinese).
	(赵玉强, 张霞, 杨芸如, 朱立平, 周莹, 化学学报, 2024, 82, 265.) doi: 10.6023/A23100457
[32]	Hu, J.; Jiang, W.; Yuan, L.; Duan, C.; Yuan, Q.; Long, Z.; Lou, X. Aggregat. 2021, 2, 48.
[33]	Guo, X.; Yuan, P.; Fan, J.; Qiao, X.; Yang, D.; Dai, Y.; Sun, Q.; Qin, A.; Tang, B.-Z.; Ma, D. Adv. Mater. 2021, 33, 2006953.
[34]	Zhang, Y.; Nie, F.; Zhou, L.; Wang, X.; Liu, Y.; Huo, Y.; Chen, W.; Zhao, Z. Chin. J. Org. Chem. 2023, 43, 3876 (in Chinese).
	(张越华, 聂飞, 周路, 王晓烽, 刘源, 霍延平, 陈文铖, 赵祖金, 有机化学, 2023, 43, 3876.) doi: 10.6023/cjoc202303022
[35]	Zeng, C.; Hu, P.; Wang, B.; Fang, W.; Zhao, K. Chin. J. Org. Chem. 2023, 43, 3287 (in Chinese).
	(曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, 有机化学, 2023, 43, 3287.) doi: 10.6023/cjoc202302025
[36]	Feng, L.; Li, C.; Liu, L.; Wang, Z.; Chen, Z.; Yu, J.; Ji, W.; Jiang, G.; Zhang, P.; Wang, J.; Tang, B.-Z. ACS Nan. 2022, 16, 4162.
[37]	Wu, J.; Liu, W.; Ge, J.; Zhang, H.; Wang, P. Chem. Soc. Rev. 2011, 40, 3483.
[38]	Guo, J.; Dai, J.; Peng, X.; Wang, Q.; Wang, S.; Lou, X.; Xia, F.; Zhao, Z.; Tang, B.-Z. ACS Nan. 2021, 15, 20042.
[39]	Zhang, Q.; Kuwabara, H.; Potscavage Jr, W. J.; Huang, S.; Hatae, Y.; Shibata, T.; Adachi, C. J. Am. Chem. Soc. 2014, 136, 18070.
[40]	Yang, Y.; Zhao, L.; Wang, S.; Ding, J.; Wang, L. Macromolecule. 2018, 51, 9933.
[41]	Jiang, G.; Yu, J.; Wang, J.; Tang, B.-Z. Aggregat. 2022, 3, e285.
[42]	Yu, D.; Huang, X.; Deng, M.; Lin, Y.; Jiang, L.; Huang, J.; Wang, Y. J. Phys. Chem. B 2010, 114, 14955.
[43]	Cadd, S.; Islam, M.; Manson, P.; Bleay, S. Sci. Justic. 2015, 55, 219.
[44]	Liu, Z.; Zhao, G.; Brewer, M.; Lv, Q.; Sudhölter, E. Jr. Adv. Colloid Interface Sc.. 2021, 294, 102467.
[45]	Mushtaq, M.; Al-Shalabi, E. W.; AlAmeri, W. Geoenergy Sci. Eng. 2023, 230, 212243.
[46]	Grenoble, Z.; Trabelsi, S. Adv. Colloid Interface Sci. 2018, 260, 32.

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