Organic Long Persistent Luminescence Materials in Aqueous Medium

doi:10.6023/cjoc202604002

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3688-3696.DOI: 10.6023/cjoc202604002 Previous Articles Next Articles

ARTICLE

水中分散的有机长效发光材料

种千惠^a^,^b^,^†, 王光明^b^,^†, 吴国伊^b, 闫倩倩^b, 王标兵^a^,^*(), 张卡卡^b^,^*()

^a 常州大学材料科学与工程学院江苏常州 213164
^b 中国科学院上海有机化学研究所金属有机化学全国重点实验室上海 200032

收稿日期:2026-04-01 修回日期:2026-05-27 发布日期:2026-07-14
通讯作者: 王标兵, 张卡卡
作者简介:
^† 共同第一作者.
基金资助:
国家自然科学基金(22475228); 国家自然科学基金(22175194)

Organic Long Persistent Luminescence Materials in Aqueous Medium

Qianhui Chong^a^,^b^,^†, Guangming Wang^b^,^†, Guoyi Wu^b, Qianqian Yan^b, Biaobing Wang^a^,^*(), Kaka Zhang^b^,^*()

^a School of Materials Science and Engineering, Changzhou University, Changzhou, Jiangsu 213100
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032

Received:2026-04-01 Revised:2026-05-27 Published:2026-07-14
Contact: Biaobing Wang, Kaka Zhang
About author:
Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22475228); National Natural Science Foundation of China(22175194)

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Abstract

The development of aqueous dispersions based on organic long-persistent luminescence (OLPL) materials is of great interest for biomedical applications, yet it is severely hindered by the quenching effects of moisture and oxygen. A aqueous OLPL system was successfully prepared by employing a ternary donor-sensitizer-acceptor (DSA) design. Specifically, solid-state OLPL materials exhibiting hour-long afterglow and visible-light-excitable property were constructed by integrating difluoroboron β-diketonate (BF₂bdk) as the sensitizer, N,N,N',N'-tetramethylbenzidine (TMB) as the donor, and 4-methoxy- phenyl benzoate (MeOPhB), which serves both as the acceptor and a crystalline host matrix. Taking advantage of the moderate melting point (74 ℃) of MeOPhB, these solid-state materials were efficiently converted into aqueous dispersions with the assistance of surfactants. Spectral fluorescence microscopy was utilized to verify the crystalline structure of the OLPL microparticles within the dispersion and to capture their emission spectra in situ. The resulting aqueous dispersions maintain the characteristic power-law decay of their luminescence and demonstrate remarkable stability against quenching in water. This resilience is attributed to the protective crystalline MeOPhB matrix, which effectively insulates the charge-separated states from the surrounding aqueous environment. This work not only addresses a critical gap in aqueous OLPL technology but also introduces a versatile platform for transitioning solid-state OLPL materials into water-compatible systems.

Key words: organic long persistent luminescence, room-temperature phosphorescence, difluoroboron β-diketonate, triplet excited state, thermally activated delayed fluorescence

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Qianhui Chong, Guangming Wang, Guoyi Wu, Qianqian Yan, Biaobing Wang, Kaka Zhang. Organic Long Persistent Luminescence Materials in Aqueous Medium[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3688-3696.

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Fig. & Tab. 7

Scheme 1. Synthesis process of BF2bdk, and (b) chemical structures of BF2bdk, MeOPhB, and TMB

Figure 1. (a) Photographs of BF2bdk-MeOPhB under 365 nm UV light excitation and after the light source was stopped, (b) room-temperature steady-state and delayed emission spectra (1 ms delay) of BF2bdk-MeOPhB materials, (c) room-temperature emission decay of BF2bdk-MeOPhB materials, and (d) variable-temperature delayed emission spectra (1 ms delay) of BF2bdk-MeOPhB materials excited at 365 nm

Figure 2. (a) Photographs of TMB-BF2bdk-MeOPhB under 365 nm UV light excitation and after the light source was stopped; (b) Room-temperature steady-state and delayed emission spectra (1 ms delay) of TMB-BF2bdk-MeOPhB materials excited at 365 nm; (c) OLPL spectra of TMB-BF2bdk-MeOPhB materials at different delay times; (d) Room-temperature emission decay of TMB-BF2bdk-Me- OPhB materials excited at 365 nm; (e) OLPL intensity of TMB-BF2bdk-MeOPhB materials as a function of delay time (excited at 365 nm)

Figure 3. (a) Photographs of TMB-BF2bdk-MeOPhB under 420 nm light excitation and after the light source was stopped; (b) room- temperature steady-state and delayed emission spectra (1 ms delay) of TMB-BF2bdk-MeOPhB materials excited at 420 nm; (c) OLPL spectra of TMB-BF2bdk-MeOPhB materials at different delay times; (d) room-temperature emission decay of TMB-BF2bdk-MeOPhB materials excited at 420 nm; (e) OLPL intensity of TMB-BF2bdk-MeOPhB materials as a function of delay time (excited at 420 nm)

Figure 4. Schematic illustration of the afterglow mechanism in three-component high-performance OLPL materials

Figure 5. (a) Photographs of TMB-BF2bdk-MeOPhB aqueous dispersion under 365 nm UV light excitation and after the removal of the UV light; (b) Microscope image of TMB-BF2bdk-MeOPhB aqueous dispersion; (c) Photographs of living fish injected TMB-BF2bdk- MeOPhB aqueous dispersion under 365 nm UV lamp excitation and after ceasing the light source; (d) Room-temperature steady-state and delayed emission spectra (1 ms delay) of TMB-BF2bdk-MeOPhB aqueous dispersion; (e) Delayed emission spectra of TMB-BF2bdk- MeOPhB aqueous dispersion at different delayed times after excitation with a 365 nm lamp; (f) Afterglow signal of the OLPL aqueous dispersion detected by spectroscopy fluorescence microscope system

Figure 6. (a) Photographs of TMB-BF2bdk-MeOPhB aqueous dispersion under 365 nm UV light excitation and after the removal of the UV light; (b) Microscope image of TMB-BF2bdk-MeOPhB aqueous dispersion; (c) Photographs of living fish injected TMB-BF2bdk- MeOPhB aqueous dispersion under 365 nm UV lamp excitation and after ceasing the light source; (d) Room-temperature steady-state and delayed emission spectra (1 ms delay) of TMB-BF2bdk-MeOPhB aqueous dispersion; (e) Delayed emission spectra of TMB-BF2bdk- MeOPhB aqueous dispersion at different delayed times after excitation with a 365 nm lamp; (f) Afterglow signal of the OLPL aqueous dispersion detected by spectroscopy fluorescence microscope system

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水中分散的有机长效发光材料

Organic Long Persistent Luminescence Materials in Aqueous Medium

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