Phosphoric acid loaded azo (-N═N-) based covalent organic framework for proton conduction

J Am Chem Soc. 2014 May 7;136(18):6570-3. doi: 10.1021/ja502212v. Epub 2014 Apr 28.

Abstract

Two new chemically stable functional crystalline covalent organic frameworkds (COFs) (Tp-Azo and Tp-Stb) were synthesized using the Schiff base reaction between triformylphloroglucinol (Tp) and 4,4'-azodianiline (Azo) or 4,4'-diaminostilbene (Stb), respectively. Both COFs show the expected keto-enamine form, and high stability toward boiling water, strong acidic, and basic media. H3PO4 doping in Tp-Azo leads to immobilization of the acid within the porous framework, which facilitates proton conduction in both the hydrous (σ = 9.9 × 10(-4) S cm(-1)) and anhydrous state (σ = 6.7 × 10(-5) S cm(-1)). This report constitutes the first emergence of COFs as proton conducting materials.