Citation: Kaisheng Wang, Boyu Xiao, Ling Xu, Mingbo Zhou, Takayuki Tanaka, Atsuhiro Osuka, Jianxin Song. Nitrogen-bridged Ni(Ⅱ) porphyrinoid trimers with a central quinodiimine unit[J]. Chinese Chemical Letters, ;2022, 33(10): 4545-4548. doi: 10.1016/j.cclet.2022.01.061 shu

Nitrogen-bridged Ni(Ⅱ) porphyrinoid trimers with a central quinodiimine unit

a.
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
b.
Department of Chemistry, Graduate School of Science Kyoto University, Kyoto 606-8502, Japan

jxsong@hunnu.edu.cn

Received Date: 18 November 2021
Revised Date: 18 January 2022
Accepted Date: 23 January 2022
Available Online: 31 January 2022

Figures(7)

Buchwald-Hartwig amination of 5, 15-dibromo and 5, 10-dibromo Ni(Ⅱ)porphyrins with 5-amino Ni(Ⅱ)porphyrin gave linear and bent trimers 4Ni and 5Ni with a central quinodiimine-type Ni(Ⅱ)porphyrinoid. The structures of 4Ni and 5Ni have been confirmed by X-ray diffraction analysis in both cases. The formation of unusual products 4Ni and 5Ni has been ascribed to facile oxidation of 5, 15- and 5, 10-amino Ni(Ⅱ) porphyrin unit. Reduction of 4Ni and 5Ni under proper conditions gave NH-bridged Ni(Ⅱ)porphyrin trimers 4Ni-2H and 5Ni-2H in high yields. Trimers 4Ni and 5Ni exhibit the lowest energy band as compared with 4Ni-2H and 5Ni-2H. Especially the bent trimer 5Ni exhibits a broad absorption tail beyond 1400 nm.
- Porphyrinoid trimer,
- Aminoporphyrins,
- Buchwald-Hartwig amination,
- Reduction,
- Charge transfer
1. [1]
  A. Tsuda, A. Osuka, Science 293 (2001) 79–82. doi: 10.1126/science.1059552
2. [2]
  D. Holten, D.F. Bocian, J.S. Lindsey, Acc. Chem. Res. 35 (2002) 57–69. doi: 10.1021/ar970264z
3. [3]
  N. Aratani, D. Kim, A. Osuka, Chem. Asian J. 4 (2009) 1172–1182. doi: 10.1002/asia.200900045
4. [4]
  N. Aratani, A. Osuka, H.S. Cho, D. Kim, J. Photochem. Photobiol. C 3 (2002) 25–52. doi: 10.1016/S1389-5567(02)00003-5
5. [5]
  K.S. Kim, J.M. Lim, A. Osuka, D. Kim, J. Photochem. Photobiol. C 9 (2008) 13–28. doi: 10.5467/JKESS.2008.29.1.013
6. [6]
  K. Zeng, Z. Tong, L. Ma, et al., Energy Environ. Sci. 13 (2020) 1617–1657. doi: 10.1039/c9ee04200h
7. [7]
  Y. Rio, P. Vázquez, E. Palomares, J. Porphyrins Phthalocyanines 13 (2009) 645–651. doi: 10.1142/S1088424609000826
8. [8]
  L.L. Li, E.W.G. Diau, Chem. Soc. Rev. 42 (2013) 291–304. doi: 10.1039/C2CS35257E
9. [9]
  M. Urbani, M. Grätzel, M.K. Nazeeruddin, T. Torres, Chem. Rev. 114 (2014) 12330–12396. doi: 10.1021/cr5001964
10. [10]
  A. Mahmood, J.Y. Hu, B. Xiao, et al., J. Mater. Chem. A 6 (2018) 16769–16797. doi: 10.1039/C8TA06392C
11. [11]
  Q. Li, C. Li, J. Kim, et al., J. Am. Chem. Soc. 141 (2019) 5294–5302. doi: 10.1021/jacs.8b13148
12. [12]
  J. Yang, M.C. Yoon, H. Yoo, P. Kim, D. Kim, Chem. Soc. Rev. 41 (2012) 4808–4826. doi: 10.1039/c2cs35022j
13. [13]
  V.S.Y. Lin, S.G. DiMagno, M.J. Therien, Science 264 (1994) 1105–1111. doi: 10.1126/science.8178169
14. [14]
  T. Tanaka, A. Osuka, Chem. Soc. Rev. 44 (2015) 943–969. doi: 10.1039/C3CS60443H
15. [15]
  Q. Li, C. Li, G. Baryshnikov, et al., Nat. Commun. 11 (2020) 5289. doi: 10.1038/s41467-020-19118-9
