5,14-Diaryldiindeno[2,1-f:1',2' -j]picene:一种具有部分二基性质的新型稳定 [7]烯
Ya-Chu Hsieh1, Cheng-Feng Wu1, Yi-Ting Chen
1Department of Chemistry , National Cheng Kung University , 70101 Tainan , Taiwan.
Journal of the American Chemical Society
|October 23, 2018
概括
研究人员合成了一种稳定的螺旋,5,14-Diaryldiindeno[2,1-f:1
科学领域:
- 有机化学
- 材料科学
- 超分子化学
背景情况:
- 螺旋是具有独特结构和电子性质的复杂有机分子.
- 开发热和化学稳定的螺旋化合物对于先进的应用至关重要.
研究的目的:
- 合成和表征一种新的螺旋性烯,5,14-Diaryldiindeno[2,1-f:1',2' -j]picene (DDP).
- 研究DDP及其衍生物的结构,热和电子特性.
主要方法:
- 从1,4-bis[2-烯]开始进行多步骤的有机合成.
- 用于螺旋脊柱的结构验证的X射线晶体学.
- 用于性能评估的光谱技术 (ESR,UV-Vis-NIR) 和设备制造.
主要成果:
- 在四个步骤中成功合成DDP.
- X射线结晶学证实了螺旋结构的高分离障碍 (> 50 kcal/mol).
- DDP衍生品具有小的HOMO-LUMO间隙 (1.31 eV),ESR活性和从UV到NIR的广泛光吸收.
- 在溶液处理的有机场效应晶体管中证明了双极电荷传输.
结论:
- 5,14-Diaryldiindeno[2,1-f:1',2' -j]picene是一种热和化学稳定的螺旋烯,具有有前途的光电子特性.
- 这种独特的螺旋结构有助于实现高种族化障碍和多功能性.
- DDP是有机电子和光学新型材料.
相关概念视频
Nomenclature of Alkynes
18.3K
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:
18.3K
Structure of Conjugated Dienes
5.5K
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...
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...
5.5K
Diels–Alder Reaction: Characteristics of Dienes
3.7K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
3.7K
Aromatic Hydrocarbon Anions: Structural Overview
3.5K
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...
3.5K
Stability 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
UV–Vis Spectroscopy: Woodward–Fieser Rules
30.7K
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...
30.7K


