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

Baoping Hu; Qingrong Shi; Feipeng Lu; Pengcheng Zhang; Panpan Peng; Chaofeng Zhao; Yao Du; Hui Su; Shenghua Li; Siping Pang; Fudie Nie

doi:10.1055/s-0037-1611783

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(08): 910-918
DOI: 10.1055/s-0037-1611783

letter

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

Baoping Hu

^aSchool 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

^aSchool 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

^aSchool 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

^aSchool 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

^aSchool 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

^aSchool 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

^aSchool 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

^aSchool 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*

^aSchool 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*

^aSchool 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

^bInstitute of Chemical Materials, China Academy of Engineering Physics (CAEP), Mianyang, Sichuan 621900, P. R. of China

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Abstract

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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

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Referenzen

References and Notes
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43 Amino(2-benzylidenehydrazino)methaniminium 3,5-Dinitropyrazolide (4); Typical Procedure A 50 mL round-bottomed flask was charged with PhCHO (0.106 g, 1 mmol) and EtOH (6 mL) A solution of aminoguanidinium 3,5-dinitropyrazolide (0.232 g, 1 mmol) in EtOH (20 mL) was added dropwise to the flask and the resulting mixture was stirred for 7 h at 65 °C. The solvent was then slowly removed under a vacuum, and the residue was crystallized from H₂O to give light-yellow needle crystals; yield: 0.294 g (92%); mp 174.32–174.96 °C. IR (KBr): 759, 834, 1010, 1318, 1351, 486, 541, 1622, 1670, 3255 cm^–1. ¹H NMR (600 MHz, DMSO-d ₆): δ = 7.35 (s, 1 H, CH), 7.45 (s, 3 H, NH), 7.72 (t, J = 7.5 Hz, 3 H, CH), 7.87 (m, 2 H, CH), 8.22 (s, 1 H, CH,), 11.59 (s, 1 H, NH). ¹³C NMR (150 MHz, DMSO-d ₆): δ = 98.89 (s), 128.07 (s,), 129.13 (s), 130.98 (s), 133.85 (s), 147.75 (s), 155.57 (s), 156.81 (s). MS (ESI-MS): m/z = 163.05 (C₈H₁₁N₄ ⁺, cation); 156.95 (C₃HN₄O₄ ^–, anion). Anal. Calcd: C 42.25, N 34.99, H 3.78. Found: C 42.82, N 34.52, H 3.96.

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