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Synlett 2019; 30(08): 910-918
DOI: 10.1055/s-0037-1611783
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© Georg Thieme Verlag Stuttgart · New York

General and Greener Synthesis of Diverse Functional Organic Salts through Schiff Base Chemistry

Baoping Hu
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Qingrong Shi
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Feipeng Lu
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Pengcheng Zhang
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Panpan Peng
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Chaofeng Zhao
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Yao Du
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Hui Su
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Shenghua Li*
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Siping Pang*
a   School of Materials Science and Engineering, Beijing Institute of Technology, South Street No. 5, Zhongguancun, Haidian District, Beijing, 100081, P. R. of China   Email: lishenghua@bit.edu.cn   Email: pangsp@bit.edu.cn
,
Fudie Nie
b   Institute of Chemical Materials, China Academy of Engineering Physics (CAEP), Mianyang, Sichuan 621900, P. R. of China
› Author AffiliationsThe authors acknowledge financial support from NSAF (U1530262), the National Natural Science Foundation of China (21875021 and 21576026), and the Fundamental Research Funds for the Central Universities.
Further Information

Publication History

Received: 20 February 2019

Accepted after revision: 14 March 2019

Publication Date:
16 April 2019 (online)

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Abstract

We report a greener and more-general organic method for the synthesis of functional organic salts containing organic anions through a Schiff base reaction between readily available aldehydes and simple aminoguanidinium salts. This reaction is operationally simple, free of metal salts, and forms water as the sole byproduct. The broad scope and good functional-group compatibility of this method permit its use to provide ready access to a library of more than 70 distinct organic salts, including those of heterocyclic anions, complex pharmaceutical anions, and polyanions, which are difficult to obtain through classical inorganic methods. Moreover, choosing different aldehydes and organic anions provides a convenient method for modulating or improving the functional properties of the designed organic salts, such as their melting points, fluorescence, and energetic properties. We therefore expect that this method will open new opportunities for the discovery and functionalization of a wide variety of organic salts and functional materials.

Key words

organic salts - Schiff base reaction - functional materials

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611783.
  • Supporting Information
 

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