Synthesis, characterization and crystal structure of two triethylene glycol derivatives. Issue 1 (1st September 2022)

• Record Type: Journal Article
• Authors: Yang, Zaiwen; Liu, Junwei; Liu, Xiangrong; Yang, Wenzhao; Sun, Shasha; Zhao, Shunsheng; Chen, Xinjuan; Yang, Zheng; Jia, Xiaodan
• Is Part Of: Molecular crystals and liquid crystals. Volume 739:Issue 1(2023)
• Page Start: 88
• Page End: 103
• Publication Date: 2022-09-01
• Subjects: Open chain crown ether -- triethylene glycol -- crystal structure -- hydrogen bond; Molecular crystals -- Periodicals; Liquid crystals -- Periodicals; Liquid crystals; Molecular crystals; Periodicals; 548
• DOI: 10.1080/15421406.2022.2027713
• Languages: English
• ISSNs: 1542-1406

Abstract

Abstract: In this study, two compounds of triethylene glycol bistosylate (C20 H26 O8 S2, I) and 1, 8-bis(4-nitrophenoxy)-3, 6-dioxaoctane (C18 H20 N2 O8, II) were synthesized. Their structures were characterized by 1 H NMR, 13 C NMR, FT-IR, melting-point and elemental analysis, as well as X-ray single-crystal diffraction. The analyses of X-ray single crystal diffraction showed that the monomer of compound I was in sigmoid conformation due to the intramolecular C-H···π interaction, furthermore, a 3D network structure was constructed by five C-H···O hydrogen bonds. Unlike the compound I, the compound II was linked by two C-H···O hydrogen bonds through nitro and aromatic rings to form a 2D network structure. Host-guest chemistry of compounds II and β-cyclodextrin was also investigated by 1 H NMR, FT-IR and UV-Vis spectra. The binding ratio of the compound II and β -cyclodextrin was 1:2 and the association constant K a was 5.31 × 10 4 L 2 ·mol −2 obtained by UV-Vis spectra. GRAPHICAL ABSTRACT: The X-ray single-crystal structural characterization suggests that the compound I was in sigmoid conformation due to the intramolecular C-H···π interaction, furthermore, a 3D network structure was constructed by five C-H···O hydrogen bonds formed between the monomers through SO3 groups and the hydrogen atoms on the surrounding three monomers glycol. The compound II was linked by two C-H···O hydrogen bonds through nitro and aromatic rings to form a 2D network structure. UF0001 Highlights: The two triethylene glycol derivatives (compound I, compound II ) have been synthesized and characterized by 1 H NMR, IR, melting point, elemental analysis and X-ray single crystal diffraction. The single crystals of compound I and compound II were cultured, and their intermolecular solid-state structures and weak interactions were obtained by X-ray single crystal diffraction. The compound I was in special sigmoid conformation due to the intramolecular C-H···π interaction and a 3D network structure was constructed by five intermolecular C-H···O hydrogen bonds. The compound II was linked by two C-H···O hydrogen bonds through nitro and aromatic rings to form a 2D network structure. The H-bonding interactions in the compound I and compound II were studied. The host-guest chemistry between compound II and β -cyclodextrin was investigated including the apparent stoichiometry ratio and the association constant ( K a) between them.