Piezofluorochromism in Covalent Organic Frameworks: Pressure-Induced Emission Enhancement and Blue-Shifted Emission
Jing Fang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
These authors contributed equally to this work.
Search for more papers by this authorXihan Yu
State Key Laboratory of Superhard Materials, College of Physics, Jilin University, Changchun, 130012 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Dr. Yaozu Liu
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorDr. Yusran Yusran
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorDr. Yujie Wang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorProf. Valentin Valtchev
Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, 189 Songling Road, Qingdao, 266101 P. R. China
Normandie Univ, ENSICAEN, UNICAEN, CNRS, Laboratoire Catalyse et Spectrochimie, 6 Marechal Juin, 14050 Caen, France
Search for more papers by this authorProf. Shilun Qiu
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorCorresponding Author
Prof. Bo Zou
State Key Laboratory of Superhard Materials, College of Physics, Jilin University, Changchun, 130012 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Qianrong Fang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorJing Fang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
These authors contributed equally to this work.
Search for more papers by this authorXihan Yu
State Key Laboratory of Superhard Materials, College of Physics, Jilin University, Changchun, 130012 P. R. China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Dr. Yaozu Liu
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorDr. Yusran Yusran
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorDr. Yujie Wang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorProf. Valentin Valtchev
Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, 189 Songling Road, Qingdao, 266101 P. R. China
Normandie Univ, ENSICAEN, UNICAEN, CNRS, Laboratoire Catalyse et Spectrochimie, 6 Marechal Juin, 14050 Caen, France
Search for more papers by this authorProf. Shilun Qiu
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorCorresponding Author
Prof. Bo Zou
State Key Laboratory of Superhard Materials, College of Physics, Jilin University, Changchun, 130012 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Qianrong Fang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Department of Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorAbstract
Achieving enhanced or blue-shifted emission from piezochromic materials remains a major challenge. Covalent organic frameworks (COFs) are promising candidates for the development of piezochromic materials owing to their dynamic structures and adjustable optical properties, where the emission behaviors are not solely determined by the functional groups, but are also greatly influenced by the specific geometric arrangement. Nevertheless, this area remains relatively understudied. In this study, a successful synthesis of a series of bicarbazole-based COFs with varying topologies, dimensions, and linkages was conducted, followed by an investigation of their structural and emission properties under hydrostatic pressure generated by a diamond anvil cell. Consequently, these COFs exhibited distinct piezochromic behaviors, particularly a remarkable pressure-induced emission enhancement (PIEE) phenomenon with a 16-fold increase in fluorescence intensity from three-dimensional COFs, surpassing the performance of CPMs and most organic small molecules with PIEE behavior. On the contrary, three two-dimensional COFs with flexible structures exhibited rare blue-shifted emission, whereas the variants with rigid and conjugated structures showed common red-shifted and reduced emission. Mechanism research further revealed that these different piezochromic behaviors were primarily determined by interlayer distance and interaction. This study represents the first systematic exploration of the structures and emission properties of COFs through pressure-treated engineering and provides a new perspective on the design of piezochromic materials.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
ange202409099-sup-0001-misc_information.pdf2.6 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aA. Li, S. Xu, C. Bi, Y. Geng, H. Cui, W. Xu, Mater. Chem. Front. 2021, 5, 2588–2606;
- 1bD. Zhao, M. Wang, G. Xiao, B. Zou, J. Phys. Chem. Lett. 2020, 11, 7297–7306.
- 2
- 2aY. Sagara, S. Yamane, M. Mitani, C. Weder, T. Kato, Adv. Mater. 2016, 28, 1073–1095;
- 2bZ. Ma, G. Xiao, B. Zou, Sci. Bull. 2023, 68, 1588–1590.
- 3
- 3aQ. Qi, J. Qian, X. Tan, J. Zhang, L. Wang, B. Xu, B. Zou, W. Tian, Adv. Funct. Mater. 2015, 25, 4005–4010;
- 3bL. Wang, K.-Q. Ye, H.-Y. Zhang, Chin. Chem. Lett. 2016, 27, 1367–1375;
- 3cZ. Yang, Z. Fu, H. Liu, M. Wu, N. Li, K. Wang, S.-T. Zhang, B. Zou, B. Yang, Chem. Sci. 2023.
