Intermolecular Halogen and Hydrogen Bonding-Controlled Self-Assembly of Network Structures

doi:10.6023/cjoc202207007

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 705-711.DOI: 10.6023/cjoc202207007 Previous Articles Next Articles

分子间卤键和氢键控制的网络结构的组装

李芬^a, 刘传志^b^,^*(), 户志远^b, 罗盼盼^b, 崔蓉铮^b, 黄彦珂^b, 刘新明^b^,^*(), 刘澜涛^b^,^c, 吴玮^a^,^*()

a 东北石油大学化学化工学院黑龙江大庆 163318
b 商丘师范学院化学化工学院河南省药物绿色合成工程实验室河南商丘 476000
c 郑州大学化学学院郑州 450001

收稿日期:2022-07-04 修回日期:2022-09-04 发布日期:2022-10-10
基金资助:
河南省高等学校重点科研计划(21A150045); 商丘师范学院博士启动基金(700200); 商丘师范学院博士启动基金(700205)

Intermolecular Halogen and Hydrogen Bonding-Controlled Self-Assembly of Network Structures

Fen Li^a, Chuanzhi Liu^b(), Zhiyuan Hu^b, Panpan Luo^b, Rongzheng Cui^b, Yanke Huang^b, Xinming Liu^b(), Lantao Liu^b^,^c, Wei Wu^a()

a School of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing, Heilongjiang 163318
b Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000
c College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2022-07-04 Revised:2022-09-04 Published:2022-10-10
Contact: *E-mail: liuchuanzhi@sqnu.eud.cn;xmlsq@126.com;13836965068@163.com
Supported by:
Key Scientific Research Projects of Colleges and Universities of Henan Province(21A150045); Start-up Foundation for Scientific Research of Newly Recruited PhD of Shangqiu Normal University(700200); Start-up Foundation for Scientific Research of Newly Recruited PhD of Shangqiu Normal University(700205)

1. .zip(442KB)

Abstract

Two kinds of tetra-dentate halogen bonding donors were synthesized by introducing tetrafluoroiodide benzene into tetraphenylene methane and tetraphenyl porphyrin modules. 3,3',5,5'-Tetramethyl-4,4'-bipyridine (TMBP) was synthesized as halogen bonding acceptor. A type of supramolecular network structure was constructed by self-assembly of tetraphenylmethane-centered halogen donor and TMBP in solid phase based on intermolecular I…N halogen bonds and H…N hydrogen bonds. The crystal structure shows that one tetrahedral halogen bonding donor binds four TMBP molecules through two sets of I…N halogen bonds and two sets of H…N hydrogen bonds, correspondingly, one TMBP molecule binds two tetrahedral molecules through one set of I…N halogen bonds and one set of H…N hydrogen bonds to form a monolayer network structure distributed with square structures with grid width of 2.37 nm. And further stacking is controlled by other hydrogen and halogen bonds between layers. The crystal data of tetradentate halogen bonding donor molecules of porphyrins show that donor molecules assemble themselves in plane controlled by more complex weak intermolecular C-I…π and H…F interaction, and further stacking is controlled by π-π stacking between layers.

Key words: halogen bond, hydrogen bond, crystal engineering, supramolecular chemistry, self-assembly

Cite this article

Fen Li, Chuanzhi Liu, Zhiyuan Hu, Panpan Luo, Rongzheng Cui, Yanke Huang, Xinming Liu, Lantao Liu, Wei Wu. Intermolecular Halogen and Hydrogen Bonding-Controlled Self-Assembly of Network Structures[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 705-711.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

Figure 1. Structures of compounds 1~3

Scheme 1. Synthetic routes for compounds 1~3

Figure 2. Crystal structures of compounds 1 and 2

Figure 3. (a) Partial structure of one compound 1 molecule binding four TMBP molecules (H and F atoms were omitted for clarity), (b) partial structure of one TMBP molecule binding two compound 1 molecules (only the two terminal groups of compound 3 interacting with TMBP are retained, and the rest structures are omitted for clarity) and (c) a net unit of supramolecular assembly constructed by compounds 1 and 3

Figure 4. (a) Monolayer non-coplanar network structure formed in the solid phase of compounds 1 and 3, (b) side view of the network, and (c, d) bilayer stacking patterns of compounds 1 and 3 and their side view The purple balls represent iodine atoms, the light blue balls represent nitrogen atoms, and the white balls represent hydrogen atoms in (a) and (b)

Figure 5. (a) Molecular arrangement in the same layer, (b) stacking patterns between layers and (c) side view of (b)

