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Accepted Manuscript Chemistry - A European Journal 10.1002/chem.202005032 COMMUNICATION Liquid-like phase of N, N-dimethylpyrrolidinium iodide impregnated into COFs endows fast lithium ion conduction in the solid state Zhenzhen Wu,[a,b] Qinchao Xu,[c] Juan Li,[a*] and Xian-Ming Zhang[a,d*] [a] Zhenzhen Wu, Juan Li, and Prof. Dr. Xian-Ming Zhang Shanxi University Institute of Crystalline Materials Wucheng Rd., No. 92, Taiyuan 030006, China E-mail: [email protected] [b] Zhenzhen Wu Shanxi University Institute of Molecular Science [c] Qinchao Xu Chinese Academy of Science State key laboratory of Coal Conversion, Institute of Coal Chemistry 19 Kangle Street, Taiyuan 030001, China [d] Prof. Dr. Xian-Ming Zhang Shanxi Normal University School of Chemistry & Material Science 1 Gongyuan Street, Linfen 041004, P. R. China E-mail: [email protected] Abstract: A novel kind of solid-state lithium electrolyte was fabricated by impregnating organic ionic plastic crystals (OIPCs) into the pores of covalent organic frameworks (COFs). The liquid-like phase of confined N,N-dimethylpyrrolidinium iodide (P1,1I) and the ordered nanochannels of COFs simultaneously stimulated the lithium ion conduction. Organic ionic plastic crystals (OIPCs) are interesting solid state electrolyte materials for lithium batteries because of their special properties, including their thermal and electrochemical stability, fast ion transport and flexibility for chemical design. The key for Manuscript their good conductivity is their multiple reversible solid–solid phase transitions that often have larger entropy or enthalpy of Scheme 1. Schematic view of LiI@P1,1I impregnated into COFs and transition than those of the final melting transition. [1-11] The chemical structures of P1,1I and Tp-DB-COF. lithium ions can easily move via the vacancies or defects in the disordered domains. Typically, the doped lithium salt shares the same anion as OIPC and Li+ is generally considered to substitute for the plastic crystal cation within the OIPC lattice in Dry powder of P1,1I loaded COF, named after P1,1I@COFs was these systems. Doping small amount of lithium salt can lead to obtained by complete removal of methanol solvent under remarkable improvement in the ion conductivity of OIPC. vacuum. Different loading amounts were adopted to optimize the Detailed researches have proven that lithium-ion conduction was electrolyte components. The electrolytes P1,1I@COFs were the primary cause of this enhancement, which unmasked that named DMPI@COF. DMPI20@COF, DMPI40@COF, the majority of the ionic conductivity coming from Li+ ions. [12,13] DMPI60@COF, DMPI80@COF, and DMPI100@COF were In the past few years, covalent organic frameworks (COFs) have named according to the different proportions of P1,1I occupying been developed as an ideal platform to design fast ion the pore volume of Tp-DB-COF, respectively (Figure S1). conductors by the virtue of their ordered open nanochannels. [14- The powder X-ray diffraction (PXRD) patterns of the as- 21] It is found that introducing poly(ethylene oxide) (PEO) into the synthesized Tp-DB-COF and electrolyte DMPI@COFs are pores of COFs through physical or chemical methods can shown in Figure 1a. The peaks at 3.3° belong to (1 0 0) plane of Accepted induce PEO to change their phase transition behaviors Tp-DB-COF. The TEM image of Tp-DB-COF showed a large significantly why lithium ions can fasten their migration through area of regular crystal domains with oriented crystal lattice the liquid like phase. [18-21] Inspired by the phase-transition (Figure S2). After immobilization of P1,1I, the reflection peaks of behavior of PEO@COFs systems, we propose herein the Tp-DB-COF gradually disappeared and the intensity of the P1,1I loading of OIPCs based lithium electrolyte into the pore of COFs reflection peaks increased at the same time. The diffraction to fabricate a novel class of solid state lithium ion conductor. We pattern of DMPI20@COF and DMPI40@COF appeared to be fundamentally the same as that of the starting Tp-DB-COF, choose N,N-dimethylpyrrolidinium iodide (P1,1I), one of the OIPCs with two typical rotator phases here for its non-melting indicating that the framework structure of Tp-DB-COF does not characteristic and the unique static characteristic of iodide in decompose after loading the P1,1I salt. Apparent differences in [11,22,23] the relative intensities of the DMPI and Tp-DB-COF spectra P1,1I lattice. A robust COF with abundant carboxyl groups [24] indicates the presence of guest salts in the pore space of Tp- (Tp-DB-COF) was chosen to load P1,1I electrolytes. DB-COFs, similar to the reported works on ionic liquids included 1 This article is protected by copyright. All rights reserved. ChemComm View Article Online COMMUNICATION View Journal | View Issue A pre-synthetic strategy to construct single ion conductive covalent organic frameworks† Cite this: Chem. Commun., 2020, 56, 2747 Juan Li, *a Fu-Qiang Zhang,b Falian Li,a Zhenzhen Wu,a Canliang Ma,ac Received 17th January 2020, Qinchao Xu,d Pengfei