The Synthetic Routes of 9-([1,1-biphenyl]-3-yl)-9H-carbazole

The synthesis of novel chemical compounds is a crucial aspect of the chemical industry, as it plays a vital role in the development of new materials, medicines, and other products.
One such compound is 9-([1,1-biphenyl]-3-yl)-9H-carbazole, which has shown promising properties as a material for organic electronic devices, such as organic field-effect transistors (OFETs) and organic solar cells.

There are several synthetic routes available for the production of 9-([1,1-biphenyl]-3-yl)-9H-carbazole, each with its own advantages and disadvantages.
In this article, we will discuss three of the most common synthetic routes for this compound: the classical route, the modern route, and the green route.

Classical Route
The classical route for the synthesis of 9-([1,1-biphenyl]-3-yl)-9H-carbazole involves a series of steps that are well-established in the literature.
The classical route typically begins with the synthesis of a biphenyl precursor, such as 1,1-biphenyl-4,4-diol, which is then converted into the target compound through a series of chemical reactions.

The first step in the classical route is the synthesis of 1,1-biphenyl-4,4-diol, which is usually achieved through a condensation reaction between benzaldehyde and acetone in the presence of a base, such as sodium hydroxide.
The resulting biphenyl-4,4-diol is then treated with a strong acid, such as sulfuric acid, to form the bisulfate derivative.

The bisulfate derivative is then treated with sodium hydroxide to convert it into the corresponding sodium sulfate, which is then heated with an organic solvent, such as dichloromethane or chloroform, to remove the sulfuric acid.
The resulting product is then treated with excess triethylamine to form a precipitate, which is then filtered and washed with water to remove the triethylamine hydrochloride salt.

The resulting product is then treated with a base, such as sodium hydroxide, to form a basic salt.
The basic salt is then treated with an organic solvent, such as ethanol, to form a precipitate, which is then filtered and dried to obtain the desired compound.

Modern Route
The modern route for the synthesis of 9-([1,1-biphenyl]-3-yl)-9H-carbazole involves the use of modern synthetic methods and reagents, which can often lead to improved efficiency and reduced cost compared to the classical route.

The modern route typically begins with the synthesis of a phenylboronic acid derivative, such as 4-bromophenylboronic acid, which is then reacted with a diamine, such as 2,2'-diaminopropanamide, in the presence of a catalyst, such as tin(II) chloride, to form the desired compound.

The first step in the modern route is the synthesis of 4-bromophenylboronic acid, which is usually achieved through a bromination reaction of phenylboric acid with hydrogen bromide in the presence of a solvent, such as dichloromethane.
The resulting 4-bromophenylboronic acid is then treated with 2,2'-diaminopropanamide and tin(II) chloride in a solvent, such as N,N-dimethylformamide, to form the desired compound.

Green Route
The green route for the synthesis of 9-([1,1-biphenyl]-3-yl)-9H-carbazole involves the use of environmentally-friendly reagents and conditions, with the aim of reducing the environmental impact of the