References 13

[1]	(a) Calhorda, M. J. Chem. Commun. 2000, 801.
	(b) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48. doi: 10.1002/1521-3773(20020104)41:1【-逻辑与-】lt;48::AID-ANIE48【-逻辑与-】gt;3.0.CO;2-U
	(c) Cavallo, G.; Metrangolo, P.; Milani, R.; Pilati, T.; Priimagi, A.; Resnati, G.; Terraneo, G. Chem. Rev. 2016, 116, 2478. doi: 10.1021/acs.chemrev.5b00484
	(d) Ding, X.-H.; Chang, Y.-Z.; Ou, C.-Q.; Lin, J.-Y.; Xie, L.-H.; Huang, W. Nat. Sci. Rev. 2020, 7, 1906. doi: 10.1093/nsr/nwaa170
[2]	(a) Metrangolo, P.; Meyer, F.; Pilati, T.; Proserpio, D. M.; Resnati, G. Chem.-Eur. J. 2007, 13, 5765. doi: 10.1002/chem.200601653
	(b) Gong, G.-F.; Lv, S.-H.; Han, J.-X.; Xie, F.; Li, Q.; Xia, N.; Zeng, W.; Chen, Y.; Wang, L.; Wang, J.-K.; Chen, S.-G. Angew. Chem., Int. Ed. 2021, 60, 14831. doi: 10.1002/anie.202102448
	(c) Zheng, Q.-N.; Liu, X.-H.; Chen, T.; Yan, H.-J.; Cook, T.; Wang, D.; Stang, P. J.; Wan, L.-J. J. Am. Chem. Soc. 2015, 137, 6128. doi: 10.1021/jacs.5b02206
	(d) Pfrunder, M. C.; Brock, A. J.; Brown, J. J.; Grosjean, A.; Ward, J.; McMurtrie, J. C.; Clegg, J. K. Chem. Commun. 2018, 54, 3974 doi: 10.1039/C8CC02178C
[3]	(a) Jungbauer, S. H.; Bulfield, D.; Kniep, F.; Lehmann, C. W.; Herdtweck, E.; Huber, S. M. J. Am. Chem. Soc. 2014, 136, 16740. doi: 10.1021/ja509705f pmid: 25406545
	(b) Dumele, O.; Schreib, B.; Warzok, U.; Trapp, N.; Schalley, C. A.; Diederich, F. Angew. Chem., Int. Ed. 2016, 55, 1. pmid: 25406545
[4]	Jentzsch, A. V.; Matile, S. Top. Curr. Chem. 2015, 358, 205. doi: 10.1007/128_2014_541 pmid: 24696354
[5]	(a) Biswal, B. P.; Valligatla, S.; Wang, M-C.; Banerjee, T.; Saad, N. A.; Mariserla, B. M. K.; Chandrasekhar, N.; Becker, D.; Addicoat, M.; Senkovska, I.; Berger, R.; Rao, D. N.; Kaskel, S.; Feng, X.-L. Angew. Chem., Int. Ed. 2019, 58, 6896. doi: 10.1002/anie.201814412
	(b) Meng, Y.; Luo, Y.; Shi, J.-L.; Ding, H.-M.; Lang, X.-J.; Chen, W.; Zheng, A.-M.; Sun, J.-L.; Wang, C. Angew. Chem., Int. Ed. 2020, 59, 3624. doi: 10.1002/anie.201913091
	(c) Yang, B.; Yu, S.-B.; Zhang, P.-Q.; Wang, Z.-K.; Qi, Q.-Y.; Wang, X.-Q.; Xu, X.-H.; Yang, H.-B.; Wu, Z.-Q.; Liu, Y.; Ma, D.; Li, Z.-T. Angew. Chem., Int. Ed. 2021, 60, 26268. doi: 10.1002/anie.202112514
	(d) Yang, B.; Zhang, X.-D.; Li, J.; Tian, J.; Wu, Y.-P.; Yu, F.-X.; Wang, R.; Wang, H.; Zhang, D.-W.; Liu, Y.; Zhou, L.; Li, Z.-T. CCS Chem. 2019, 1, 156. doi: 10.31635/ccschem.019.20180011
	(e) Yu, S.-B.; Lin, F.; Tian, J.; Yu, J.; Zhang, D.-W.; Li, Z.-T. Chem. Soc. Rev. 2022, 51, 434. doi: 10.1039/D1CS00862E
[6]	(a) Muniappan, S.; Lipstmana, S.; Goldberg, I. Chem. Commun. 2008, 1777.
	(b) Syssa-Magalé, J. L.; Boubekeur, K.; Leroy, J.; Chamoreau, L. M.; Favec, C.; Schöllhorn, B. CrystEngComm 2014, 16, 10380. doi: 10.1039/C4CE01704H
	(c) Spilfogel, T. S.; Titi, H. M.; Friščić, T. Cryst. Growth Des. 2021, 21, 1810. doi: 10.1021/acs.cgd.0c01697
[7]	Gunawardana, C. A.; Ðakovićb, M.; Aakeröy, C. B. Chem. Commun. 2018, 54, 607. doi: 10.1039/C7CC08839F
[8]	Dumele, O.; Trapp, N.; Diederich, F. Angew. Chem., Int. Ed. 2015, 54, 12339. doi: 10.1002/anie.201502960
[9]	(a) Liu, C.-Z.; Koppireddi, S.; Wang, H.; Zhang, D.-W.; Li, Z.-T. Angew. Chem., Int. Ed. 2019, 58, 226. doi: 10.1002/anie.201811561
	(b) Liu, C.-Z.; Koppireddi, S.; Wang, H.; Zhang, D.-W.; Li, Z.-T. Chin. Chem. Lett. 2019, 30, 953. doi: 10.1016/j.cclet.2019.02.010
	(c) Koppireddi, S.; Liu, C.-Z.; Wang, H.; Zhang, D.-W.; Li, Z.-T. CrystEngComm 2019, 21, 2626. doi: 10.1039/c8ce02187b
[10]	Li, C.; Ren, S.-F.; Hou, J.-L.; Yi, H.-P.; Zhu, S.-Z.; Jiang, X.-K.; Li, Z.-T. Angew. Chem., Int. Ed. 2005, 44, 5725. doi: 10.1002/anie.200500982
[11]	Li, Z.; Twieg, R. J. Chem.-Eur. J. 2015, 21, 15534. doi: 10.1002/chem.201502473
[12]	Dang, Q. M.; Gilmore, S. T.; Lalwani, K.; Conk, R. J.; Simpson, J. H.; Leopold, M. C. Langmuir 2022, 38, 4747. doi: 10.1021/acs.langmuir.2c00381
[13]	Rang, A.; Engeser, M.; Maier, N. M.; Martin Nieger, M.; Lindner, W.; Schalley, C. A. Chem.-Eur. J. 2008, 14, 3855. doi: 10.1002/chem.200800113

