Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound

doi:10.6023/cjoc202211030

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1824-1831.DOI: 10.6023/cjoc202211030 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑；有机硼化学专辑

ARTICLES

一种三苯胺基二氟硼发光化合物的力致可逆荧光变色及数据安全保护研究

徐茂财^a, 田佳壮^a, 杨艳华^a^,^*(), 苟高章^b^,^*(), 李福敏^c, 邵林^d^,^*(), 池可心^e

a 昆明学院化学化工学院云南省金属有机分子材料与器件重点实验室昆明 650214
b 红河学院化学与资源工程学院云南省天然药物与化学生物学重点实验室云南蒙自 661100
c 大理州食品检验检测院理化检验中心云南大理 671100
d 大理州食品检验检测院色谱分析中心云南大理 671100
e 上海爱博才思分析仪器贸易有限公司上海 200335

收稿日期:2022-11-25 修回日期:2023-02-01 发布日期:2023-03-17
通讯作者: 杨艳华, 苟高章, 邵林
作者简介:
† 共同第一作者
基金资助:
云南省大学生创新创业计划训练(202111393026); 云南省科技厅基础研究(202101AU070060); 昆明学院人才引进计划(YJL2008); 云南省一流本科专业建设专项资助项目

Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound

Maocai Xu^a, Jiazhuang Tian^a, Yanhua Yang^a(), Gaozhang Gou^b(), Fumin Li^c, Lin Shao^d(), Kexin Chi^e

a Yunnan Key Laboratory of Metal-Organic Molecular Materials and Device, School of Chemistry and Chemical Engineering, Kunming University, Kunming 650214
b Key Laboratory of Natural Pharmaceutical & Chemical Biology of Yunnan Province, School of Chemistry and Resources Engineering, Honghe University, Mengzi, Yunnan 661100
c Physical and Chemical Inspection Center, Dali Institute for Food Control, Dali, Yunnan 671100
d Chromatographic Analysis Center, Dali Institute for Food Control, Dali, Yunnan 671100
e Shanghai AB SCIEX Analytical Instrument Trading Co., Shanghai 200335

Received:2022-11-25 Revised:2023-02-01 Published:2023-03-17
Contact: Yanhua Yang, Gaozhang Gou, Lin Shao
About author:
† These authors contributed equally to this work.
Supported by:
Innovation and Entrepreneurship Training Program for University Students in Yunnan Province(202111393026); Basic Research Programs of Yunnan Science and Technology Department(202101AU070060); Research Foundation for Introduced Talents of Kunming University(YJL2008); First-rate Undergraduate Major Construction Project of Chemistry in Yunnan Province

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Abstract

In order to meet the demand of data storage security in the rapid development of information, a π-conjugated triphenylamine-based difluororboron compound (PyTPABF₂) was designed and successfully synthesized. PyTPABF₂ held positive solvatochromism behavior, intramolecular charge transfer property, aggregation-induced emission behavior and high contrast mechanofluorochromic performance. The as-prepared powders PyTPABF₂ exhibited bright green fluorescence (533 nm), which luminescent color switching to khaki (556 nm) under external mechanical stimulation, meanwhile, the color could recover to original state after fuming. The X-ray diffraction (XRD) measurement demonstrated that this phenomenon originated from the process of phase transformation between crystalline and amorphous. More importantly, PyTPABF₂-based data secu-rity paper could be achieved rewritable storage of information. It was of assistance in the rational design of smart luminescent materials.

Key words: triphenylamine-based difluororboron compound, mechanofluorochromic behavior, data security protection

Cite this article

Maocai Xu, Jiazhuang Tian, Yanhua Yang, Gaozhang Gou, Fumin Li, Lin Shao, Kexin Chi. Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1824-1831.

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Fig. & Tab. 9

Scheme 1. Synthetic route of PyTPABF2

Figure 1. Overlay plots of 1H NMR spectra

Figure 2. (a) UV-vis absorption spectra and (b) normalized fluorescence emission spectra of PyTPABF2 in different solvents Inset: photos in different solvents irradiation 365 nm

Frontier orbital	Ground state		Excited state
Frontier orbital	Electron density distribution	Energy level	Electron density distribution	Energy level
LUMO+1		–0.94 eV		–1.07 eV
LUMO		–1.66 eV		–2.05 eV
HOMO		–6.78 eV		–6.72 eV
HOMO–1		–7.09 eV		–7.07 eV

Table 1. Calculated spatial distributions and optimized conformation of PyTPABF2 in ground and excited states

	Ground state	Excited state
Optimized conformation

Table 2. Caclulated optimized conformation of PyTPABF2 in ground and excited states

Transition	Hole	Transition probability	Particle
S₀→S₁
S₀←S₁

Table 3. Natural transition orbitals (NTO) for S0→S1 and S1→S0 transitions of PyTPABF2 in CH3CN

