Cover Feature: Oxygen‐Doped PAH Electrochromes: Difurano, Dipyrano, and Furano‐Pyrano Containing Naphthalene‐Cored Molecules (Eur. J. Org. Chem. 2/2022)

Abstract

The Cover Feature shows the color changes achieved, upon oxidation, by newly synthesized electrochromic oxygen‐doped small molecules. The crucial moieties are furano and pyrano. Incorporation of these groups into other organic molecules can be used to greatly expand the library of electrochromic small molecules, giving very good control over color transition observed. Such controlled color changes could take electrochromism from the niche applications it currently occupies, to the wider world. Cover design by Adriana Lopez‐Biagi. More information can be found in the Full Paper by D. Bonifazi et al.

Polycarbazole Electropolymerization Materials with Excellent Electrochromic Performance Based on Phenothiazine/Phenoxazine Group

“…The monomer CZ-FSQ and CZ-FEQ were obtained by Suzuki-coupling reaction. 1 H NMR spectra and mass spectra confirmed that the target molecules were obtained correctly. The synthesis and characterization details of the target molecules and their precursors are shown in the experimental section.…”

“…Finally, 0.45 g of white solid was obtained in 28% yield. 1 3 mmol), K 2 CO 3 (0.64 g, 4.6 mmol), and 18-Crown-6 (5% mol) in a 100 mL twoneck round bottom flask under N 2 protection. Then acetone (50 mL) was injected with a syringe.…”

“…Finally, 0.4 g of white solid was obtained in 47% yield. 1 3,7-Dibromo-10-methyl-10H-phenothiazine (3): The synthesis method is referred to the previous literature. [28] 10-Methyl-10H-phenothiazine (0.4 g, 1.8 mmol) and NBS (0.8 g, 4 mmol) were dissolved in toluene (20 mL).…”

“…The crude product was column chromatographed on silica gel (200-300 mesh, petroleum ether/dichloromethane: 10/1) to give compound 3, 0.6 g as a white solid (yield: 86%). 1 6): [29] To a solution of 3 (1.93 g, 5.20 mmol) in dry THF (24 mL) under N 2 protection was added nbutyllithium (1.6 m in hexane, 8.16 mL, 12.94 mmol) at −78 °C and the mixture was allowed to react for 1 h at that temperature. Then 2-isopropoxy 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.20 mL, 0.622 mmol) was added and the mixture was stirred at room temperature overnight.…”

“…Electrochromism is the phenomenon of reversible color change in the appearance of a material under the action of an applied voltage. [1][2][3] Electrochromic materials are widely used in many fields such as aircraft portholes, electronic paper, glass curtain walls, etc., and have great development prospects. [4] The currently used organic electrochromic materials can be divided into organic small molecules and conductive polymers.…”