Citation: Xiang GAO, Qiushui MU, Yuejian LIN, Guoxin JIN. A synthetic strategy of organometallic supramolecular bridged compounds and spirocyclic compounds featuring half-sandwich Cp*Rh units[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(1): 164-172. doi: 10.11862/CJIC.20230356 shu

A synthetic strategy of organometallic supramolecular bridged compounds and spirocyclic compounds featuring half-sandwich Cp*Rh units

Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, State Key Laboratory of Molecular Engineering of Polymers, Fudan University, Shanghai 200438, China

Corresponding author: Guoxin JIN, gxjin@fudan.edu.cn
Received Date: 26 September 2023
Revised Date: 27 November 2023

Figures(8)

Bridged and spirocyclic compounds are common concepts in the pure organic field. Herein, we extend these concepts to supramolecular chemistry and a synthetic strategy is exhibited. Three supramolecular bridged compounds [(Cp*Rh)₆(μ-η²-η²-C₂O₄)₂(μ-C₂O₄)(L^A)₂](OTf)₆ (1), [(Cp*Rh)₆(dhbq)₂(pyrazine)(L^A)₂](OTf)₈ (2), and [(Cp*Rh)₆ (tpphz)₂(bpea)(L^A)₂](OTf)₁₂ (3), and a spirocyclic compound (Cp*Rh)₁₂(bibzim)₃Ru(L^A)₃(L^B)₃](OTf)₁₀(PF₆)₄ (4), where L^A =3,3′-di(pyridin-4-yl)-2,2′-bipyridine, OTf^-=CF₃SO³^-, dhbq=2,5-dihydroxy-1,4-benzoquinone, tpphz=tetrapyrido[3,2-a∶2′,3′-c∶3″, 2″-h∶2''',3'''-j]phenazine, bpea=1,2-di(pyridin-4-yl)ethane, bibzim=2,2′-bisbenzimidazole, L^B=4,4′-di(pyridin-4-yl)-1,1′-biphenyl, were obtained by introducing of additional chelating sites in rigid linear ligand through coordination-driven stepwise chemical self-assembly method and were characterized by single crystal X-ray diffraction method.
- self-assembly,
- macrocycles,
- coordination-driven,
- bridged compounds,
- spirocyclic compounds
1. [1]
  XING Q Y, PEI W W, XU R Q, PEI J. Basic organic chemistry. 3rd ed. Beijing: Higher Education Press, 2005: 42-46
2. [2]
  Xia D Y, Wang P, Ji X F, Khashab N M, Sessler J L, Huang F H. Functional supramolecular polymeric networks: The marriage of covalent polymers and macrocycle-based host-guest interactions[J]. Chem. Rev., 2020,120:607-6123.
3. [3]
  Aucagne V, Berná J, Crowley J D, Goldup S M, Hänni K D, Leigh D A, Lusby P J, Ronaldson V E, Slawin A M Z, Viterisi A, Walker D B. Catalytic "active-metal" template synthesis of[2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the Cu(Ⅰ)-catalyzed azide-alkyne 1,3-cycloaddition[J]. J. Am. Chem. Soc., 2007,129:11950-11963. doi: 10.1021/ja073513f
4. [4]
  Cai K, Mao H C, Liu W G, Qiu Y Y, Shi Y, Zhang L, Shen D K, Chen H L, Jiao Y, Wu H, Liu Z C, Feng Y N, Stern C L, Wasielewski M R, Goddard Ⅲ W A, Stoddart J F. Highly stable organic bisradicals protected by mechanical bonds[J]. J. Am. Chem. Soc., 2020,142:7190-7197. doi: 10.1021/jacs.0c01989
5. [5]
  Gao W X, Feng H J, Guo B B, Lu Y, Jin G X. Coordination-directed construction of molecular links[J]. Chem. Rev., 2020,120:6288-6325. doi: 10.1021/acs.chemrev.0c00321
6. [6]
  Fujita M, Tominaga M, Hori A, Therrien B. Coordination assemblies from a Pd(Ⅱ)-cornered square complex[J]. Acc. Chem. Res., 2005,38:369-378. doi: 10.1021/ar040153h
7. [7]
  Kaim W, Schwederski B, Dogan A, Fiedler J, Kuehl C J, Stang P J. Metalla-supramolecular rectangles as electron reservoirs for multielectron reduction and oxidation[J]. Inorg. Chem., 2002,41:4025-4028. doi: 10.1021/ic020122n
8. [8]
  Han Y F, Lin Y J, Jia W G, Jin G X. Synthesis, structure and electrochemical properties of molecular rectangles of half-sandwich iridium complexes containing the bridging chioranilate ligands[J]. Organometallics, 2008,27:4088-4097. doi: 10.1021/om800426e
9. [9]
  Gao X, Cui Z, Shen Y R, Liu D, Lin Y J, Jin G X. Synthesis and near-infrared photothermal conversion of discrete supramolecular topologies featuring half-sandwich[Cp*Rh]units[J]. J. Am. Chem. Soc., 2021,143:17833-17842. doi: 10.1021/jacs.1c09333
10. [10]
  Shen Y R, Gao X, Cui Z, Jin G X. Rational design and synthesis of interlocked [2]catenanes featuring half-sandwich Cp*Rh/Ir units and pyrene-based ligands[J]. Chin. J. Chem., 2021,39:3303-3308. doi: 10.1002/cjoc.202100546
11. [11]
  Zhang H N, Lin Y J, Jin G X. Selective construction of very large stacking-interaction-induced molecular 8₁₈ metalla-knots and Borromean ring using curved dipyridyl ligands[J]. J. Am. Chem. Soc., 2021,143:1119-1125. doi: 10.1021/jacs.0c11925
12. [12]
  Dang L L, Feng H J, Lin Y J, Jin G X. Self-assembly of molecular figure-eight knots induced by quadruple stacking interactions[J]. J. Am. Chem. Soc., 2020,142:18946-18954. doi: 10.1021/jacs.0c09162
13. [13]