- 4
- 4aY. Shi, Z. Ma, D. Zhao, Y. Chen, Y. Cao, K. Wang, G. Xiao, B. Zou, J. Am. Chem. Soc. 2019, 141, 6504–6508;
- 4bY. Fang, L. Zhang, Y. Yu, X. Yang, K. Wang, B. Zou, CCS Chem. 2021, 3, 2203–2210.
- 5
- 5aA. Sussardi, C. L. Hobday, R. J. Marshall, R. S. Forgan, A. C. Jones, S. A. Moggach, Angew. Chem. Int. Ed. 2020, 59, 8118–8122;
- 5bX. Guo, N. Zhu, S. P. Wang, G. Li, F. Q. Bai, Y. Li, Y. Han, B. Zou, X. B. Chen, Z. Shi, S. Feng, Angew. Chem. Int. Ed. 2020, 59, 19716–19721;
- 5cC.-X. Chen, Z.-W. Wei, Y.-N. Fan, P.-Y. Su, Y.-Y. Ai, Q.-F. Qiu, K. Wu, S.-Y. Yin, M. Pan, C.-Y. Su, Chem. 2018, 4, 2658–2669.
- 6
- 6aY. Gu, K. Wang, Y. Dai, G. Xiao, Y. Ma, Y. Qiao, B. Zou, J. Phys. Chem. Lett. 2017, 8, 4191–4196;
- 6bY. Gu, H. Liu, R. Qiu, Z. Liu, C. Wang, T. Katsura, H. Zhang, M. Wu, M. Yao, H. Zheng, K. Li, Y. Wang, K. Wang, B. Yang, Y. Ma, B. Zou, J. Phys. Chem. Lett. 2019, 10, 5557–5562;
- 6cZ. Fu, H. Liu, J. Zhao, X. Zhang, X. Zheng, B. Yang, X. Yang, K. Wang, B. Zou, J. Mater. Chem. C. 2021, 9, 14578–14582.
- 7
- 7aJ. Zou, Y. Fang, Y. Shen, Y. Xia, K. Wang, C. Zhang, Y. Zhang, Angew. Chem. Int. Ed. 2022, 61, e202207426;
- 7bC. Liu, G. Xiao, M. Yang, B. Zou, Z.-L. Zhang, D.-W. Pang, Angew. Chem. Int. Ed. 2018, 57, 1893–1897.
- 8Y. Fang, T. Shao, L. Zhang, L. Sui, G. Wu, K. Yuan, K. Wang, B. Zou, J. Am. Chem. Soc. 2021, 1, 459–466.
- 9
- 9aK. Nagura, S. Saito, H. Yusa, H. Yamawaki, H. Fujihisa, H. Sato, Y. Shimoikeda, S. Yamaguchi, J. Am. Chem. Soc. 2013, 135, 10322–10325;
- 9bS. Zhang, Y. Dai, S. Luo, Y. Gao, N. Gao, K. Wang, B. Zou, B. Yang, Y. Ma, Adv. Funct. Mater. 2017, 27, 1602276;
- 9cH. Liu, Y. Gu, Y. Dai, K. Wang, S. Zhang, G. Chen, B. Zou, B. Yang, J. Am. Chem. Soc. 2020, 142, 1153–1158.
- 10
- 10aX. Yin, C. Zhai, S. Hu, L. Yue, T. Xu, Z. Yao, Q. Li, R. Liu, M. Yao, B. Sundqvist, B. Liu, Chem. Sci. 2023, 14, 1479–1484;
- 10bX. Wang, C. Qi, Z. Fu, H. Zhang, J. Wang, H.-T. Feng, K. Wang, B. Zou, J. W. Y. Lam, B. Z. Tang, Mater. Horiz. 2021, 8, 630–638.
- 11
- 11aA. P. Cote, A. I. Benin, N. W. Ockwig, M. O′Keeffe, A. J. Matzger, O. M. Yaghi, Science. 2005, 310, 1166–1170;
- 11bH. M. El-Kaderi, J. R. Hunt, J. L. Mendoza-Cortes, A. P. Cote, R. E. Taylor, M. O′Keeffe, O. M. Yaghi, Science. 2007, 316, 268–272;
- 11cX. Guan, F. Chen, Q. Fang, S. Qiu, Chem. Soc. Rev. 2020, 49, 1357–1384;
- 11dS. Kandambeth, A. Mallick, B. Lukose, M. V. Mane, T. Heine, R. Banerjee, J. Am. Chem. Soc. 2012, 134, 19524–19527;
- 11eS. Kandambeth, K. Dey, R. Banerjee, J. Am. Chem. Soc. 2019, 141, 1807–1822;
- 11fR.-R. Liang, F.-Z. Cui, A. Ru-Han, Q.-Y. Qi, X. Zhao, CCS Chem. 2020, 2, 139–145;
- 11gM. Li, J. Liu, Y. Li, G. Xing, X. Yu, C. Peng, L. Chen, CCS Chem. 2020, 3, 696–706;
- 11hC. He, Q.-J. Wu, M.-J. Mao, Y.-H. Zou, B.-T. Liu, Y.-B. Huang, R. Cao, CCS Chem. 2020, 3, 2368–2380.
