The Synthetic Routes of Bisbenz[5,6]indeno[1,2,3-cd:1′,2′,3′-lm]perylene, 5,10,15,20-tetraphenyl-, radical ion(1+)

The synthesis of bisbenz[5,6]indeno[1,2,3-cd:1′,2′,3′-lm]perylene, 5,10,15,20-tetraphenyl-, radical ion(1+) is a complex and challenging process that requires a deep understanding of organic synthesis and the ability to perform highly specialized chemical reactions.
The resulting molecule is a highly sought-after material with a wide range of potential applications in the chemical industry, and as such, the demand for a reliable and efficient synthesis route is high.

One of the most common synthetic routes for bisbenz[5,6]indeno[1,2,3-cd:1′,2′,3′-lm]perylene, 5,10,15,20-tetraphenyl-, radical ion(1+) involves a combination of chemical reactions that include Suzuki-Miyaura cross-coupling, Stille reaction, and Pd-catalyzed hydrogenation.
This route requires the use of several hazardous reagents and high temperatures and pressures, and as such, it is not without its challenges and environmental concerns.

Another synthetic route for bisbenz[5,6]indeno[1,2,3-cd:1′,2′,3′-lm]perylene, 5,10,15,20-tetraphenyl-, radical ion(1+) involves the use of a sequence of synthetic steps that include the synthesis of an indigo-type chromophore, followed by the Suzuki-Miyaura cross-coupling reaction, and finally, the Pd-catalyzed hydrogenation step.
This route is less environmentally problematic than the previous route, but it still requires the use of hazardous reagents and specialized equipment, and as such, it is not without its challenges.

Recently, a new and improved synthetic route for bisbenz[5,6]indeno[1,2,3-cd:1′,2′,3′-lm]perylene, 5,10,15,20-tetraphenyl-, radical ion(1+) has been developed that offers significant advantages over the traditional routes.
This new route involves the use of a one-pot reaction that combines the Suzuki-Miyaura cross-coupling reaction with the Pd-catalyzed hydrogenation step in a single step, using a simple and relatively inexpensive alkyl halide as the coupling partner.
This approach not only simplifies the synthetic route, but it also reduces the amount of hazardous reagents and waste generated during the synthesis, making it a more environmentally friendly method.

The new one-pot synthetic route for bisbenz[5,6]indeno[1,2,3-cd:1′,2′,3′-lm]perylene, 5,10,15,20-tetraphenyl-, radical ion(1+) begins with the preparation of the starting material, which is typically accomplished by the treatment of 4-chloronitrobenzene with a base, such as sodium hydroxide.
The resulting 4-aminonitrobenzene is then treated with a Grignard reagent, such as manganese(III) chloride, in the presence of a catalytic amount of cuprous iodide.
This results in the formation of a nitro-Grignard reagent, which is then treated with a phenylboronic acid derivative in the presence of a palladium(II) acetate catalyst.
This results in the formation of a boronate ester, which is then slowly hydrogenated over a palladium on barium sulfate catalyst at room temperature.

The resulting boronate ester can then be treated with a base, such as sodium hydroxide,