Fine-Tuning the Electronic Properties of Azo Chromophore-Incorporated Perylene Bisimide Dyads.,The Journal of Organic Chemistry

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Fine-Tuning the Electronic Properties of Azo Chromophore-Incorporated Perylene Bisimide Dyads.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-07-23 , DOI: 10.1021/acs.joc.0c01166
Tankut Türel ₁ , Suresh Valiyaveettil ₁

Affiliation

Perylene bisimide (PBI) and azo-compounds are fascinating molecules with interesting optical properties. Here, we combine the two chromophores to prepare nonconjugated and conjugated stable azo-PBI dyes. The detailed structural characterization, comparison of properties, and solid-state self-assembly of the compounds are discussed. The incorporation of azo groups at the bay side of PBI led to significant changes in optical properties as compared to the model PBIs (M₁ and M₂). All new azo-PBIs showed photoinduced isomerization, which caused disaggregation and enhancement in fluorescence. The amine-incorporated azo-PBIs (3 and 6) reduced chloroauric acid into gold nanoparticles. The current study offers a simple synthetic strategy and comparison of the properties of conjugated and nonconjugated azo-PBIs, which could be useful in photoelectronic devices.

中文翻译：

微调含偶氮发色团的Per双酰亚胺二元化合物的电子性质。

ylene双酰亚胺（PBI）和偶氮化合物是具有有趣光学特性的引人入胜的分子。在这里，我们结合两个生色团，以制备非共轭和共轭的稳定偶氮PBI染料。讨论了化合物的详细结构表征，性质比较和固态自组装。与模型PBI（M ₁和M ₂）相比，在PBI的海湾一侧引入偶氮基团导致光学性能发生重大变化。所有新的偶氮-PBI均显示出光诱导的异构化，这引起了分解和荧光增强。结合有胺的偶氮PBI（3和6）将氯金酸还原成金纳米颗粒。当前的研究提供了一种简单的合成策略，并比较了共轭和非共轭偶氮PBI的性质，这可能在光电器件中有用。

更新日期：2020-08-21

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