ヘクサチオノコロネン:合成と自己組織化
Long Chen1, Sreenivasa R Puniredd, Yuan-Zhi Tan
1Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
Journal of the American Chemical Society
|October 16, 2012
まとめ
有機半導体の新種であるヘキサチオノコロネン (HTC) は,アルキル鎖の長さに基づいて調節可能な性質を示しています. 関連する化合物よりも強いドナーである一方で,その薄膜トランジスタの性能は,限られた自己組み立てにより,適度なものです.
科学分野:
- オーガニック・エレクトロニクス
- マテリアルサイエンス 材料科学
- 半導体化学 半導体化学について
背景:
- コロネンとチオフェン・アネラド・アナログは,有機半導体の重要な構成要素である.
- 分子構造のチューニングは,電子特性とフィルム形態学の制御に不可欠です.
研究 の 目的:
- 新型ヘクサチオノコロネン (HTC) の合成と特徴づけ.
- HTC相形成と電子特性に対するアルキル鎖の長さの影響を調査する.
- 有機薄膜トランジスタ (OTFT) のHTC性能を評価する.
主な方法:
- ヘキシルとドデシル鎖を持つテトラ置換ヘキサチオノコロネンの合成.
- 段階行動分析のためのX線 difraktionと微分スキャニング熱計.
- 有機薄膜トランジスタ (OTFT) の真空沉積による製造と特徴付け.
主要な成果:
- ヘキサチオノコロネン (HTCs) が成功して合成され,機能化されました.
- 段階形成は,結合したアルキル鎖の長さに強く依存する.
- HTCsは,既存のチオフェンアネラドコロネンと比較して,ドナーの強度が向上していることを示しています.
- 真空に沈着したHTCフィルムは,控えめなフィールド効果の移動性 (0.002cm(2) V(-1) s(-1)).
結論:
- ヘクサチオノコロネンは,調節性特性を有する有機半導体の有望な新種である.
- HTCベースのデバイスの充電輸送を改善するために,フィルム沈着技術のさらなる最適化が必要です.
- 鎖の長さに強い依存は,新しい有機電子材料の合理的な設計のための経路を提供します.
関連する概念動画
02:36Crown Ethers
Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
01:17Thermal Electrocyclic Reactions: Stereochemistry
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
01:18Aromatic Hydrocarbon Cations: Structural Overview
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Removing one hydrogen from the intervening CH2 group with both...
01:16Structure of Conjugated Dienes
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
02:54Coordination Compounds and Nomenclature
In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...