Anthracene Carboxyimides and Their Dimers

Abstract

Soluble anthracenedicarboxyimides have been prepared and undergo a photodimerisation of the anthracene skeleton, which is important for their application as antitumour agents, such as azonafides. Reaction under strongly alkaline conditions causes C-C coupling to form soluble dimeric fluorescent dyes with bathochromic absorption and fluorescence in the NIR region. These dyes are of special interest because of their absorption at longer wavelengths.

Bisanthracene Bis(dicarboxylic imide)s as Soluble and Stable NIR Dyes

“…Therefore, herein electron‐withdrawing dicarboxylic imide groups were introduced to improve its stability as well as solubility. The partially cyclized bisanthracene bis(dicarboxylic imide)s, aceanthrene green,7, 8 has ever been synthesized and used as textile dyes and pigments with NIR absorption peak at 701 nm. One cis ‐isomer in which H is attached to the N atoms was also prepared but it co‐existed with the trans ‐isomer as a mixture.…”

“…220 °C) followed by oxidation in air or by H 2 O 2 , and the yields were usually low and most functional groups can not survive under so harsh conditions 7. 8 Therefore, improved synthetic method has to be developed to obtain sufficient materials for practical applications. For this reason, the partially fused bisanthracene bis(dicarboxylic imide)s M2 – M4 with different linking modes were also prepared in a more efficient way.…”

“…[12] The transisomer M3 was obtained in 8 % yield by heating the anthracene dicarboxylic imide 4 a in melted KOH according to a reported method. [7,8] It is interesting that treatment of 4 a using tBuOK and DBN in diglyme selectively gave the cisisomers M2 in 73 % yield and the detailed mechanisms of the selectivity are still under investigation. This simple method provided an efficient synthesis of soluble aceanthrene green cis-isomer in large scale.…”

Tunable‐Emission Amorphous Room‐Temperature Phosphorescent Polymers Based on Thermoreversible Dynamic Covalent Bonds

“…However, due to the molecular morphology, structure and other reasons, it has been rarely reported in recent years [10] . The functionalization of polycyclic aromatic hydrocarbons (PAHs) has aroused substantial attention for offering a method to manufacture π‐extended PAHs compounds as well as systems containing rigid three dimensional (3D) structures [11] . Cycloadditions of highly reactive dienophiles such as maleic anhydride and cyclopentene to PAHs can change the surface of π‐systems into compounds with a unique 3D structure [12] .…”

Anticancer, Azonafide‐Inspired Fluorescent Ligands and Their Rhenium(I) Complexes for Cellular Imaging

“…The reactivity and dimerisation of anthracene‐1,9‐dicarboximide derivatives have been reported, and anthracene‐1,9‐dicarboximide fluorophore can emit in the green part of the visible spectrum . However, it is remarkable that in the course of the biological studies of these species described earlier the fluorescent properties have not been more widely exploited in a bioimaging context.…”