Aggregation-Induced Emission (AIE) Active Fluoroboronated Pyridylhydrazinyl Aldehyde Hydrozone Dyes: Synthesis, Crystal Structure and Optical Properties

doi:10.6023/cjoc202403032

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2545-2553.DOI: 10.6023/cjoc202403032 Previous Articles Next Articles

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聚集诱导发光活性氟硼吡啶肼醛腙燃料的合成、晶体结构及光学性质

宫清宝^a, 吕翔^b, 于长江^b^,^*(), 李婉婉^b, 赵全胜^b^,^*(), 焦莉娟^b, 郝二红^b^,^*()

a 皖南医学院脑科学研究院皖南医学院第一附属医院/弋矶山医院神经外科安徽芜湖 241001
b 安徽师范大学化学与材料科学学院功能分子固体教育部重点实验室安徽芜湖 241002

收稿日期:2024-03-22 修回日期:2024-05-11 发布日期:2024-06-13
基金资助:
国家自然科学基金(22271002); 安徽省自然科学基金(2008085QB67); 安徽省自然科学基金(2308085J14); 安徽省高等学校科学研究项目(2023AH050149); 安徽省高等学校科学研究项目(KJ2021A0126); 安徽省教育厅高校优秀科研创新团队(2022AH010073)

Aggregation-Induced Emission (AIE) Active Fluoroboronated Pyridylhydrazinyl Aldehyde Hydrozone Dyes: Synthesis, Crystal Structure and Optical Properties

Qingbao Gong^a, Xiang Lü^b, Changjiang Yu^b(), Wanwan Li^b, Quansheng Zhao^b(), Lijuan Jiao^b, Erhong Hao^b()

a Department of Neurosurgery, The First Affiliated Hospital/Yijishan Hospital of Wannan Medical College, Institutes of Brain Science, Wannan Medical College, Wuhu, Anhui 241001
b Key Laboratory of Functional Molecular Solids, Ministry of Education; School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002

Received:2024-03-22 Revised:2024-05-11 Published:2024-06-13
Contact: *E-mail: yuchj@ahnu.edu.cn; zqs2012@ahnu.edu.cn; haoehong@ahnu.edu.cn
Supported by:
National Natural Science Foundation of China(22271002); Anhui Provincial Natural Science Foundation(2008085QB67); Anhui Provincial Natural Science Foundation(2308085J14); Scientific Research Project of Anhui Provincial Colleges and Universities(2023AH050149); Scientific Research Project of Anhui Provincial Colleges and Universities(KJ2021A0126); Excellent Scientific Research and Innovation Team in Natural Sciences of Anhui Provincial Department of Education(2022AH010073)

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Abstract

A new family of fluoroboronated pyridylhydrazinyl aldehyde hydrozone fluorophores named BOPAHs were developed via a simple one-pot two-step reaction from chloro-2-hydrazinylpyridine and aromatic aldehyde derivatives. They were well characterized by NMR, HRMS, and X-ray crystal structures. They exhibit main absorption from 400 nm to 600 nm and emission bands from 500 nm to 700 nm. The absorption/emission bands redshift with increased polarity of solvents indicate a distinct intramolecular charge transfer characteristic, further confirmed by density functional theory (DFT) calculations. These BOPAHs display weak fluorescence in solutions, but they exhibit obvious aggregation-induced emission properties, possibly resulting from weak intermolecular interactions by fixing the molecular conformations in aggregate states.

Key words: aggregation-induced emission, organoboron dyes, organic synthesis, optical properties

Cite this article

Qingbao Gong, Xiang Lü, Changjiang Yu, Wanwan Li, Quansheng Zhao, Lijuan Jiao, Erhong Hao. Aggregation-Induced Emission (AIE) Active Fluoroboronated Pyridylhydrazinyl Aldehyde Hydrozone Dyes: Synthesis, Crystal Structure and Optical Properties[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2545-2553.