Figure 3. (a) Emission spectra of PyTPABF2 in THF/water mixtures with different water fractions (20%<fw<85%), and (b) plots of emission peak intensity versus fw in THF/water mixtures Inset: photos in fw irradiation 365 nm

Figure 4. (a) Normalized fluorescence emission spectra (λex=365 nm) and (b) XRD patterns of PyTPABF2 in different solid states Inset: photos in different solid states irradiation 365 nm

Figure 5. Photos of the luminescence rewriting process on the PyTPABF2-loaded security paper under 365 nm irradiation

References 21

[1]	Li, Z.; Chen, H.; Li, B.; Xie, Y.; Gong, X.; Liu, X.; Li, H.; Zhao, Y. Adv. Sci. 2019, 21, 1901529.
[2]	Wu, Z.; Du, B.; Tong, G.; Zhang, H.; Zhang, Y.; Xia, J.; Zhao, Z. Chem. Eng. J. 2022, 428, 131016. doi: 10.1016/j.cej.2021.131016
[3]	Lu, L.; Wang, K.; Wu, H.; Qin, A.; Tang, B. Z. Chem. Sci. 2021, 12, 7058. doi: 10.1039/D1SC00722J
[4]	Yan, N.; Zhang, W.; Li, G.; Zhang, S.; Yang, X.; Zhou, K.; Pei, D.; Zhao, Z.; He, G. Mater. Chem. Front. 2021, 5, 4128. doi: 10.1039/D1QM00327E
[5]	Ma, Y.; Zhang, Y.; Kong, L.; Yang, J. Molecules 2018, 12, 3255.
[6]	Hu, J.; Wang, J.; Liu, R.; Li, Y.; Lu, J.; Zhu, H. Dyes Pigm. 2018, 153, 84. doi: 10.1016/j.dyepig.2018.02.007
[7]	Fu, S.; Feng, X.; Zhou, N.; Zhang, S.; Liu, X.; Xu, D. J. Lumin. 2022, 247, 118802. doi: 10.1016/j.jlumin.2022.118802
[8]	Pannipara, M.; Al-Sehemi, A. D.; Kalam, A.; Asiri, A. M. Opt. Mater. 2017, 72, 442. doi: 10.1016/j.optmat.2017.06.037
[9]	Song, Z.; Liu, R.; Li, Y.; Shi, H.; Hu, J.; Cai, X.; Zhu, H. J. Mater. Chem. C 2016, 4, 2553. doi: 10.1039/C6TC00237D
[10]	Zhang, H.; Chen, P.-Z.; Niu, L.-Y.; Yang, Q.-Z. Mater. Chem. Front. 2020, 4, 285. doi: 10.1039/C9QM00672A
[11]	Saotome, S.; Suenaga, K.; Tanaka, K.; Chujo, Y. Mater. Chem. Front. 2020, 4, 1781. doi: 10.1039/C9QM00719A
[12]	Nandi, R. P.; Sudhakar, P.; Kalluvettukuzhy, N. K.; Thilagar, P. Chem.-Eur. J. 2020, 69, 16306.
[13]	Sun, J.; Yang, H.; Simalou, O.; Lv, K.; Zhai, L.; Zhao, J.; Lu, R. New J. Chem. 2019, 43, 10134. doi: 10.1039/C9NJ02410G
[14]	Li, P.; Liang, Q.; Hong, E. Y.-H.; Chan, C.-Y.; Cheng, Y.-H.; Leung, M.-Y.; Chan, M.-Y.; Low, K.-H.; Wu, H.; Yam, V. W.-W. Chem. Sci. 2020, 42, 11601.
[15]	Kuno, A.; Tohnai, N.; Yasuda, N.; Maeda, H. Chem.-Eur. J. 2017, 47, 11357.
[16]	Kubota, Y.; Niwa, T.; Jin, J.; Funabiki, K.; Matsui, M. Org. Lett. 2015, 12, 3174.
[17]	Kubota, Y.; Sakuma, Y.; Funabiki, K.; Matsui, M. J. Phys. Chem. A 2014, 38, 8717.
[18]	Michalsky, I.; Gensch, V.; Walla, C.; Hoffmann, M.; Rominger, F.; Oeser, T.; Tegder, P.; Dreuw, A.; Kivala, M. Chem.-Eur. J. 2022, 34, e202200326.
[19]	Tu, J.; Fan, Y.; Wang, J.; Li, X.; Liu, F.; Han, M.; Wang, C.; Li, Q.; Li, Z. J. Mater. Chem. C 2019, 39, 12256.
[20]	Aleveque, O.; Achelle, S.; Sanguient, L. ChemPhotoChem 2023, 7, e202200201.
[21]	Hu, R.; Lager, E.; Aguilar-Aguilar, A.; Liu, J.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Zhong, Y.; Wong, K. S.; Pena-Cabrera, E.; Tang, B. Z. J. Phys. Chem. C 2009, 36, 15845.

一种三苯胺基二氟硼发光化合物的力致可逆荧光变色及数据安全保护研究

Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound

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