扭转对交叉共轭噻吩并[3,4-b]噻吩光色团的影响

IF 1.9 4区 化学 Q2 CHEMISTRY, ORGANIC
Nicholas P. Adams, John D. Tovar
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引用次数: 0

摘要

光致共振共轭聚合物是现代有机电子学的一个前景广阔的目标。人们在聚合物结构中以共价方式加入了许多光开关重复单元,以实现响应性色材料,最常见的方式是通过侧链附属物或沿着 π 共轭主链进行正式共轭。我们最近披露了一种新设计,即光电开关元件与共轭聚合物主链交叉共轭。在这种情况下,我们发现光电转换的程度部分取决于主链的竞争性光吸收,而通过使用携带大部分前沿分子轨道密度的光开关图案,可以抑制这种竞争性光吸收。在此,我们报告了一系列基于噻吩并[3,4-b]噻吩(TT)的光致变色剂的建模和合成,这些光致变色剂具有不同的芳香侧翼,赋予了不同程度的立体体积和π-共轭,从而阐明了立体因素和电子因素之间的平衡作用,以促进光致变色。通过这些模型系统,我们可以更好地了解扩展低聚物和聚合物 π 共轭材料中光致变色单元的行为。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Torsional influences on cross‐conjugated thieno[3,4‐b]thiophene photochromes
Photoresponsive conjugated polymers are a promising target for modern organic electronics. Numerous photoswitchable repeat units have been included covalently within polymeric structures to enable responsive chromic materials, most commonly through side‐chain appendages or through formal conjugation along a π‐conjugated backbone. We recently disclosed a new design whereby the photoswitch elements are cross conjugated to a conjugated polymer main chain. In this case, we found that the extent of photoconversion was dictated in part by competitive main chain light absorption, which could be suppressed by using a photoswitching motif that carried most of the frontier molecular orbital densities. Here, we report the modeling and synthesis of a series of thieno[3,4‐b]thiophene (TT)‐based photochromes with various aromatic flankers imparting varying degrees of steric bulk and π‐conjugation in order to elucidate the balancing act between steric and electronic factors to promote photochromism. These model systems provide a better understanding of the behavior of photochromic units within extended oligomeric and polymeric π‐conjugated materials.
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来源期刊
CiteScore
3.60
自引率
11.10%
发文量
161
审稿时长
2.3 months
期刊介绍: The Journal of Physical Organic Chemistry is the foremost international journal devoted to the relationship between molecular structure and chemical reactivity in organic systems. It publishes Research Articles, Reviews and Mini Reviews based on research striving to understand the principles governing chemical structures in relation to activity and transformation with physical and mathematical rigor, using results derived from experimental and computational methods. Physical Organic Chemistry is a central and fundamental field with multiple applications in fields such as molecular recognition, supramolecular chemistry, catalysis, photochemistry, biological and material sciences, nanotechnology and surface science.
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