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Fig. & Tab. 8

Figure 1. Chemical structures of AIE-active PPBs and BOA- HYs and our designed BOPAHs based on BF2-anchored hydrozones

Scheme 1. Syntheses and yields of BOAHYs 1a~1g

Figure 2. X-ray crystal structures and packing diagrams of (a) 1b; (b) 1d; (c) 1e; (d) 1f

Figure 3. Normalized absorption (a) and emission (b) spectra of BOPAHs 1a and 1d~1g in dichloromethane; absorption (c) and emission (d) spectra of 1g in different organic solvents

Dye	Dichloromethane					Solid powder
Dye	λ_abs^max/nm	λ_em^max/nm	ε^b	Stokes-shift/cm^－1	ϕ^c	λ_em/nm (ϕ^d)
1a	472	552	32400	3100	0.02	578 (0.10)
1b	492	533	49000	1700	0.02	609 (0.10)
1c	469	560	36300	3500	0.06	566 (0.12)
1d	495	535	44700	1500	0.01	625 (0.05)
1e	515	613	42700	3100	0.01	750 (0.02)
1f	499	556	47900	2100	0.01	608 (0.05)
1g	488	605	46800	4000	0.02	617 (0.06)

Table 1. Photophysical data of 1a~1g in dichloromethane and solid powder states at room temperaturea

Figure 4. (a) Z/E photoisomerization process monitored via 1H NMR spectroscopy, starting from the pure Z isomer of 1a (0 min, upper spectra) in CDCl3 (20 mmol/L) irradiated by a 50 W LED lamp for 60 min (lower spectra), and absorption (b) and emission (c) spectra of (Z)-1a (10 μmol/L) before photoirradiation and upon irradiation with a 50 W LED lamp for 5 min in dichloromethane

Figure 5. Molecular orbital amplitude plots of the HOMOs and LUMOs of 1f and 1g

Figure 6. Relative fluorescence spectra of 1a (a), 1b (b), 1d (c) and 1g (d) in acetonitrile/water with different water fractions (fw)