16. [16]
  J. Tian, B. Huang, M.H. Nawaz, W. Zhang, Coord. Chem. Rev. 420 (2020) 213410–213429. doi: 10.1016/j.ccr.2020.213410
17. [17]
  M. Ethirajan, Y. Chen, P. Joshi, R.K. Pandey, Chem. Soc. Rev. 40 (2011) 340–362. doi: 10.1039/B915149B
18. [18]
  R.D. Teo, J.Y. Hwang, J. Termini, Z. Gross, H.B. Gray, Chem. Rev. 117 (2017) 2711–2729. doi: 10.1021/acs.chemrev.6b00400
19. [19]
  M. Rickhaus, A.V. Jentzsch, L. Tejerina, et al., J. Am. Chem. Soc. 139 (2017) 16502–16505. doi: 10.1021/jacs.7b10710
20. [20]
  P.S. Bols, H.L. Anderson, Acc. Chem. Res. 51 (2018) 2083–2092. doi: 10.1021/acs.accounts.8b00313
21. [21]
  O. Wennerström, H. Ericsson, I. Raston, S. Svensson, W. Pimlott, Tetrahedron Lett. 30 (1989) 1129–1132. doi: 10.1016/S0040-4039(01)80378-6
22. [22]
  J. Song, S.Y. Jang, S. Yamaguchi, et al., Angew. Chem. Int. Ed. 47 (2008) 6004–6007. doi: 10.1002/anie.200802026
23. [23]
  J. Song, N. Aratani, J.H. Heo, et al., J. Am. Chem. Soc. 132 (2010) 11868–11869. doi: 10.1021/ja1046654
24. [24]
  C. Maeda, H. Shinokubo, A. Osuka, Org. Lett. 12 (2010) 1820–1823. doi: 10.1021/ol100448x
25. [25]
  Y. Rao, J.O. Kim, W. Kim, et al., Chem. Eur. J. 22 (2016) 8801–8804. doi: 10.1002/chem.201601306
26. [26]
  M.O. Senge, M.G.H. Vicente, K.R. Gerzevske, T.P. Forsyth, K.M. Smith, Inorg. Chem. 33 (1994) 5625–5638. doi: 10.1021/ic00103a006
27. [27]
  L.J. Esdaile, M.O. Senge, D.P. Arnold, Chem. Commun. (2006) 4192–4194. doi: 10.1039/b608365j
28. [28]
  L.J. Esdaile, P. Jensen, J.C. McMurtrie, D.P. Arnold, Angew. Chem. Int. Ed. 46 (2007) 2090–2093. doi: 10.1002/anie.200604658
29. [29]
  A.M.V.M. Pereira, M.G.P.M.S. Neves, J.A.S. Cavaleiro, et al., Org. Lett. 13 (2011) 4742–4745. doi: 10.1021/ol2020658
30. [30]
  C.H. Devillers, S. Hebié, D. Lucas, et al., J. Org. Chem. 79 (2014) 6424–6434. doi: 10.1021/jo5005586
31. [31]
  A.A. Ryan, S. Plunkett, A. Casey, T. McCabe, M.O. Senge, Chem. Commun. 50 (2014) 353–355. doi: 10.1039/C3CC46828C
32. [32]
  K. Fujimoto, H. Yorimitsu, A. Osuka, Chem. Eur. J. 21 (2015) 11311–11314. doi: 10.1002/chem.201502215
33. [33]
  K. Merahi, A.M.V.M. Pereira, C. Jeandon, et al., J. Porphyrins Phthalocyanines 20 (2016) 1233–1243. doi: 10.1142/S1088424616500954
34. [34]
  D. Shimizu, K. Fujimoto, A. Osuka, Angew. Chem. Int. Ed. 57 (2018) 9434–9438. doi: 10.1002/anie.201805385
35. [35]
  N. Fukui, A. Osuka, Bull. Chem. Soc. Jpn. 91 (2018) 1131–1137. doi: 10.1246/bcsj.20180103
36. [36]
  D. Shimizu, Y. Ide, T. Ikeue, A. Osuka, Angew. Chem. Int. Ed. 58 (2019) 5023–5027. doi: 10.1002/anie.201900792
37. [37]
  K. Wang, A. Osuka, J. Song, ACS Cent. Sci. 6 (2020) 2159–2178. doi: 10.1021/acscentsci.0c01300
38. [38]
  H. Mori, J.M. Lim, D. Kim, A. Osuka, Angew. Chem. Int. Ed. 52 (2013) 12997–13001. doi: 10.1002/anie.201308545
39. [39]
  I.M. Blake, L.H. Rees, T.D.W. Claridge, H.L. Anderson, Angew. Chem. Int. Ed. 39 (2000) 1818–1821. doi: 10.1002/(SICI)1521-3773(20000515)39:10<1818::AID-ANIE1818>3.0.CO;2-E
40. [40]
  I.M. Blake, A. Krivokapic, M. Katterle, H.L. Anderson, Chem. Commun. (2002) 1662–1663.
41. [41]
