Detection of Oxygen Based on Host-Guest Doped Room-Temperature Phosphorescence Material

doi:10.6023/cjoc202404003

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2523-2529.DOI: 10.6023/cjoc202404003 Previous Articles Next Articles

ARTICLES

基于主客体掺杂室温磷光材料的氧气传感材料

张惟^a, 李庚辰^a, 苏昊^b, 戴文博^c^,^d^,^*(), 孙鹏^e, 石建兵^a, 佟斌^a, 蔡政旭^a^,^*(), 董宇平^a

a 北京理工大学材料学院结构可控先进功能材料与绿色应用实验室北京 100081
b 中国科学技术大学合肥国家实验室合肥 230088
c 温州大学化学与材料工程学院浙江温州 325035
d 温州大学温州市生物保健材料与化学重点实验室浙江温州 325035
e 北京理工大学前沿交叉科学研究院北京 100081

收稿日期:2024-04-01 修回日期:2024-05-31 发布日期:2024-07-02
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(22222501); 国家自然科学基金(22175023); 北京市自然科学基金(2232022); 北京市自然科学基金(2242060); 北京理工大学研究生科研水平和创新能力提升计划(2023YCXZ016)

Detection of Oxygen Based on Host-Guest Doped Room-Temperature Phosphorescence Material

Wei Zhang^a, Gengchen Li^a, Hao Su^b, Wenbo Dai^c^,^d(), Peng Sun^e, Jianbing Shi^a, Bin Tong^a, Zhengxu Cai^a(), Yuping Dong^a

a Beijing Key Laboratory of Construction Tailorable Advanced Functional Materials and Green Applications, School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081
b Hefei National Laboratory, University of Science and Technology of China, Hefei 230088
c College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
d Key Lab of Biohealth Materials and Chemistry of Wenzhou, Wenzhou University, Wenzhou, Zhejiang 325035
e Advanced Research Institute of Multidisciplinary Sciences, Beijing Institute of Technology, Beijing 100081

Received:2024-04-01 Revised:2024-05-31 Published:2024-07-02
Contact: *E-mail: wbdai@wzu.edu.cn; caizx@bit.edu.cn
About author:
† The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22222501); National Natural Science Foundation of China(22175023); Natural Science Foundation of Beijing(2232022); Natural Science Foundation of Beijing(2242060); Beijing Institute of Technology Research and Innovation Promoting Project(2023YCXZ016)

1. .pdf(2010KB)

Abstract

Quantitative oxygen detection, especially at low concentrations, holds significant importance in the realms of biology, complex environments, and chemical process engineering. Due to the high sensitivity and rapid response of the triplet excitons of phosphorescence to oxygen, pure organic room-temperature phosphorescence (RTP) materials have garnered widespread attention in recent years for oxygen detection. However, simultaneously achieving ultralong phosphorescence at room temperature and quantitative oxygen detection from pure organic host-guest doped materials poses challenges. The densely packed materials may decrease non-radiative decay to increase the phosphorescence, but are unsuitable for oxygen diffusion in oxygen detection. Herein, the oxygen sensitivity of host-guest doped RTP materials using 4-bromo-N,N-bis(4-(tert- butyl)phenyl)aniline (TPABuBr) as the host and 6-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (NIBr) as the guest was developed. The doped material exhibits fluorescence-phosphorescence dual-emission behavior at room temperature. The tert-butyl groups in TPABuBr facilitate appropriate intermolecular spacing in the crystal state, enhancing oxygen permeability. Therefore, oxygen penetration can quench the phosphorescence emission. The observed linear relationship between the phosphorescence intensity of the doped material and the oxygen volume fraction conforms to the Stern-Volmer equation, suggesting its potential for quantitative analysis of oxygen concentration. The calculated limit of detection is 0.015% (φ), enabling the analysis of oxygen with a volume fraction of less than 2.5% (φ). Moreover, the doped materials demonstrate rapid response and excellent photostability, indicating their potential utility as oxygen sensors. This study elucidates the design and characteristics of NIBr/TPABuBr doped materials, highlighting their potential application in oxygen concentration detection and offering insights for the design of oxygen sensors.

