Citation: Peipei Jiang, Tingting Zhao, Jian Rong, Bangshao Yin, Yutao Rao, Mingbo Zhou, Ling Xu, Jianxin Song. Multi-(phenylthio)porphyrinato Ni(Ⅱ) compounds: Synthesis, structures and properties[J]. Chinese Chemical Letters, ;2021, 32(8): 2562-2566. doi: 10.1016/j.cclet.2021.02.022 shu

Multi-(phenylthio)porphyrinato Ni(Ⅱ) compounds: Synthesis, structures and properties

College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, China

xulingchem@hunnu.edu.cn

jxsong@hunnu.edu.cn

Received Date: 24 December 2020
Revised Date: 2 February 2021
Accepted Date: 10 February 2021
Available Online: 15 February 2021

Figures(4)

A series of multi-(phenylthio)porphyrinato Ni(ò) compounds were synthesized without the participation of transition metal catalysts. All of these products were well characterized by ¹H NMR, ¹³C NMR and HRMS. Structures of three typical compounds were further confirmed by X-ray single crystal diffraction. Remarkable red shifts were observed in UVɃvis absorption spectra of multi-(phenylthio)porphyrinato Ni(ò) compounds which meet well with the electrochemical data. DFT calculation indicates that the phenylthio groups have strong effects on the frontier orbitals of these molecules. The order of a_1u-like and a_2u-like orbitals mainly distributed in porphyrin moiety is often inversed in energy when multi-phenylthio groups are attached.
- Phenylthio,
- Porphyrin,
- S_NAr reaction,
- a_1u/a_2u orbital
1. [1]
  (a) K.M. Kadish, K.M. Smith, R. Guilard, The Porphyrin Handbook San Diego, (2000);
  (b) C. Li, J. Zhang, J. Song, Y. Xie, J. Jiang, Sci. China Chem. 61 (2018) 511-514;
  (c) W. Miao, Z. Zhu, Z. Li, E. Hao, L. Jiao, Chin. Chem. Lett. 30 (2019) 1895-1902.
2. [2]
  (a) K. Zeng, Z. Tong, L. Ma, et al., Energy Environ. Sci. 13 (2020) 1617-1657;
  (b) A. Mahmood, J.Y. Hu, B. Xiao, et al., J. Mater. Chem. A 6 (2018) 16769-16797;
  (c) M. Urbani, M. Grätzel, M.K. Nazeeruddin, T. Torres, Chem. Rev. 114 (2014) 12330-12396;
  (d) L.L. Li, E.W.G. Diau, Chem. Soc. Rev. 42 (2013) 291-304;
  (e) Y. Rio, P. Vázquez, E. Palomares, J. Porphyrins Phthalocyanines 13 (2009) 646-651.
3. [3]
  (a) M. Pawlicki, H.A. Collins, R.G. Denning, H.L. Anderson, Angew. Chem. Int. Ed. 48 (2009) 3244-3266;
  (b) N. Aratani, D. Kim, A. Osuka, Chem. Asian J. 4 (2009) 1172-1182;
  (c) K.S. Kim, J.M. Lim, A. Osuka, D. Kim, J. Photochem. Photobiol. C 9 (2008) 13-28.
4. [4]
  (a) J. Tian, B. Huang, M.H. Nawaz, W. Zhang, Coord. Chem. Rev. 420 (2020) 213410-213429;
  (b) S.M.M. Lopes, M. Pineiro, T.M.V.D. Pinho e Melo, Molecules 25 (2020) 3450-3488;
  (c) R.D. Teo, J.Y. Hwang, J. Termini, Z. Gross, H.B. Gray, Chem. Rev. 117 (2017) 2711-2729;
  (d) M. Ethirajan, Y. Chen, P. Joshi, R.K. Pandey, Chem. Soc. Rev. 40 (2011) 340-362.
5. [5]
  M. Berthelot, G. Hoffmann, A. Bousfiha, et al., Chem. Commun. (Camb. ) 54(2018) 5414-5417. doi: 10.1039/C8CC01375F
6. [6]
  R.A. Binstead, M.J. Crossley, N.S. Hush, Inorg. Chem. 30(1991) 1259-1264. doi: 10.1021/ic00006a019
7. [7]
  M.S. Liao, S. Scheiner, Chem. Phys. Lett. 367(2003) 199-206. doi: 10.1016/S0009-2614(02)01700-1
8. [8]
  (a) L.L. Yang, X.L. Hu, Z.Q. Tang, X.F. Li, Chem. Lett. 44 (2015) 1515-1517;
  (b) D.M. Shen, C. Liu, X.G. Chen, Q.Y. Chen, J. Org. Chem. 74 (2009) 206-211.
9. [9]
  (a) A. Jana, M. Ishida, K. Kwak, et al., Chem. Eur. J. 19 (2013) 338-349;
  (b) K.A. Nielsen, E. Levillain, V.M. Lynch, J.L. Sessler, J.O. Jeppesen, Chem. Eur. J. 15 (2009) 506-516;
  (c) H. Li, J.O. Jeppesen, E. Levillain, J. Becher Chem. Commun. (2003) 846-847;
  (d) J. Becher, T. Brimert, J.O. Jeppesen, et al., Angew. Chem. Int. Ed. 40 (2001) 2497-2500;
