Citation: Jiang Xindong, Yue Shuai, Chen Kepeng, Shao Zhumei, Li Chen, Su Yajun, Zhao Jianzhang. Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes: BOPYPYs[J]. Chinese Chemical Letters, ;2019, 30(12): 2271-2273. doi: 10.1016/j.cclet.2019.07.027 shu

Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes: BOPYPYs

Jiang Xindong ^a,c,*, ,
Yue Shuai ^a ,
Chen Kepeng ^b ,
Shao Zhumei ^a ,
Li Chen ^a ,
Su Yajun ^a ,
Zhao Jianzhang ^b

a.
College of Applied Chemistry, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
c.
Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526, Japan

xdjiang@syuct.edu.cn

Received Date: 14 May 2019
Revised Date: 3 July 2019
Accepted Date: 11 July 2019
Available Online: 14 December 2019

Figures(5)

Novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes (BOPYPYs) were obtained by reaction of pyrrole-2-carboxaldehyde with 1-(pyrazin-2-yl)hydrazine in the presence of Et₃N-BF₃ Et₂O for the first time. The absorption maxima of pyrazine-fused BOPYPY are obviously bathochromic shifts, in contrast to those of the reported BOPPY, indicating that the discrepant substitute groups between pyridine and pyrazine result in the remarkable wavelength difference. The new series of BOPYPYs possess high molar extinction coefficients, high fluorescence quantum yields, and larger Stokes shifts. A Knoevenagel reaction of BOPYPY with 4-dimethylaminobenzaldehyde smoothly produced the dye with the extension of π-conjugation. Dimethylamino-containing BOPYPY as a pH-responsive fluorescent sensor could detect pH value.
- BOPYPY,
- Pyrazine,
- Fluorescent dye,
- Unsymmetric,
- pH
1. [1]
  S.O. McDonnell, M.J. Hall, D.F. O'Shea, et al., J. Am. Chem. Soc. 127 (2005) 16360-16361. doi: 10.1021/ja0553497
2. [2]
  H. Lu, J. Mack, Z. Shen, et al., Chem. Soc. Rev. 43 (2014) 4778-4823. doi: 10.1039/C4CS00030G
3. [3]
  S. Long, Q. Qiao, Z. Xu, et al., Chin. Chem. Lett. 30 (2019) 573-576. doi: 10.1016/j.cclet.2018.11.031
4. [4]
  W. Liu, J. Yao, C. Zhan, Chin. Chem. Lett. 28 (2017) 875-880. doi: 10.1016/j.cclet.2017.01.013
5. [5]
  A. Xie, Z. Pan, D. Sun, et al., Chin. Chem. Lett. 30 (2019) 875-880. doi: 10.1016/j.cclet.2019.03.016
6. [6]
  Y. Cakmak, S. Kolemen, E.U. Akkaya, et al., Angew. Chem. Int. Ed. 50 (2011) 11937-11941. doi: 10.1002/anie.201105736
7. [7]
  W. Pang, X.F. Zhang, L. Jiao, et al., Chem. Commun. 48 (2012) 5437-5439. doi: 10.1039/c2cc30915g
8. [8]
  M.T. Whited, N.M. Patel, M.E. Thompson, Chem. Commun. 48 (2012) 284-286. doi: 10.1039/C1CC12260F
9. [9]
  G.M. Fischer, A.R. Ehlers, E. Daltrozzo, et al., Angew. Chem. Int. Ed. 46 (2007) 3750-3753. doi: 10.1002/anie.200604763
10. [10]
  I.S. Tamgho, A. Hasheminasab, C.J. Ziegler, et al., J. Am. Chem. Soc. 136 (2014) 5623-5625. doi: 10.1021/ja502477a
11. [11]
  C. Yu, L. Jiao, E. Hao, et al., Org. Lett. 16 (2014) 1952-1955. doi: 10.1021/ol500507f
12. [12]
  J. Wang, Q. Wu, L. Jiao, et al., J. Org. Chem. 81 (2016) 11316-11323. doi: 10.1021/acs.joc.6b02291
13. [13]
  X.D. Jiang, Y. Su, S. Yue, et al., RSC Adv. 5 (2015) 16735-16739. doi: 10.1039/C4RA15914D
14. [14]
  C. Yu, L. Jiao, E. Hao, et al., Org. Lett. 20 (2018) 4462-4466. doi: 10.1021/acs.orglett.8b01752
15. [15]
  X.D. Jiang, S. Li, B. Le Guennic, et al., Phys. Chem. Chem. Phys.18 (2016) 32686-32690. doi: 10.1039/C6CP05705E
16. [16]
  X. Jiang, T. Zhang, L. Xiao, et al., Chin. Chem. Lett. 30 (2019) 1055-1058. doi: 10.1016/j.cclet.2019.02.016