Key words: organic room-temperature phosphorescence, host-guest doped strategy, oxygen sensitive materials, oxygen concentration detection

Cite this article

Wei Zhang, Gengchen Li, Hao Su, Wenbo Dai, Peng Sun, Jianbing Shi, Bin Tong, Zhengxu Cai, Yuping Dong. Detection of Oxygen Based on Host-Guest Doped Room-Temperature Phosphorescence Material[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2523-2529.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

Scheme 1. Chemical structures and design strategy of organic host matrix and guest molecules for oxygen sensing

Figure 1. (a) Normalized UV-vis absorption (Abs.) and steady-state PL spectra of guest NIBr in THF solution (concentration: 1×10－5 mol/L), (b) steady-state PL and delayed (delayed time: 50 μs) emission spectra of NIBr/TPABuBr doped materials (mass ratio: host∶guest=100∶1), (c) phosphorescence decay curve of NIBr/TPABuBr, and (d) PL spectra of NIBr/TPABuBr in air and vacuum (insets: photographs of the NIBr/TPABuBr in air and vacuum under 365 nm UV light)

Figure 2. (a) Molecular stacking and intermolecular interactions in TPABuBr crystal, (b) illustration of oxygen diffusion in NIBr/ TPABuBr, (c) reversible phosphorescence on-off cycles under alternating exposure to air/vacuum for NIBr/TPABuBr, and (d) enlargement of the response transient curves of NIBr/TPABuBr doped materials with air

Figure 3. (a) Normalized delayed spectra with the increase of oxygen fraction, and (b) plot of I0/I－1 against oxygen fraction

