纳二二二胺 (NDTI):合成,结构和应用
Yuta Fukutomi1, Masahiro Nakano, Jian-Yong Hu
1Emergent Molecular Function Research Group, RIKEN Center for Emergent Matter Science (CEMS), Wako, Saitama 351-0198, Japan.
Journal of the American Chemical Society
|July 25, 2013
概括
研究人员合成了纳夫托[2,3-b:6,7-b']二硫二胺化物 (NDTI),是一种多功能有机半导体. 这些NDTI显示出有前途的电子特性,用于开发用于电子应用的新型π功能材料.
科学领域:
- 有机化学 有机化学
- 材料科学 材料科学 材料科学
- 固态物理 固态物理
背景情况:
- 纳[2,3-b:6,7-b']二硫二胺 (NDTI) 是一种有机化合物,在电子设备中具有潜在的应用.
- 开发高效的合成路径和了解NDTI衍生品的电子特性对于其实际使用至关重要.
研究的目的:
- 开发一个简单的合成α,β-非替代和α-化纳夫托[2,3-b:6,7-b']dithiophenediimides (NDTI).
- 为了研究N,N-dioctyl-NDTI的电化学和光学特性.
- 评估NDTI作为新型π功能材料的构建块的潜力.
主要方法:
- 简单的有机合成技术被用于NDTI的准备.
- 进行了电化学研究以确定能量水平 (LUMO,HOMO).
- 光学光谱学被用来分析电子转换和光学特性.
主要成果:
- 实现了α,β-非替代和α-化无毒试验剂的简单合成.
- N,N-dioctyl-NDTI 呈现低的 LUMO 能量水平为 4.0 eV 和一个小的 HOMO-LUMO 间隙约为 2.1 eV.
- 根据分子修饰,NDTI衍生物显示出对n通道,p通道和双极电荷传输的潜力.
结论:
- 通过使用简单的方法,可以有效地合成NDTI.
- 研究的NDTI衍生品具有有利于有机电子的电子和光学特性.
- NDTI是设计具有可调节电子特征的先进π功能材料的有前途和多功能构建块.
相关概念视频
Preparation of Nitriles
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Preparation of 1° Amines: Gabriel Synthesis
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of 1° Amines: Azide Synthesis
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
2° Amines to N-Nitrosamines: Reaction with NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.