17. [17]
  X. Jiang, J. Zhao, D. Xi, et al., Chem. Eur. J. 21 (2015) 6079-6082. doi: 10.1002/chem.201406535
18. [18]
  X. Jiang, X. Liu, T. Fang, et al., Dyes Pigm. 146 (2017) 438-444. doi: 10.1016/j.dyepig.2017.07.038
19. [19]
  X. Jiang, J. Guan, J. zhao, et al., Dyes Pigm. 136 (2017) 619-626. doi: 10.1016/j.dyepig.2016.09.019
20. [20]
  T. Fang, X. Jiang, C. Sun, et al., Sens. Actuators B Chem. 290 (2019) 551-557. doi: 10.1016/j.snb.2019.03.141
21. [21]
  Q. Zheng, G. Xu, P.N. Prasad, Chem. Eur. J. 14 (2008) 5812-5819. doi: 10.1002/chem.200800309
22. [22]
  D. Wang, Y. Shiraishi, T. Hirai, Tetrahedron Lett. 51 (2010) 2545-2549. doi: 10.1016/j.tetlet.2010.03.013
23. [23]
  X. Liu, Y. Li, X. Song, et al., Chem. Commun. 54 (2018) 1509-1512. doi: 10.1039/C7CC08154E
24. [24]
  Topics in fluorescence spectroscopy, in: B. Valeur, J.R. Lakowicz (Eds.), Probe Design and Chemical Sensing, 4 Plenum, New York, 1994, pp. 21.
25. [25]
  S.O. McDonnell, D.F. O'Shea, Org. Lett. 8 (2006) 3493-3496. doi: 10.1021/ol061171x
26. [26]
  K. Rurack, M. Kollmannsberger, J. Daub, Angew. Chem. Int. Ed. 40 (2001) 385-387. doi: 10.1002/1521-3773(20010119)40:2<385::AID-ANIE385>3.0.CO;2-F
1. [1]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
2. [2]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
3. [3]
  Faqiong Zhao , Xiaohang Qiu , Yanping Ren , Juanjuan Song , Dongcheng Liu , Xiuqiong Zeng , Wenwei Zhang , Mei Shi , Min Hu , Wan Li , Yongxian Fan , Yiru Wang , Xiuyun Wang , Weihong Li , Yong Fan , Jianrong Zhang , Shuyong Zhang . The Use of pH Indicator Papers and pH Meters. University Chemistry, 2025, 40(5): 32-39. doi: 10.12461/PKU.DXHX202503099
4. [4]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
5. [5]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
6. [6]
  Jianye Kang , Xinyu Yang , Xuhao Yang , Jiahui Sun , Yuhang Liu , Shutao Wang , Wenlong Song . Carbon dots-enhanced pH-responsive lubricating hydrogel based on reversible dynamic covalent bondings. Chinese Chemical Letters, 2024, 35(5): 109297-. doi: 10.1016/j.cclet.2023.109297
7. [7]
  Shuang Li , Jiayu Sun , Guocheng Liu , Shuo Zhang , Zhong Zhang , Xiuli Wang . A new Keggin-type polyoxometallate-based bifunctional catalyst for trace detection and pH-universal photodegradation of phenol. Chinese Chemical Letters, 2024, 35(8): 109148-. doi: 10.1016/j.cclet.2023.109148
8. [8]
  Yan Liu , Yang Wang , Jiayi Zhu , Xuxian Su , Xudong Lin , Liang Xu , Xiwen Xing . Employing pH-responsive RNA triplex to control CRISPR/Cas9-mediated gene manipulation in mammalian cells. Chinese Chemical Letters, 2024, 35(9): 109427-. doi: 10.1016/j.cclet.2023.109427
9. [9]
  Tongyu Zheng , Teng Li , Xiaoyu Han , Yupei Chai , Kexin Zhao , Quan Liu , Xiaohui Ji . A DIY pH Detection Agent Using Persimmon Extract for Acid-Base Discoloration Popularization Experiment. University Chemistry, 2024, 39(5): 27-36. doi: 10.3866/PKU.DXHX202309107
10. [10]
  Jiaxu Wang , Jinxie Zhang , Xiuping Wang , Jingying Wang , Lina Chen , Jiahui Cao , Wei Cao , Siyu Liang , Ping Luan , Ke Zheng , Xiao-Kun Ouyang , Li Gao , Xiaowen Ou , Fan Zhang , Meitong Ou , Lin Mei . CaCO₃-coated hollow mesoporous silica nanoparticles for pH-responsive fungicides release. Chinese Chemical Letters, 2024, 35(12): 109697-. doi: 10.1016/j.cclet.2024.109697
11. [11]