References 17

[1]	O’Riordan, T. C.; Voraberger, H.; Kerry, J. P.; Papkovsky, D. B. Anal. Chim. Act. 2005, 530, 135.
[2]	(a) Wu, C.; Bull, B.; Christensen, K.; McNeill, J. Angew. Chem., Int. Ed. 2009, 48, 2741.
	(b) Wang, S.; Gu, K.; Guo, Z.; Yan, C.; Yang, T.; Chen, Z.; Tian, H.; Zhu, W.-H. Adv. Mater. 2019, 31, 1805735.
	(c) Feng, G.; Zhang, G.-Q.; Ding, D. Chem. Soc. Rev. 2020, 49, 8179.
	(d) Zhang, G.; Palmer, G. M.; Dewhirst, M. W.; Fraser, C. L. Nat. Mater. 2009, 8, 747.
	(e) Godet, I.; Doctorman, S.; Wu, F.; Gilkes, D. M. Cell. 2022, 11, 686.
[3]	Seife, C. Scienc. 2003, 299, 1971.
[4]	(a) Jin, H.; Jiang, X.; Sun, Z.; Gui, R. Coord. Chem. Rev. 2021, 431, 213694.
	(b) Ju, Y.; Wu, X. g.; Huang, S.; Dai, G.; Song, T.; Zhong, H. Adv. Funct. Mater. 2021, 32, 2108296.
	(c) Liu, H.; Pan, G.; Yang, Z.; Wen, Y.; Zhang, X.; Zhang, S. T.; Li, W.; Yang, B. Adv. Opt. Mater. 2022, 10, 2102814.
[5]	(a) Liu, X. Q.; Zhang, K.; Gao, J. F.; Chen, Y. Z.; Tung, C. H.; Wu, L. Z. Angew. Chem., Int. Ed. 2020, 59, 23456.
	(b) Zeng, Y.; Nguyen, V. P.; Li, Y.; Kang, D. H.; Paulus, Y. M.; Kim, J. ACS Appl. Mater. Interface. 2022, 14, 18182.
	(c) Kou, M.; Qin, F.; Wang, Y.; Zhang, X.; Hu, Z.; Zhao, H.; Zhang, Z. J. Phys. Chem. Lett. 2023, 14, 7193.
[6]	(a) Dai, W.; Bianconi, T.; Ferraguzzi, E.; Wu, X.; Lei, Y.; Shi, J.; Tong, B.; Carlotti, B.; Cai, Z.; Dong, Y. ACS Mater. Lett. 2021, 3, 1767.
	(b) Cao, Y.; Wang, D.; Zhang, Y.; Li, G.; Gao, C.; Li, W.; Chen, X.; Chen, X.; Sun, P.; Dong, Y.; Cai, Z.; He, Z. Angew. Chem., Int. Ed. 2024, e202401331.
	(c) Zhang, Y.; Zhang, W.; Xia, J.; Xiong, C.; Li, G.; Li, X.; Sun, P.; Shi, J.; Tong, B.; Cai, Z.; Dong, Y. Angew. Chem., Int. Ed. 2023, 62, e202314273.
	(d) Zhao, Y.; Yang, J.; Liang, C.; Wang, Z.; Zhang, Y.; Li, G.; Qu, J.; Wang, X.; Zhang, Y.; Sun, P.; Shi, J.; Tong, B.; Xie, H.-Y.; Cai, Z.; Dong, Y. Angew. Chem., Int. Ed. 2024, 63, e202317431.
	(e) Dai, W.; Jiang, Y.; Lei, Y.; Huang, X.; Sun, P.; Shi, J.; Tong, B.; Yan, D.; Cai, Z.; Dong, Y. Chem. Sci. 2024, 15, 4222.
[7]	He, T.; Guo, W. J.; Chen, Y. Z.; Yang, X. F.; Tung, C. H.; Wu, L. Z. Aggregat. 2023, 4, e250.
[8]	(a) Han, X.; Chen, K.; Lei, Y.; Huang, J.; Wei, S.; Cai, Z.; Wu, H.-Y.; Liu, M.-C.; Huang, X.-B.; Dong, Y. ACS Mater. Lett. 2022, 4, 1764.
	(b) Dai, W.; Li, G.; Zhang, Y.; Ren, Y.; Lei, Y.; Shi, J.; Tong, B.; Cai, Z.; Dong, Y. Adv. Funct. Mater. 2023, 33, 2210102.
	(c) Dai, W.; Niu, X.; Wu, X.; Ren, Y.; Zhang, Y.; Li, G.; Su, H.; Lei, Y.; Xiao, J.; Shi, J.; Tong, B.; Cai, Z.; Dong, Y. Angew. Chem., Int. Ed. 2022, 61, e202200236.
	(d) Lei, Y.; Dai, W.; Guan, J.; Guo, S.; Ren, F.; Zhou, Y.; Shi, J.; Tong, B.; Cai, Z.; Zheng, J.; Dong, Y. Angew. Chem., Int. Ed. 2020, 59, 16054.
	(e) Dai, W.; Zhang, Y.; Wu, X.; Guo, S.; Ma, J.; Shi, J.; Tong, B.; Cai, Z.; Xie, H.; Dong, Y. CCS Chem. 2022, 4, 2550.
	(f) Ding, B.; Ma, L.; Huang, Z.; Ma, X.; Tian, H. Sci. Adv. 2021, 7, eabf9668.
