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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 2: 705 - 711

DOI: https://doi.org/10.6023/cjoc202207007

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

  • Fen Li ,
  • Chuanzhi Liu ,
  • Zhiyuan Hu ,
  • Panpan Luo ,
  • Rongzheng Cui ,
  • Yanke Huang ,
  • Xinming Liu ,
  • Lantao Liu ,
  • Wei Wu
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  • 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
* Corresponding authors. E-mail: ;
;

Received date: 2022-07-04

  Revised date: 2022-09-04

  Online published: 2022-10-10

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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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 . DOI: 10.6023/cjoc202207007

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