波形曲二胺:合成,表征和光伏性能
Keisuke Fujimoto1, Seiichiro Izawa2,3,4, Kazuki Yamada1
1Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu, 432-8561, Japan.
ChemPlusChem
|February 8, 2024
概括
新的波形曲烯二氧化物增强了功能性材料的可溶性. 调节分子曲率控制光电转换层形态,提高设备性能.
科学领域:
- 材料科学 材料科学 材料科学
- 有机电子 有机电子
- 超分子化学 超分子化学
背景情况:
- 基于二胺 (PDI) 的材料对于功能应用至关重要.
- 提高溶解度对于加工PDI材料至关重要.
- 曲的分子结构提供了一种提高溶解度的策略,而没有固态障碍.
研究的目的:
- 开发和研究一种新的波形曲烯二氧化物家族.
- 为了比较它们的特性与之前报告的弧形异构体.
- 了解光伏应用的结构-属性关系.
主要方法:
- 合成波形曲的烯二胺化物.
- 形态动力学和聚合行为的表征.
- 电子性能和光伏性能的评估.
- 与弧形二烯二胺化物异构体进行比较分析.
主要成果:
- 与弧形异构体相比,波形曲的PDI表现出增强的刚性和聚合.
- 分子结构,特别是曲率的程度,影响材料形态.
- 异构体之间的光物理和电子接受性质在很大程度上仍然相似.
- 曲率的调制有效地控制光电转换层的形态.
结论:
- 波形曲率是开发高度溶解的PDI材料的可行策略.
- 结构修改影响聚合和薄膜形态,对设备性能至关重要.
- 控制分子曲率为优化基于PDI的有机电子提供了一条途径.
相关概念视频
01:16Structure of Conjugated Dienes
5.2K
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...
5.2K
01:26Photochemical Electrocyclic Reactions: Stereochemistry
1.8K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
1.8K
01:28Stability of Conjugated Dienes
3.4K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
3.4K
01:29UV–Vis Spectroscopy: Woodward–Fieser Rules
24.3K
UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given...
24.3K
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
2.3K
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.
2.3K
01:17Thermal Electrocyclic Reactions: Stereochemistry
2.0K
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.
2.0K