  (e) K.I. Sugiura, K. Ushiroda, M.T. Johnson, J.S. Miller, Y. Sakata, J. Mater. Chem. 10 (2000) 2507-2514;
  (f) K.I. Sugiura, M.R. Kumar, T.K. Chandrashekar, Y. Sakata, Chem. Lett. 26 (1997) 291-292.
10. [10]
  (a) N. Fukui, A. Osuka, Bull. Chem. Soc. Jpn. 91 (2018) 1131-1137;
  (b) K. Fujimoto, H. Yorimitsu, A. Osuka, Org. Lett. 16 (2014) 972-975;
  (c) A.A. Ryan, S. Plunkett, A. Casey, T. McCabe, M.O. Senge, Chem. Commun. (Camb. ) 50 (2014) 353-355;
  (d) G.Y. Gao, A.J. Colvin, Y. Chen, X.P. Zhang, J. Org. Chem. 69 (2004) 8886-8892.
11. [11]
  (a) H.C. Sample, M.O. Senge, Eur. J. Org. Chem. 2021 (2021) 7-42;
  (b) M. Kielmann, K.J. Flanagan, K. Norvaiša, D. Intrieri, M.O. Senge, J. Org. Chem. 82 (2017) 5122-5134;
  (c) Q. Chen, Y.Z. Zhu, Q.J. Fan, S.C. Zhang, J.Y. Zheng, Org. Lett. 16 (2014) 1590-1593;
  (d) M.J. Crossley, P.L. Burn, S.S. Chew, F.B. Cuttance, I.A. Newsom, J. Chem. Soc. Chem. Commun. (1991) 1564-1566;
  (e) F. Ma, L. Zhou, Q. Liu, C. Li, Y. Xie, Org. Lett. 21 (2019) 733-736.
12. [12]
  N. Fukui, H. Yorimitsu, A. Osuka, Angew. Chem. Int. Ed. 54(2015) 6311-6314. doi: 10.1002/anie.201501149
13. [13]
  (a) A. Tsuda, H. Furuta, A. Osuka, J. Am. Chem. Soc. 123 (2001) 10304-10321;
  (b) D. Shimizu, K. Fujimoto, A. Osuka, Angew. Chem. Int. Ed. 57 (2018) 9434-9438;
  (c) K. Kato, K. Furukawa, A. Osuka, Chem. Eur. J. 24 (2018) 572-575.
14. [14]
  (a) K. Fujimoto, H. Yorimitsu, A. Osuka, Org. Lett. 16 (2014) 972-975;
  (b) K. Fujimoto, H. Yorimitsu, A. Osuka, Org. Lett. 16 (2014) 3172.
1. [1]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
2. [2]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
3. [3]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
4. [4]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
5. [5]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
6. [6]
  Xingyan Liu , Chaogang Jia , Guangmei Jiang , Chenghua Zhang , Mingzuo Chen , Xiaofei Zhao , Xiaocheng Zhang , Min Fu , Siqi Li , Jie Wu , Yiming Jia , Youzhou He . Single-atom Pd anchored in the porphyrin-center of ultrathin 2D-MOFs as the active center to enhance photocatalytic hydrogen-evolution and NO-removal. Chinese Chemical Letters, 2024, 35(9): 109455-. doi: 10.1016/j.cclet.2023.109455
7. [7]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
8. [8]
  Runze Xu , Rui Liu . U-Pb Dating in the Age of Dinosaurs. University Chemistry, 2024, 39(9): 243-247. doi: 10.12461/PKU.DXHX202404083
9. [9]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
10. [10]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108
11. [11]
  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
12. [12]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
13. [13]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
14. [14]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
15. [15]
  Mengli Xu , Zhenmin Xu , Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305
16. [16]
  Junan Pan , Xinyi Liu , Huachao Ji , Yanwei Zhu , Yanling Zhuang , Kang Chen , Ning Sun , Yongqi Liu , Yunchao Lei , Kun Wang , Bao Zang , Longlu Wang . The strategies to improve TMDs represented by MoS₂ electrocatalytic oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(11): 109515-. doi: 10.1016/j.cclet.2024.109515
17. [17]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
18. [18]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
19. [19]
  Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H₂): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329
20. [20]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(403)
HTML views(13)

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