[1]	Wenjie Zhu, Zhenchuang Xu, Yu-Cheng Gu, Yanchuan Zhao. Research Progress on Organic Cation Receptors Based on Molecular Containers [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 2991-3005.
[2]	Huiming Lu, Lamaocao Ma, Hengchang Ma. Research Progress and Prospect of Aggregation-Induced Emission Supramolecular Luminescence Materials [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4075-4105.
[3]	Deng Zhu, Zhi-Min Chen. Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3015-3032.
[4]	Jingjing Guo, Minjie Guo. Progress in Design and Application of Supramolecular Fluorescent Systems Based on Difluoroboron-Dipyrromethene and Macrocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2946-2963.
[5]	Yanyan Xu, Chuanzhi Liu, Hui Wang, Danwei Zhang, Zhanting Li. Intermolecular Halogen Bonding-Controlled Self-Assembly of Hydrogen Bonded Aromatic Amide Foldamers [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2848-2860.
[6]	Hongyu Qian, Pin He, Lu Zhang, Ke Chen, Binbin Xu, Shaoliang Lin. Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2891-2897.
[7]	Zechen Wu, Cang Cheng, Yanghui Zhang. Transition Metal-Catalyzed Reactions of C—H Bonds with Carbon Monoxide [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2155-2174.
[8]	Changxing Ji, Guangxia Wang, Hua Wang. Progress in Metal-Organic Supramolecular System Based on Subcomponent Self-Assembly [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2261-2279.
[9]	Han Ren, Ruxiang Li, Zhijian Chen, Lili Li, Hao Wang. Modification Methods and Applications of Self-Assembly Peptides [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3983-3994.
[10]	Qiang Pei, Aixiang Ding, Jinjin Wu. Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 105-125.
[11]	Ma Xiantao, Yu Jing, Wang Zilong, Zhang Yun, Zhou Qiuju. Efficient Activation of Allylic Alcohols in Pd-Catalyzed Allylic Substitution Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2669-2677.
[12]	Tian Xueqi, Zuo Minzan, Niu Pengbo, Wang Kaiya, Hu Xiaoyu. Research Advances of Host-Guest Supramolecular Self-Assemblies with Aggregration-Induced Emission Effect and Their Applications in Biomedical Field [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1823-1834.
[13]	Xiao Tangxin, Zhou Ling, Wei Xiaoyan, Li Zhengyi, Sun Xiaoqiang. Supramolecular Copolymers Driven by Quadruple Hydrogen Bonding and Host-Guest Interactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 944-949.
[14]	Huang Guobao, Chen Zhilin, Wei Xiansheng, Chen Yu, Li Xiuying, Zhong Hui, Tan Mingxiong. Recent Progress on the Construction and Function of Macrocyclic Compounds Containing Hydrogen Bond Donors [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 614-624.
[15]	Li Jing, Han Ying, Chen Chuanfeng. Recent Advances in Novel Macrocyclic Arenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3714-3737.

分子间卤键和氢键控制的网络结构的组装

Intermolecular Halogen and Hydrogen Bonding-Controlled Self-Assembly of Network Structures

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 13

Related Articles 15

Recommended Articles

Metrics

Comments