ペンダントチオフェンの酸化サイクル化による機能化可能なポリサイクルアロマティック
John D Tovar1, Aimee Rose, Timothy M Swager
1Department of Chemistry, Center for Materials Science and Engineering, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Journal of the American Chemical Society
|June 27, 2002
まとめ
研究者らは,鉄 (III) クロリドを用いて硫黄を含む多循環性アロマティックを大量に合成する方法を開発した. この戦略はサイクル化を制御し,ポリマー形成を防止し,ポリマーの性質を研究するためのさらなる機能化を可能にします.
科学分野:
- 有機化学 オーガニック・ケミストリー
- ポリマーサイエンスの科学
- マテリアルサイエンス 材料科学
背景:
- ポリサイクル芳香炭化水素 (PAH) は,材料科学において極めて重要です.
- アロマティック前駆物のポリメリゼーションを制御することは,依然として課題です.
- チエニルを含む前駆体は,PAH合成にユニークな反応性を提供します.
研究 の 目的:
- 大量の硫黄を含むポリサイクル芳香剤を合成するための一般的な戦略を策定する.
- ポリマーの光物理学的特性に対する構造的剛性の影響を調査する.
- チエニルベースのポリマーのサイクリングとポリメリゼーション経路を探求する.
主な方法:
- チエニル前駆物の酸化循環は鉄 (III) クロライド媒介による.
- ポリマー形成を抑制するために,酸化中介物の制御されたサイクリング.
- ハロゲン化と合成アロマティックコアの機能化.
- アリレン-エチニレンポリマーの合成と光物理学的特徴付け.
主要な成果:
- 大量の硫黄を含むPAHの合成のための一般的な戦略が確立されました.
- コントロールされたサイクリング経路が達成され,ポリマー形成を最小限に抑えました.
- 合成されたポリマーは,染色体硬度に基づく調節可能な光物理的性質を示した.
- 刺激状態の寿命が長くなることは,固い,芳香化された染色体で観察されました.
結論:
- チエニル前駆体の酸化サイクル化は,複雑なPAHへの多用途な経路を提供します.
- 剛性に対する合成制御は,ポリマーの光物理的振る舞いに大きく影響する.
- この研究は,結合ポリマーの構造-性質関係に関する洞察を提供します.
関連する概念動画
Introduction to Functional Groups
Functional groups are group of atoms with specific chemical properties that occur within organic molecules and sometimes denoted as “R”. Functional groups are found along the carbon backbone of macromolecules can form chains or rings of carbon atoms. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of common functional groups
The table below summarizes some of the major functional groups in organic chemistry. (The...
Preparation of Epoxides
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Properties of Organometallic Compounds
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
Aromatic Compounds: Overview
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
In 1825, Faraday isolated benzene...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Radical Autoxidation
The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...


