アミノフェナレニル基の中性急端分子導体の新しいファミリー:合成,構造,固体状態特性
Swadhin K Mandal1, Mikhail E Itkis, Xiaoliu Chi
1Department of Chemistry, University of California, Riverside, California 92521-0403, USA.
Journal of the American Chemical Society
|June 2, 2005
まとめ
研究者らは,新しいスピロビス (1,9-ダイアミノ-置換-フェナレニル) ボロン中性基を開発した. これらの化合物は高い電気伝導性を示し,有機電子のアプリケーションに有望です.
科学分野:
- マテリアルサイエンス 材料科学
- 有機化学 オーガニック・ケミストリー
- 固体物理 固体物理学
背景:
- 中性有機ラジカルは,電子アプリケーションに興味があります.
- スパイロリンクされた分子構造は,ユニークな構造特性を有しています.
研究 の 目的:
- スパイロビス-1,9-ダイアミノ-置換-フェナレニル) ボロン中性基の新しいファミリーを合成し,特徴づけること.
- 結晶構造と電気伝導性を含む,これらの新種のラジカルの固体性質を調査する.
主な方法:
- 構造分析のための単結晶X線 difraktion. 構造分析のための単結晶X線 difraktion.
- ラジカル特性を確認するために,磁気感受性の測定を行います.
- 室温での電気伝導度測定. 室温での電気伝導度測定.
主要な成果:
- 3つの新しいスピロビス (1,9-ダイアミノ-置換-フェナレニル) ボロンの中性基の準備と結晶化が成功しました.
- 構造分析により,有意な分子間接触のないモノメリック単位が明らかになった.
- 磁気測定により,分子あたり1つのペアレススピンの存在が確認されました.
- 2つの化合物は,高い室温伝導率 (最大4×10−2 S/cm) を示し,それらを高度に伝導性のある中性有機固体として分類しました.
結論:
- 新しいスパイロボロンラジカルは,高伝導性の有機物質の新種のクラスを表しています.
- 電気伝導性は,狭い帯域幅にもかかわらず,分子間接触と計算された帯域分散と相関しています.
- これらの発見は,先進的な有機電子材料の設計のための道を開く.
関連する概念動画
01:16Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
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.
01:28Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
01:19Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
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.
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.
01:23Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
01:07Amines: Introduction
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.