	(g) Song, J.; Ma, X. Chin. J. Org. Chem. 2021, 41, 4519 (in Chinese).
	(宋金明, 马骧, 有机化学, 2021, 41, 4519.) doi: 10.6023/cjoc202100082
	(h) Han, P.; Qin, A. Chin. J. Org. Chem. 2023, 43, 2254 (in Chinese).
	(韩鹏博, 秦安军, 有机化学, 2023, 43, 2254.) doi: 10.6023/cjoc202300032
[9]	(a) Lei, Y.; Yang, J.; Dai, W.; Lan, Y.; Yang, J.; Zheng, X.; Shi, J.; Tong, B.; Cai, Z.; Dong, Y. Chem. Sci. 2021, 12, 6518.
	(b) Li, G.; Dai, W.; Lei, Y.; Shi, J.; Tong, B.; Cai, Z.; Dong, Y. ChemPhotoChe. 2022, 7, e202200198.
	(c) Guo, Y.; Chen, K.; Hu, Z.; Lei, Y.; Liu, X.; Liu, M.; Cai, Z.; Xiao, J.; Wu, H.; Huang, X. J. Phys. Chem. Lett. 2022, 13, 7607.
	(d) Lei, Y.; Dai, W.; Li, G.; Zhang, Y.; Huang, X.; Cai, Z.; Dong, Y. J. Phys. Chem. Lett. 2023, 14, 1794.
	(e) Ren, Y.; Dai, W.; Guo, S.; Dong, L.; Huang, S.; Shi, J.; Tong, B.; Hao, N.; Li, L.; Cai, Z.; Dong, Y. J. Am. Chem. Soc. 2022, 144, 1361.
	(f) Xiao, F.; Gao, H.; Lei, Y.; Dai, W.; Liu, M.; Zheng, X.; Cai, Z.; Huang, X.; Wu, H.; Ding, D. Nat. Commun. 2022, 13, 186.
	(g) Zhang, Y.; Xiong, C.; Wang, W.; Dai, W.; Ren, Y.; Xia, J.; Li, G.; Shi, J.; Tong, B.; Zheng, X.; Shao, X.; Cai, Z.; Dong, Y. Aggregat. 2023, 4, e310.
[10]	Guo, S.; Dai, W.; Chen, X.; Lei, Y.; Shi, J.; Tong, B.; Cai, Z.; Dong, Y. ACS Mater. Lett. 2021, 3, 379.
[11]	Gu, F.; Jiang, T.; Ma, X. ACS Appl. Mater. Interface. 2021, 13, 43473.
[12]	Zhou, Y.; Qin, W.; Du, C.; Gao, H.; Zhu, F.; Liang, G. Angew. Chem., Int. Ed. 2019, 58, 12102.
[13]	Guo, W.-J.; Chen, Y.-Z.; Tung, C.-H.; Wu, L.-Z. CCS Chem. 2021, 3, 1384.
[14]	(a) Cai, Y.; Guo, Z.; Chen, J.; Li, W.; Zhong, L.; Gao, Y.; Jiang, L.; Chi, L.; Tian, H.; Zhu, W.-H. J. Am. Chem. Soc. 2016, 138, 2219.
	(b) Lumpi, D.; Holzer, B.; Bintinger, J.; Horkel, E.; Waid, S.; Wanzenböck, H. D.; Marchetti-Deschmann, M.; Hametner, C.; Bertagnolli, E.; Kymissis, I.; Fröhlich, J. New J. Chem. 2015, 39, 1840.
[15]	Chen, X.; Xu, C.; Wang, T.; Zhou, C.; Du, J.; Wang, Z.; Xu, H.; Xie, T.; Bi, G.; Jiang, J.; Zhang, X.; Demas, J. N.; Trindle, C. O.; Luo, Y.; Zhang, G. Angew. Chem., Int. Ed. 2016, 55, 9872.
[16]	(a) Wang, Y.; Yang, J.; Gong, Y.; Fang, M.; Li, Z.; Tang, B. Z. SmartMa. 2020, 1, 1006.
	(b) Xu, Z.; He, Y.; Shi, H.; An, Z. SmartMa. 2023, 4, e1139.
	(c) Cai, S.; Yao, X.; Ma, H.; Shi, H.; An, Z. Aggregat. 2023, 4, e320.
	(d) Zhang, Y.; Li, J.; Zhao, J.; Li, X.; Wang, Z.; Huang, Y.; Zhang, H.; Liu, Q.; Lei, Y.; Ding, D. Angew. Chem., Int. Ed. 2024, 63, e202313890.
[17]	(a) Huang, R. W.; Wei, Y. S.; Dong, X. Y.; Wu, X. H.; Du, C. X.; Zang, S. Q.; Mak, T. C. W. Nat. Chem. 2017, 9, 689.
	(b) Xie, Z.; Ma, L.; deKrafft, K. E.; Jin, A.; Lin, W. J. Am. Chem. Soc. 2010, 132, 922.
	(c) Wang, X.-D.; Wolfbeis, O. S. Chem. Soc. Rev. 2014, 43, 3666.

基于主客体掺杂室温磷光材料的氧气传感材料

Detection of Oxygen Based on Host-Guest Doped Room-Temperature Phosphorescence Material

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 4

References 17

Related Articles 0

Recommended Articles

Metrics

Comments