Citation: Tan Shuai, Wu Xiugang, Zheng Yanqiong, Wang Yafei. Synthesis and properties of novel N, C, N terdentate skeleton based on 1, 3-di(pyridin-2-yl)benzene moiety-new tricks for old dogs[J]. Chinese Chemical Letters, ;2019, 30(11): 1951-1954. doi: 10.1016/j.cclet.2019.08.003 shu

Synthesis and properties of novel N, C, N terdentate skeleton based on 1, 3-di(pyridin-2-yl)benzene moiety-new tricks for old dogs

Tan Shuai ^b,1 ,
Wu Xiugang ^a,1 ,
Zheng Yanqiong ^c ,
Wang Yafei ^a,b,*,

a.
Jiangsu Engineering Laboratory of Light-Electricity-Heat Energy-Converting Materials and Applications, Jiangsu Key Laboratory of Environmentally Friendly Polymeric Materials, Jiangsu Collaboration Innovation Center of Photovoltaic Science and Engineering, School of Materials Science & Engineering, Changzhou University, Changzhou 213164, China
b.
College of Chemistry, Key Lab of Environment-Friendly Chemistry and Application of the Ministry of Education, Xiangtan University, Xiangtan 411105, China
c.
Key Laboratory of Advanced Display and System Applications of Ministry of Education, Shanghai University, Shanghai 200072, China

qiji830404@hotmail.com

Received Date: 3 July 2019
Revised Date: 27 July 2019
Accepted Date: 3 August 2019
Available Online: 5 November 2019

Figures(7)

