An electron-deficient MOF as an efficient electron-transfer catalyst for selective oxidative carbon–carbon coupling of 2,6-di-tert-butylphenol

Abstract

Naphthalene diimides (NDIs), a type of electron-deficient dye molecule with high quadrupole moment and excellent redox activity, have been utilized in various fields, such as energy transfer, chemical sensing, anion transport, and photo-/electrochromic materials. In this study, an electron-deficient metal–organic framework with one-dimensional channels, Eu₂(BBNDI)₃(DMF)₂ (MOF 1) (H₂BBNDI = N,N′-bis(3-benzoic acid)naphthalene diimide), was successfully constructed based on the naphthalene diimide derivative. Because of the generation of NDI radicals by electron transfer between components, this material exhibits fast-responsive reversible photochromic properties. Moreover, it shows high efficiency and selective oxidation of 2,6-di-tert-butylphenol to its quinone derivative, aldehyde, and dimeric or trimeric phenol derivative by controlling the reaction conditions.