Citation: Chunmei Zhao, Zhiying Ma, Chunli Li, Li Xu, Hua Wang. Thiophene and naphthalene-based double helix: Synthesis, structures and chirality[J]. Chinese Chemical Letters, ;2021, 32(1): 457-460. doi: 10.1016/j.cclet.2020.05.040 shu

Thiophene and naphthalene-based double helix: Synthesis, structures and chirality

Chunmei Zhao ^{a, b} ,
Zhiying Ma ^a ,
Chunli Li ^a ,
Li Xu ^{c, *} ,
Hua Wang ^{a, *}

a.
Engineering Research Center for Nanomaterials, Henan University, Kaifeng 475004, China
b.
School of Chemical Engineering and Food Science, Zhengzhou Institute of Technology, Zhengzhou 450044, China
c.
College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China

xuli@henu.edu.cn

hwang@henu.edu.cn

Received Date: 27 February 2020
Revised Date: 20 May 2020
Accepted Date: 28 May 2020
Available Online: 1 June 2020

Figures(6)

Both racemate and enantiomer of a novel double helix, binaphthylcyclooctaterthiophene (BN—COTh), which is a DNA-like molecule constructed by two single helices intertwined with each other via covalent bonds, have been synthesized with two building blocks, cycloocta-tetrathiophene (COTh) and cyclooctadinaphthyldithiophene (CONT) fused together via Negishi coupling reaction. Another homologue, dinaphthylcyclooctaterthiophene (DN-COTh) has been employed together as a model compound. Besides the synthetic work, BN—COTh and DN-COTh have been investigated by studying their crystal structures, spectroscopic behaviors, chiral resolution and chiral characteristics, including circular dichroism (CD) spectra and optical rotations. In addition, the novel crystal of enantiomer of (R, R, R)-BN—COTh has been explored. The enantiomer molecules packing along b-axis to form a larger and extended assembly packing due to intermolecular interactions between the enantiomer molecules and chloroform molecules in crystal.
- Binaphthylcyclooctaterthiophene,
- Dinaphthylcyclooctaterthiophene,
- Double helix,
- Crystal structure,
- Chirality
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