- 12
- 12aW. K. Haug, E. M. Moscarello, E. R. Wolfson, P. L. McGrier, Chem. Soc. Rev. 2020, 49, 839–864;
- 12bY. Cheng, J. Xin, L. Xiao, X. Wang, X. Zhou, D. Li, B. Gui, J. Sun, C. Wang, J. Am. Chem. Soc. 2023, 145, 18737–18741;
- 12cL. Zhang, L. Yi, Z.-J. Sun, H. Deng, Aggregate. 2021, 2, e24.
- 13Z. Fu, K. Wang, B. Zou, Chin. Chem. Lett. 2019, 30, 1883–1894.
- 14J. Fang, Z. Fu, X. Chen, Y. Liu, F. Chen, Y. Wang, H. Li, Y. Yusran, K. Wang, V. Valtchev, S. Qiu, B. Zou, Q. Fang, Angew. Chem. Int. Ed. 2023, 62, e202304234.
- 15
- 15aY. Liu, J. Li, J. Lv, Z. Wang, J. Suo, J. Ren, J. Liu, D. Liu, Y. Wang, V. Valtchev, S. Qiu, D. Zhang, Q. Fang, J. Am. Chem. Soc. 2023, 145, 9679–9685;
- 15bY. Yuan, H. Huang, L. Chen, Y. Chen, Macromolecules. 2017, 50, 4993–5003.
- 16A. F. M. El-Mahdy, M.-Y. Lai, S.-W. Kuo, J. Mater. Chem. C. 2020, 8, 9520–9528.
- 17A. F. M. El-Mahdy, A. M. Elewa, S.-W. Huang, H.-H. Chou, S.-W. Kuo, Adv. Opt. Mater. 2020, 8, 2000641.
- 18Y. Liu, J. Ren, Y. Wang, X. Zhu, X. Guan, Z. Wang, Y. Zhou, L. Zhu, S. Qiu, S. Xiao, Q. Fang, CCS Chem. 2022, 5, 2033–2045.
- 19
- 19aX. Liu, J. Li, B. Gui, G. Lin, Q. Fu, S. Yin, X. Liu, J. Sun, C. Wang, J. Am. Chem. Soc. 2021, 143, 2123–2129;
- 19bY. Chen, Z.-L. Shi, L. Wei, B. Zhou, J. Tan, H.-L. Zhou, Y.-B. Zhang, J. Am. Chem. Soc. 2019, 141, 3298–3303;
- 19cS. Seth, S. Jhulki, Mater. Horiz. 2021, 8, 700–727.
- 20H. Yuan, K. Wang, K. Yang, B. Liu, B. Zou, J. Phys. Chem. Lett. 2014, 5, 2968–2973.
- 21A. Li, F. Li, Y. Chen, Y. Xie, X. Li, X. Liu, S. Xu, W. Xu, J. Wang, Z. Li, ACS Materials Lett. 2022, 4, 2151–2158.
- 22
- 22aJ. Liu, G. Du, N. Liang, L. Yang, Y. Feng, Y. Chen, C.-J. Yao, J. Mater. Chem. C. 2023, 11, 8609–8615;
- 22bJ.-C. Yang, Z. Fu, H. Ma, T. Wang, Q. Li, K. Wang, L. Wu, P. Chen, H.-T. Feng, B. Z. Tang, ACS Materials Lett. 2023, 5, 1441–1449.
- 23X. Guan, Q. Fang, Y. Yan, S. Qiu, Acc. Chem. Res. 2022, 55, 1912–1927.
- 24J. Han, Q. Zheng, C. Jin, S. Wang, Y. Liu, Y. Zhao, J. Zhu, J. Phys. Chem. C. 2022, 126, 16859–16866.
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.