  L.J. Esdaile, L. Rintoul, M.S. Goh, et al., Chem. Eur. J. 22 (2016) 3430–3446. doi: 10.1002/chem.201504252
42. [42]
  Y. Jun-i, N. Fukui, K. Furukawa, A. Osuka, Chem. Eur. J. 24 (2018) 1528–1532. doi: 10.1002/chem.201705769
1. [1]
  Qiaorui Wang , Dingyun Liang , Zhongwen Zhang , Yalan Yang , Yunran Zhang , Yirong Wang , Lei Liu , Wenfeng Jiang , Muneerah Alomar , Li-Long Zhang . Single-atom catalysts for electrocatalytic nitrogen reduction to ammonia: A review. Chinese Journal of Structural Chemistry, 2025, 44(6): 100599-100599. doi: 10.1016/j.cjsc.2025.100599
2. [2]
  Haiyan Yin , Abdusalam Ablez , Zhuangzhuang Wang , Weian Li , Yanqi Wang , Qianqian Hu , Xiaoying Huang . Novel open-framework chalcogenide photocatalysts: Cobalt cocatalyst valence state modulating critical charge transfer pathways towards high-efficiency hydrogen evolution. Chinese Journal of Structural Chemistry, 2025, 44(4): 100560-100560. doi: 10.1016/j.cjsc.2025.100560
3. [3]
  Shu-Ran Xu , Fang-Xing Xiao . Metal halide perovskites quantum dots: Synthesis, and modification strategies for solar CO2 conversion. Chinese Journal of Structural Chemistry, 2023, 42(12): 100173-100173. doi: 10.1016/j.cjsc.2023.100173
4. [4]
  Xiaobo Li , Qunyan Wu , Congzhi Wang , Jianhui Lan , Meng Zhang , Weiqun Shi . Kinetically controlled Np(Ⅵ)/Pu(Ⅳ) selective reduction by n-butyraldehyde. Chinese Chemical Letters, 2026, 37(2): 111503-. doi: 10.1016/j.cclet.2025.111503
5. [5]
  Shuqi Yu , Yu Yang , Keisuke Kuroda , Jian Pu , Rui Guo , Li-An Hou . Selective removal of Cr(Ⅵ) using polyvinylpyrrolidone and polyacrylamide co-modified MoS₂ composites by adsorption combined with reduction. Chinese Chemical Letters, 2024, 35(6): 109130-. doi: 10.1016/j.cclet.2023.109130
6. [6]
  Junqing Ye , Mengyuan Ren , Junfeng Qian , Xibao Li , Qun Chen . Advances in graphene quantum dots-based photocatalysts for enhanced charge transfer in photocatalytic reactions. Chinese Chemical Letters, 2025, 36(9): 110857-. doi: 10.1016/j.cclet.2025.110857
7. [7]
  Fengzhi Wang , Ke Hu , Jinquan Chen , Zhubin Hu , Haitao Sun , Tony D. James , Yufang Xu , Xuhong Qian . Meta-amino substituted naphthalimides exhibit large charge transfer and strong N-H vibrations enabling use as ratiometric fluorescent probe. Chinese Chemical Letters, 2026, 37(1): 110971-. doi: 10.1016/j.cclet.2025.110971
8. [8]
  Huifang Ma , Tao Xu , Saifei Yuan , Shujuan Li , Jiayao Wang , Yuping Zhang , Hao Ren , Shulai Lei . Interlayer interactions and electron transfer effects on sodium adsorption on 2D heterostructures surfaces. Chinese Chemical Letters, 2025, 36(8): 110219-. doi: 10.1016/j.cclet.2024.110219
9. [9]
  Yuchen Wang , Yaoyu Liu , Xiongfei Huang , Guanjie He , Kai Yan . Fe nanoclusters anchored in biomass waste-derived porous carbon nanosheets for high-performance supercapacitor. Chinese Chemical Letters, 2024, 35(8): 109301-. doi: 10.1016/j.cclet.2023.109301
10. [10]
  Bo Yang , Suqiong Yan , Shirong Ban , Wei Huang . New horizons in phosphorus-based emitters: From circularly polarized fluorescence to room-temperature phosphorescence. Chinese Chemical Letters, 2025, 36(11): 110837-. doi: 10.1016/j.cclet.2025.110837