References 35

[1]	Chen, H.; Han, P.; Qin, A.; Tang, B. Z. Acta Chim. Sinic. 2023, 81, 1420 (in Chinese).
	(徐赫, 韩鹏博, 秦安军, 唐本忠, 化学学报, 2023, 81, 1420.)
[2]	Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. doi: 10.1021/acs.chemrev.5b00263 pmid: 26492387
[3]	Zhu, F.-Y.; Mei, L.-J.; Tian, R.; Li, C.; Xiang, S.-L.; Zhu, M.-Q.; Wang, Y.-L.; Tang, B. Z. Chem. Soc. Rev. 2024, 53, 3350.
[4]	Chen, M.; Dong, R.; Song, J.; Qi, J.; Zhang, J.; Zhao, Z.; Zhang, W.; Li, Y.; Tang, B. Z. Adv. Healthcare Mate.. 2024, 13, 2303967.
[5]	Yang, L.-L.; Wang, H.; Zhang, J.; Wu, B.; Li, Q.; Chen, J.-Y.; Tang, A.-L.; Lam, J. W. Y.; Zhao, Z.; Yang, S.; Tang, B. Z. Nat. Commun. 2024, 15, 999.
[6]	Chen, Y.-J.; Pu, M.-Q.; Wu, L.-T.; Sun, X.-L.; Wan, W.-M. Chin. J. Chem. 2023, 41, 1705.
[7]	Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 18, 1740.
[8]	Zhao, Y.; Chen, P.; Li, G.; Niu, Z.; Wang, E. Chin. J. Org. Che.. 2023, 43, 2156 (in Chinese).
	(赵洋, 陈盼盼, 李高楠, 钮智刚, 王恩举, 有机化学, 2023, 43, 2156.)
[9]	Gui, Y.; Chen, K.; Sun, Y.; Tan, Y.; Luo, W.; Zhu, D.; Xiong, Y.; Yan, D.; Wang, D.; Tang, B. Z. Chin. J. Chem. 2023, 41, 1249.
[10]	Long, R.; Tang, C.; Xu, J.; Li, T.; Tong, C.; Guo, Y.; Shi, S.; Wang, D. Chem. Commun. 2019, 55, 10912.
[11]	Kim, D.; Lee, U.; Bouffard, J. Kim, Y. Adv. Opt. Mater. 2020, 8, 1902161.
[12]	Han, G.; Kim, D.; Park, Y.; Bouffard, J.; Kim, Y. Angew. Che.. 2015, 127, 3984.
[13]	Marsh, A. V.; Cheetham, N. J.; Little, M.; Dyson, M.; White, A. J.; Beavis, P.; Warriner, C. N.; Swain, A. C.; Stavrinou, P. N.; Heeney, M. Angew. Che.. 2018, 130, 10800.
[14]	Zeng, C.; Hu, P.; Wang, B.; Fang, W.; Zhao, K. Chin. J. Org. Che.. 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.)
[15]	Huang, W.; Zhao, X.; Zhang, S.; Ying, L.; Miao, X.; Deng, W. Dyes Pig.. 2024, 225, 112063.
[16]	Bismillah, A. N.; Aprahamian, I. Chem. Soc. Re.. 2021, 50, 5631.
[17]	Mao, Z.; Kim, J. H.; Lee, J.; Xiong, H.; Zhang, F.; Kim, J. S. Coord. Chem. Re.. 2023, 476, 214908.
[18]	Chen, Z.; Ni, Z.; Chen, X.-Y.; Xu, Y.; Yu, C.; Wang, S.; Wang, X.-Y.; Lu, H. Aggregat. 2024, 5, e498.
[19]	Ji, C.; Yang, J.; Hu, S.; Mack, J.; Zhang, Y.; Lu, H.; Gai, L. Dyes Pig.. 2023, 220, 111707.
[20]	Qian, H.; Cousins, M. E.; Horak, E. H.; Wakefield, A.; Liptak, M. D.; Aprahamian, I. Nat. Chem. 2017, 9, 83. doi: 10.1038/nchem.2612 pmid: 27995926
[21]	Murali, A. C.; Nayak, P.; Panda, R.; Das, R.; Venkatasubbaiah, K. ACS Appl. Opt. Mate.. 2023, 1, 1033.
[22]	Tanaka, K.; Gon, M.; Ito, S.; Ochi, J.; Chujo, Y. Coord. Chem. Re.. 2022, 472, 214779.
[23]	Nakamura, M.; Kanetani, I.; Gon, M.; Tanaka, K. Angew. Chem., Int. Ed. 2024, e202404178.
[24]	Duan, W.; Liu, Q.; Huo, Y.; Cui, J.; Gong, S.; Liu, Z. Org. Biomol. Chem. 2018, 16, 4977.
[25]	Yordanov, D.; Smolka, R.; Nakashima, K.; Hirashima, S. I.; Matsushima, Y.; Vala, M.; Krajcovic, J.; Weiter, M.; Miura, T.; Georgiev, A. J. Org. Che.. 2023, 88, 17206.
[26]	Wang, X.; Wu, Y.; Liu, Q.; Li, Z.; Yan, H.; Ji, C.; Duan, J.; Liu, Z. Chem. Commu.. 2015, 51, 784.
[27]	Wang, X.; Liu, Q.; Yan, H.; Liu, Z.; Yao, M.; Zhang, Q.; Gong, S.; He, W. Chem. Commun. 2015, 51, 7497.
[28]	Liu, Q.; Wang, X.; Yan, H.; Wu, Y.; Li, Z.; Gong, S.; Liu, P.; Liu, Z. J. Mater. Chem. C 2015, 3, 2953.
[29]	Wang, H.; Zhang, C.; Jiang, Z.; Xu, L.; Liu, Z. Dalton. Trans. 2023, 52, 1393.
[30]	Ni, J.-S.; Zhao, Z.; Liu, H.; Liu, J.; Jiang, M.; Chen, Y.; Kwok, R. T. K.; Lam, J. W. Y.; Peng, Q.; Tang, B. Z. Mater. Chem. Fron.. 2018, 2, 1498
[31]	Yu, C.; Hao, E.; Fang, X.; Wu, Q.; Wang, L.; Li, J.; Xu, L.; Jiao, L.; Wong, W.-Y. J. Mater. Chem. C 2019, 7, 3269.
[32]	Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.
[33]	Sheldrick, G. M. Acta Crystallogr. 2015, A71, 3.
[34]	Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112.
[35]	Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01, Gaussian,Inc., Wallingford, C., 2013.

聚集诱导发光活性氟硼吡啶肼醛腙燃料的合成、晶体结构及光学性质

Aggregation-Induced Emission (AIE) Active Fluoroboronated Pyridylhydrazinyl Aldehyde Hydrozone Dyes: Synthesis, Crystal Structure and Optical Properties

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