  Yuwen Zhu , Xiang Deng , Yan Wu , Baode Shen , Lingyu Hang , Yuye Xue , Hailong Yuan . Formation mechanism of herpetrione self-assembled nanoparticles based on pH-driven method. Chinese Chemical Letters, 2025, 36(1): 109733-. doi: 10.1016/j.cclet.2024.109733
12. [12]
  Chuyuan Lin , Hui Lin , Lingxing Zeng . Optimization strategy for rechargeable Zn metal batteries over wide-pH aqueous electrolytes. Chinese Journal of Structural Chemistry, 2025, 44(1): 100407-100407. doi: 10.1016/j.cjsc.2024.100407
13. [13]
  Liang-Yu Chang , Li-Ju Xu , Dong Qiu . Shellac-based capsule for long-term controlled releasing urea with a broad soil pH tolerance. Chinese Chemical Letters, 2025, 36(5): 110034-. doi: 10.1016/j.cclet.2024.110034
14. [14]
  Hongyi Huang , Siyao Che , Wenjie Zhou , Yunchu Zhang , Weiling Zhuo , Xijing Yang , Songping Zheng , Jiagang Liu , Xiang Gao . Apatinib potentiates doxorubicin with cRGD-functionalized pH-sensitive micelles against glioma. Chinese Chemical Letters, 2025, 36(5): 110084-. doi: 10.1016/j.cclet.2024.110084
15. [15]
  Xuyun Lu , Yanan Chang , Shasha Wang , Xiaoxuan Li , Jianchun Bao , Ying Liu . Hydrogen peroxide electrosynthesis via two-electron oxygen reduction: From pH effect to device engineering. Chinese Chemical Letters, 2025, 36(5): 110277-. doi: 10.1016/j.cclet.2024.110277
16. [16]
  Di WU , Ruimeng SHI , Zhaoyang WANG , Yuehua SHI , Fan YANG , Leyong ZENG . Construction of pH/photothermal dual-responsive delivery nanosystem for combination therapy of drug-resistant bladder cancer cell. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1679-1688. doi: 10.11862/CJIC.20240135
17. [17]
  Yunjie Dang , Yanru Feng , Xiao Chen , Chaoxing He , Shujie Wei , Dingyang Liu , Jinlong Qi , Huaxing Zhang , Shaokun Yang , Zhiyun Niu , Bai Xiang . Development of a multi-level pH-responsive lipid nanoplatform for efficient co-delivery of siRNA and small-molecule drugs in tumor treatment. Chinese Chemical Letters, 2024, 35(12): 109660-. doi: 10.1016/j.cclet.2024.109660
18. [18]
  Lizhang Chen , Yu Fang , Mingxin Pang , Ruoxu Sun , Lin Xu , Qixing Zhou , Yawen Tang . Interfacial engineering of core/satellite-structured RuP/RuP2 heterojunctions for enhanced pH-universal hydrogen evolution reaction. Chinese Journal of Structural Chemistry, 2025, 44(1): 100461-100461. doi: 10.1016/j.cjsc.2024.100461
19. [19]
  Wen Zhong , Dan Zheng , Xukun Liao , Yadi Zhou , Yan Jiang , Ting Gao , Ming Li , Chengli Yang . Elaborate construction of pH-sensitive polymyxin B loaded nanoparticles for safe and effective treatment of carbapenem-resistant Klebsiella pneumoniae. Chinese Chemical Letters, 2025, 36(3): 110448-. doi: 10.1016/j.cclet.2024.110448
20. [20]
  Kaili Wang , Pengcheng Liu , Mingzhe Wang , Tianran Wei , Jitao Lu , Xingling Zhao , Zaiyong Jiang , Zhimin Yuan , Xijun Liu , Jia He . Modulating d-d orbitals coupling in PtPdCu medium-entropy alloy aerogels to boost pH-general methanol electrooxidation performance. Chinese Chemical Letters, 2025, 36(4): 110532-. doi: 10.1016/j.cclet.2024.110532

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(694)
HTML views(15)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF2) fluorescent dyes: BOPYPYs

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis, properties and application of novel 5, 6, 5, 6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF₂) fluorescent dyes: BOPYPYs