Utilization of intermolecular Friedel-Crafts and intramolecular condensation reaction, novel 1, 3-di-(pyridine-2-yl)benzene(N, C, N terdentate) skeleton with electro-withdrawing group in 6' position of pyridyl and a cyclization between 6' position of pyridyl and 6 position of benzyl ring were firstly designed and synthesized. The structures of these novel N, C, N terdentate were confirmed by NMR, MS and X-ray single crystalanalyses. The photophysical properties of these compounds were briefly explored.
- 1, 3-Di(pyridin-2-yl)benzene skeleton,
- Platinum complex,
- Synthesis,
- Intramolecular cyclization
1. [1]
  G.W.V. Cave, N.W. Alcock, J.P. Rourke, Organometallics 18(1999) 1801-1803. doi: 10.1021/om981006o
2. [2]
  K.H. Wong, K.K. Cheung, M.C.W. Chan, C.M. Che, Organometallics 17(1998) 3505-3511. doi: 10.1021/om980274j
3. [3]
  W. Lu, B.X. Mi, M.C.W. Chan, et al., J. Am. Chem. Soc. 126(2004) 4958-4971. doi: 10.1021/ja0317776
4. [4]
  M.G. Lagunas, R.A. Gossage, W.J.J. Smeets, A.L. Spek, G.V. Koten, Eur. J. Inorg. Chem. 1998(1998) 163-168.
5. [5]
  P.G. Bomben, K.C.D. Robson, P.A. Sedach, C.P. Berlinguette, Inorg. Chem. 48(2009) 9631-9643. doi: 10.1021/ic900653q
6. [6]
  S. Katagiri, R. Sakamoto, H. Maeda, et al., Chem.-Eur. J. 19(2013) 5088-5096. doi: 10.1002/chem.201203913
7. [7]
  T.R. Papo, D. Jaganyi, J. Coord. Chem. 68(2015) 794-807. doi: 10.1080/00958972.2014.1001752
8. [8]
  A. Colombo, F. Fiorini, D. Septiadi, et al., Dalton Trans. 44(2015) 8478-8487. doi: 10.1039/C4DT03165B
9. [9]
  K. Ogata, D. Sasano, T. Yokoi, et al., Chem.-Eur. J. 19(2013) 12356-12375. doi: 10.1002/chem.201301513
10. [10]
  T. Fu, L. Ao, Z. Gao, X. Zhang, F. Wang, Chin. Chem. Lett. 27(2016) 1147-1154. doi: 10.1016/j.cclet.2016.06.054
11. [11]
  D. Choi, T. Kim, S.M. Reddy, J. Kang, Inorg. Chem. Commun. 12(2009) 41-44. doi: 10.1016/j.inoche.2008.10.026
12. [12]
  X. Kan, H. Liu, Q. Pan, Z. Li, Y. Zhao, Chin. Chem. Lett. 29(2018) 261-266. doi: 10.1016/j.cclet.2017.08.042
13. [13]
  J.G. Cai, Z.T. Yu, Y.J. Yuan, F. Li, Z.G. Zou, ACS Catal. 4(2014) 1953-1963. doi: 10.1021/cs500296s
14. [14]
  T.W. Rees, J. Liao, A. Sinopoli, et al., Inorg. Chem. 56(2017) 9903-9912. doi: 10.1021/acs.inorgchem.7b01412
15. [15]
  B.D. Koivisto, K.C.D. Robson, C.P. Berlinguette, Inorg. Chem. 48(2009) 9644-9652. doi: 10.1021/ic9007137
16. [16]
  K.C. Robson, P.G. Bomben, C.P. Berlinguette, Dalton Trans. 41(2012) 7814-7829. doi: 10.1039/c2dt30825h
17. [17]
  J. Lin, N.Y. Chau, J.L. Liao, et al., Organometallics 35(2016) 1813-1824. doi: 10.1021/acs.organomet.6b00205
18. [18]
  D.A. Patrick, M.A. Ismail, R.K. Arafa, et al., J. Med. Chem. 56(2013) 5473-5494. doi: 10.1021/jm400508e
19. [19]
  B. Tong, H.Y. Ku, I.J. Chen, et al., J. Mater. Chem. C 3(2015) 3460-3471. doi: 10.1039/C5TC00163C
20. [20]
  T.R. Papo, D. Jaganyi, Transition Metal Chem. 40(2014) 53-60.
21. [21]
  J.A.G. Williams, A. Beeby, E.S. Davies, J.A. Weinstein, C. Wilson, Inorg. Chem. 42(2003) 8609-8611. doi: 10.1021/ic035083+
22. [22]
  Z.L. Gong, Y.W. Zhong, Organometallics 32(2013) 7495-7502. doi: 10.1021/om400999h
23. [23]
  Z. Wang, E. Turner, V. Mahoney, et al., Inorg. Chem. 49(2010) 11276-11286. doi: 10.1021/ic100740e
24. [24]
  S. Ott, M. Borgstrom, L. Hammarstrom, O. Johansson, Dalton Trans. 2006(2006) 1434-1443.
25. [25]
  J. Uchida, M. Yoshio, S. Sato, et al., Angew. Chem. 56(2017) 14085-14089. doi: 10.1002/anie.201707740
26. [26]
  M. Cocchi, D. Virgili, V. Fattori, D.L. Rochester, J.A.G. Williams, Adv. Func. Mater. 17(2007) 285-289. doi: 10.1002/adfm.200600167
27. [27]
  S.J. Choi, J. Kuwabara, Y. Nishimura, T. Arai, T. Kanbara, Chem. Lett. 41(2012) 65-67. doi: 10.1246/cl.2012.65
28. [28]
  B. Avitia, E. MacIntosh, S. Muhia, E. Kelson, Tetrahedron Lett. 52(2011) 1631-1634. doi: 10.1016/j.tetlet.2011.01.136
29. [29]
  L.F. Gildea, A.S. Batsanov, J.A. Williams, Dalton Trans. 42(2013) 10388-10393. doi: 10.1039/c3dt51211h
30. [30]
  J. Pawlas, M. Begtrup, Org. Lett. 4(2002) 2687-2690. doi: 10.1021/ol026197c
31. [31]
  G. Dyker, M. Gabler, M. Nouroozian, P. Schulz, Tetrahedron Lett. 35(1994) 9697-9700. doi: 10.1016/0040-4039(94)88362-9
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
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]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
6. [6]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
7. [7]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
8. [8]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
9. [9]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
10. [10]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
11. [11]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
12. [12]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
13. [13]
  Pingping HAO , Fangfang LI , Yawen WANG , Houfen LI , Xiao ZHANG , Rui LI , Lei WANG , Jianxin LIU . Hydrogen production performance of the non-platinum-based MoS₂/CuS cathode in microbial electrolytic cells. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1811-1824. doi: 10.11862/CJIC.20240054
14. [14]
  Rongjian Chen , Jiahui Liu , Caixia Lin , Yuanming Li , Yanhou Geng , Yaofeng Yuan . Synthesis and properties of tetraphenylethene cationic cyclophanes based on o-carborane skeleton. Chinese Chemical Letters, 2024, 35(12): 110074-. doi: 10.1016/j.cclet.2024.110074
15. [15]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
16. [16]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
17. [17]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
18. [18]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
19. [19]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
20. [20]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(945)
HTML views(52)

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