Wangd and Xian-Ming Zhang*abe Accepted 29th January 2020 DOI: 10.1039/d0cc00454e rsc.li/chemcomm A pre-synthetic strategy was developed for the construction of As a novel class of porous crystalline solids, covalent organic single ion conductive covalent organic frameworks (COFs). A high frameworks (COFs) are excellent platforms for exploring single- Li+ conductivity of 1.6 Â 10À3 ScmÀ1 at 273 K was achieved, and ion conductors, which benefit from their chemical stability and single Na+ and K+ COFs were also obtained by using Na+ and K+ salts flexibility. Their ordered open channels would favor fast ion as monomers according to this synthetic method. migration in principle. Very recently, post-synthesized loading, modification and organometallic methods have been used to Crystalline porous materials, such as covalent organic frameworks construct single lithium MOFs, and good performance like (COFs), metal–organic frameworks (MOFs), zeolitic imidazolate 7.4 Â 10À3 ScmÀ1 has been achieved in those single-ion frameworks (ZIFs) and cages, have been reported as an advanced conductive MOFs and COFs,10–13,34–42 which nearly reached platform to design fast ion conductors over bulk ion conduction the practical application standard. However, we found that compounds.1–13 Their highly ordered nanochannels enable facile most of the crystalline porous single lithium conductors were electrolyte penetration and fast ion transportation through synthesized by using a post-synthetic method, but pre-synthetic them. In addition, the X-ray diffraction technique combined methods for single Li+ COFs have rarely been reported. with theoretical simulation methods can provide strong evidence In this study, we propose a pre-synthetic strategy to synthesize to establish their structure–performance relationships.2,9,14–24 single Li+ COFs by using lithium salt (lithium 2,5-diaminobenzene- Their electronically insulating framework, well-defined pore sulfonate, PaSO3Li) as the monomer. A very small amount of acetic structure, and tunable surface polarities also offer them infinite acid was used as the catalyst to avoid the possible H+/Li+ exchange Published on 29 January 2020. Downloaded by Shanxi University 5/15/2020 12:26:40 PM. possibilities for their application as candidate ion conductors in problem during the synthesis process (Scheme 1). We first synthe- 2,18–23 solid state electrolytes. sized the lithium salt PaSO3Li through the acid–base reaction of Accumulation of anions at the anode is one of the primary 2,5-diaminobenzenesulfonic acid (PaSO3H) with lithium hydroxide culprits for decreasing lithium ion battery performance over (LiOH). The complete conversion to the lithium salt was verified 1 time. In single ion solid conductors, the anions are fixed to by the H-NMR spectrum. Then PaSO3Li and triformylphloro- the underlying matrix, which prevents the sedimentation of glucinol (Tp) were condensed to form a lithium salt-based COF anions and eliminates the polarization effects present in dual (Tp-PaSO3Li-COF) through keto–enamine covalent bonds in a 25–28 ion electrolytes. Different matrixes such as polymers and solvothermal environment. The chemical structure of Tp-PaSO3Li- silicas have been adopted to construct single lithium ions.29–33 COF was characterized by solid-state 13CNMRspectrometry,FT-IR But the uncontrollability and great difficulties in synthesis spectroscopy, and powder X-ray diffraction (PXRD) analysis. In the limited the development of single Li+ conductors. 13C NMR spectrum in Fig. 1G, a sharp signal at d = 184.38 ppm (a) corresponds to the carbonyl carbon atom of the b-ketoenamine a linker. The absence of N–H stretching peaks (n = 3367 and Institute of Crystalline Materials, Shanxi University, Wucheng Rd, No. 92, À1 Taiyuan 030006, China. E-mail: [email protected], [email protected] 3293 cm ) due to the free diamine –NH2 group and of a peak À1 b Key Laboratory of Magnetic Molecules & Magnetic Information Materials due to the aldehyde group –CHO (n =1645cm )ofTpindicated (Ministry of Education), Shanxi Normal University, Linfen, 041004, China complete consumption of the reactants. The appearance of new c Institute of Molecular Science, Shanxi University, 030006, Taiyuan, China peaks at n = 1583 and 1234 cmÀ1 could be ascribed to CQCand d Institute of Coal Chemistry, Chinese Academy of Sciences, 030001 Taiyuan, China C–N stretching bands (Fig. 1F). e Institute of Chemistry and Culture, School of Chemistry & Material Science, Shanxi Normal University, Linfen 041004, China Thermogravimetric analysis (TGA) revealed that Tp-PaSO3Li-COF † Electronic supplementary information (ESI) available. See DOI: 10.1039/ showed no decomposition up to 400 1C under a nitrogen atmo- d0cc00454e sphere (Fig. S1, ESI†). The permanent porosity of Tp-PaSO3Li-COF This journal is © The Royal Society of Chemistry 2020 Chem. Commun., 2020, 56, 2747--2750 | 2747 NJC View Article Online LETTER View Journal | View Issue Layered-structure microporous poly(benzimidazole)-loaded imidazole for Cite this: New J.
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