Citation: Yilun Yan, Xinle Li, Gui Chen, Kai Zhang, Xihao Tang, Shuyuan Zhang, Shengrun Zheng, Jun Fan, Weiguang Zhang, Songliang Cai. Stable hydrazone-linked chiral covalent organic frameworks: Synthesis, modification, and chiral signal inversion from monomers[J]. Chinese Chemical Letters, ;2021, 32(1): 107-112. doi: 10.1016/j.cclet.2020.11.063 shu

Stable hydrazone-linked chiral covalent organic frameworks: Synthesis, modification, and chiral signal inversion from monomers

Yilun Yan ^a ,
Xinle Li ^b ,
Gui Chen ^a ,
Kai Zhang ^a ,
Xihao Tang ^a ,
Shuyuan Zhang ^a ,
Shengrun Zheng ^a ,
Jun Fan ^a ,
Weiguang Zhang ^{a, *,} ,
Songliang Cai ^{a, *,}

a.
School of Chemistry, South China Normal University, Guangzhou 510006, China
b.
Department of Chemistry, Clark Atlanta University, Atlanta, Georgia 30314, United States

wgzhang@scnu.edu.cn

songliangcai@m.scnu.edu.cn

Received Date: 28 June 2020
Revised Date: 18 November 2020
Accepted Date: 18 November 2020
Available Online: 1 December 2020

Figures(5)

The designed synthesis of chiral covalent organic frameworks (COFs) featuring intriguing properties is fairly scant and remains a daunting synthetic challenge. Here we develop a de novo synthesis of an enantiomeric pair of 2D hydroxyl-functionalized hydrazone-linked chiral COFs, (S)- and (R)-HthBta-OH COFs, using enantiopure 2, 5-bis(2-hydroxypropoxy)terephthalohydrazide (Hth) as monomers. The formation process of hydroxyl-functionalized chiral COFs was monitored using rigorous time-dependent PXRD, vibrational circular dichroism (VCD), and electronic circular dichroism (ECD) studies. Remarkably, VCD spectra indicated a unique chiral signal inversion from the positive Cotton effect of (S)-Hth monomer to the negative Cotton effect of (S)-HthBta-OH COF, which has never been reported in chiral COFs. Moreover, two unprecedented carboxyl-functionalized chiral COFs, (S)- and (R)-HthBta-COOH, were constructed by a post-synthetic modification of the corresponding hydroxyl chiral COFs with succinic anhydride. Notably, carboxyl-functionalized COFs retained homochirality and crystallinity without linker racemization and structural collapse after the chemical modification due to the chemically robust nature of pristine hydrazone-linked chiral COFs.
- Chiral covalent organic frameworks,
- De novo synthesis,
- Post-synthetic modification,
- Chiral signal inversion
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