  Dang L L, Zhang T T, Chen T, Zhao Y, Gao X, Aznarez M, Ma L F, Jin G X. Selective synthesis and structural transformation of a 4-ravel containing four crossings and featuring Cp*Rh/Ir fragments[J]. Angew. Chem. Int. Ed., 2023,62e20230151.
14. [14]
  Han Y F, Lin Y J, Weng L H, Berke H, Jin G X. Stepwise assembly of "organometallic boxes" with half-sandwich Ir, Rh and Ru fragments[J]. Chem. Commun., 2008:350-352.
15. [15]
  Han Y F, Lin Y J, Jin G X. Template-controlled topochemical photodimerization based on "organometallic macrocycles" through single-crystal-to-single-crystal transformation[J]. Chem. Commun., 2008:1807-1809.
16. [16]
  Han Y F, Jia W G, Lin Y J, Jin G X. Stepwise formation of molecular rectangular boxes of half-sandwich rhodium and ruthenium complexes containing bridging chloranilate ligands[J]. Organometallics, 2008,27:5002-5008. doi: 10.1021/om800490s
17. [17]
  Zhang H N, Gao W X, Deng Y X, Lin Y J, Jin G X. Stacking-interaction-induced host-guest chemistry and Borromean rings based on a polypyridyl ligand[J]. Chem. Commun., 2018,54:1559-1562. doi: 10.1039/C7CC09448E
18. [18]
  Wu T, Lin Y J, Jin G X. Stepwise formation of organometallic macrocycles and triangular prisms containing 2, 2'-bisbenzimidazole ligands[J]. Dalton Trans., 2013,42:82-88. doi: 10.1039/C2DT31387A
19. [19]
  Iranmanesh H, Arachchige K S A, Bhadbhade M, Donald W A, Liew J A, Liu K T C, Luis E T, Moore E G, Price J R, Yan H, Yang J J, Beves J E. Chiral ruthenium(Ⅱ) complexes as supramolecular building blocks for heterometallic self-assembly[J]. Inorg. Chem., 2016,55:12737-12751. doi: 10.1021/acs.inorgchem.6b02007
20. [20]
  Liu D, Lu Y, Lin Y J, Jin G X. Rational design and integrative assembly of heteromeric metalla[2]catenanes featuring Cp*Ir/Rh fragments[J]. Chem.-Eur. J., 2022,28e202104617. doi: 10.1002/chem.202104617
21. [21]
  Hu C C, Chen Y Y. Chemoselective and fast decarboxylative allylation by photoredox catalysis under mild conditions[J]. Org. Chem. Front., 2015,2:1352-1355. doi: 10.1039/C5QO00187K
1. [1]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
2. [2]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
3. [3]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
4. [4]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
5. [5]
  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
6. [6]
  Zhenyang Lin . A classification scheme for inorganic cluster compounds based on their electronic structures and bonding characteristics. Chinese Journal of Structural Chemistry, 2024, 43(5): 100254-100254. doi: 10.1016/j.cjsc.2024.100254
7. [7]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
8. [8]
  Wen-Hui Mi , Teng-Yu Huang , Yu-Fei Ao , Xu-Dong Wang , Qi-Qiang Wang , De-Xian Wang . Ultracycles consisting of macrocycles. Chinese Chemical Letters, 2024, 35(5): 109077-. doi: 10.1016/j.cclet.2023.109077
9. [9]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
10. [10]
  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
11. [11]
  Dong-Sheng Deng , Su-Qin Tang , Yong-Tu Yuan , Ding-Xiong Xie , Zhi-Yuan Zhu , Yue-Mei Huang , Yun-Lin Liu . C-F insertion reaction sheds new light on the construction of fluorinated compounds. Chinese Chemical Letters, 2024, 35(8): 109417-. doi: 10.1016/j.cclet.2023.109417
12. [12]
  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
13. [13]
  Zeyu Jiang , Yadi Wang , Changwei Chen , Chi He . Progress and challenge of functional single-atom catalysts for the catalytic oxidation of volatile organic compounds. Chinese Chemical Letters, 2024, 35(9): 109400-. doi: 10.1016/j.cclet.2023.109400
14. [14]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
15. [15]
  Hualei Xu , Manman Han , Haiqiang Liu , Liang Qin , Lulu Chen , Hao Hu , Ran Wu , Chenyu Yang , Hua Guo , Jinrong Li , Jinxiang Fu , Qichen Hao , Yijun Zhou , Jinchao Feng , Xiaodong Wang . 4-Nitrocatechol as a novel matrix for low-molecular-weight compounds in situ detection and imaging in biological tissues by MALDI-MSI. Chinese Chemical Letters, 2024, 35(6): 109095-. doi: 10.1016/j.cclet.2023.109095
16. [16]
  Ze-Yuan Ma , Mei Xiao , Cheng-Kun Li , Adedamola Shoberu , Jian-Ping Zou . S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076
17. [17]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
18. [18]
  Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306
19. [19]
  Yanbing Shen , Yuan Yuan , Yaxin Wang , Xiaonan Ma , Wensheng Yang , Yulan Chen . Dihydroanthracene bridged bis-naphthopyrans: A multimodal chromophore with mechano- and photo-chromic properties. Chinese Chemical Letters, 2024, 35(5): 108949-. doi: 10.1016/j.cclet.2023.108949
20. [20]
  Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(395)
HTML views(43)

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