11. [11]
  Ao-Hua Wang , Jun Li , Shi-Hu Du , Jia Liu , Yao Zhang , Muhammad Bilal Ahmed Siddique , Jing Chen , Shi-Bo Cheng . Beyond superhalogen assembly: Field-driven hyperhalogen design via dual-external-field cooperativity. Chinese Chemical Letters, 2026, 37(1): 111265-. doi: 10.1016/j.cclet.2025.111265
12. [12]
  Cheng-Cheng Jiao , Guang-Xing Dong , Ke Su , You-Xiang Feng , Min Zhang , Tong-Bu Lu . The construction of InVO₄/BiVO₄ heterojunction via cation-exchange for efficient and highly selective CO₂ photoreduction to methanol. Chinese Chemical Letters, 2026, 37(1): 110752-. doi: 10.1016/j.cclet.2024.110752
13. [13]
  Guodong Xu , Chengcai Sheng , Xiaomeng Zhao , Tuojiang Zhang , Zongtang Liu , Jun Dong . Reform of Comprehensive Organic Chemistry Experiments in the Context of Emerging Engineering Education: A Case Study on the Improved Preparation of Benzocaine. University Chemistry, 2024, 39(11): 286-295. doi: 10.12461/PKU.DXHX202403094
14. [14]
  Fang Niu , Rong Li , Qiaolan Zhang . Analysis of Gas-Solid Adsorption Behavior in Resistive Gas Sensing Process. University Chemistry, 2024, 39(8): 142-148. doi: 10.3866/PKU.DXHX202311102
15. [15]
  Gaopeng Liu , Lina Li , Bin Wang , Ningjie Shan , Jintao Dong , Mengxia Ji , Wenshuai Zhu , Paul K. Chu , Jiexiang Xia , Huaming Li . Construction of Bi Nanoparticles Loaded BiOCl Nanosheets Ohmic Junction for Photocatalytic CO₂ Reduction. Acta Physico-Chimica Sinica, 2024, 40(7): 2306041-0. doi: 10.3866/PKU.WHXB202306041
16. [16]
  Yushan Cai , Fang-Xing Xiao . Revisiting MXenes-based Photocatalysis Landscape: Progress, Challenges, and Future Perspectives. Acta Physico-Chimica Sinica, 2024, 40(8): 2306048-0. doi: 10.3866/PKU.WHXB202306048
17. [17]
  Xiutao Xu , Chunfeng Shao , Jinfeng Zhang , Zhongliao Wang , Kai Dai . Rational Design of S-Scheme CeO₂/Bi₂MoO₆ Microsphere Heterojunction for Efficient Photocatalytic CO₂ Reduction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309031-0. doi: 10.3866/PKU.WHXB202309031
18. [18]
  Jianyin He , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . Construction of ZnCoP/CdLa₂S₄ Schottky Heterojunctions for Enhancing Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(11): 2404030-0. doi: 10.3866/PKU.WHXB202404030
19. [19]
  Aoyun Meng , Zhenhua Li , Guoyuan Xiong , Zhen Li , Jinfeng Zhang . S-scheme heterojunction Al₆Si₂O₁₃/BiOBr with enhanced charge transfer effect for efficient and stable photocatalytic degradation of triazophos and dichlorvos pesticides. Acta Physico-Chimica Sinica, 2026, 42(5): 100186-0. doi: 10.1016/j.actphy.2025.100186
20. [20]
  Hui Li , Chunlang Gao , Guo Yang , Lu Xia , Wulyu Jiang , Cheng Wu , Kaiwen Wang , Yingtang Zhou , Xiaodong Han . Enhanced photocatalytic CO₂ reduction of Bi₂WO₆-BiOCl heterostructure with coherent interface for charge utilization. Chinese Chemical Letters, 2025, 36(9): 110547-. doi: 10.1016/j.cclet.2024.110547

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1355)
HTML views(93)

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