分子间卤键和氢键控制的网络结构的组装

doi:10.6023/cjoc202207007

有机化学 ›› 2023, Vol. 43 ›› Issue (2): 705-711.DOI: 10.6023/cjoc202207007 上一篇下一篇

研究论文

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)

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摘要/Abstract

分别以四苯甲烷和四苯基卟啉为中心, 端位引入四氟碘代苯, 合成了两类四齿卤键供体分子, 并合成了3,3',5,5'-四甲基-4,4'-联吡啶(TMBP)作为卤键受体分子. 以四苯甲烷为中心的卤键供体分子和TMBP基于分子间I…N卤键和H…N氢键在固相中自组装, 得到一类超分子网络结构. 晶体结构显示, 一个四面体卤键供体分子通过两组I…N卤键和两组H…N氢键结合四个TMBP分子, 与之对应, 一个TMBP分子通过一组I…N卤键和一组H…N氢键结合两个四面体分子, 形成单层网络结构, 网格为宽度2.37 nm的正方形结构, 层与层之间通过其它氢键和卤键进一步堆积. 卟啉类四齿卤键供体分子的晶体数据显示, 通过较为复杂的分子间C-I…π及H…F等弱相互作用, 供体分子自身进行平面组装, 层与层之间通过π-π堆积等作用进一步堆积.

关键词: 卤键, 氢键, 晶体工程, 超分子化学, 自组装

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

引用此文

李芬, 刘传志, 户志远, 罗盼盼, 崔蓉铮, 黄彦珂, 刘新明, 刘澜涛, 吴玮. 分子间卤键和氢键控制的网络结构的组装[J]. 有机化学, 2023, 43(2): 705-711.

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.

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图/表 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)

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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

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