New organic semiconductors with imide/amide-containing molecular systems

Zitong Liu1, Guanxin Zhang, Zhengxu Cai

  • 1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic SolidsInstitute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.

Summary

High-performance organic semiconductors using imide/amide frameworks show promise for advanced electronics. Research highlights recent progress in these materials for high-mobility field-effect transistors.

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Preparation of Amides01:29

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

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Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
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Amines to Amides: Acylation of Amines01:19

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Amines: Introduction01:07

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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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