シングル・アセチレン・リンクド・ポーフィリン・ナノリング
Michel Rickhaus1, Andreas Vargas Jentzsch1, Lara Tejerina1
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Oxford OX1 3TA, United Kingdom.
Journal of the American Chemical Society
|November 3, 2017
まとめ
研究者はテンプレート誘導ソノガシラ結合を用いてエチン結合のポルフィリンナノリングを合成した. これらの新しいナノリングは,NMRと光スペクトロスコーピーで確認された,非局所化された興奮状態を示します.
科学分野:
- 超分子化学
- 有機合成
- 材料科学
背景:
- ポルフィリンナノリングは複雑なマクロサイクル分子で,様々な分野で応用が可能です.
- ナノリングの形状と電子特性を制御することは 機能性にとって極めて重要です
- テンプレートによる合成は複雑な分子構造を正確に組み立てるための経路を提供します.
研究 の 目的:
- エチン結合のポルフィリンナノリングの合成を 達成するためです
- これらのナノリングの構造特性と 電子移位を調査する.
- 先進的な材料の応用における これらのナノリングの可能性を 探求するためです
主な方法:
- テンプレート指向のソノガシラ結合は,エチン結合のポルフィリンナノリングの合成に使用された.
- 密度関数理論 (DFT) を用いて,低対称性構造を予測した.
- 陽子核磁共鳴 (1H NMR) と光スペクトロスコピーは,溶液中のナノリングの特徴を示すために使用されました.
主要な成果:
- エチンの橋で結ばれた サイクリック・ポルフィリン・ヘクサマーとオクタマーを 合成した.
- DFTの予測は,ポルフィリン単位間の二面曲線による低対称性構造を示した.
- 溶液状態の1H NMRは有効なD6hとD8h対称性を示し,光スペクトルは高度に分散したシングレット興奮状態を示した.
結論:
- エチネ結合のポルフィリンナノリングは,テンプレート誘導ソノガシラ結合によって効果的に合成できます.
- ナノリングは溶液で特定の形状を採用し,興奮状態では有意な電子移位があります.
- これらの発見は,マクロサイクル化学の理解に貢献し,新しい機能的材料への道を開きます.
関連する概念動画
Nomenclature of Alkynes
21.8K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
21.8K
Structure and Physical Properties of Alkynes
13.8K
Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
13.8K
Aromatic Hydrocarbon Anions: Structural Overview
4.0K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
Due to the absence of continuous...
4.0K
Five-Membered Heterocyclic Aromatic Compounds: Overview
5.8K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.8K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
7.7K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.7K


