Internally diketopyrrolopyrrole-bridged bis-anthracene macrocycle: a multifunctional fluorescent platform†

IF 7.6 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Huan Zhou, Yuxuan Zhang, Zhiye Zheng, Junhua Wan, Hui Zhang, Kunhua Lin, Jonathan L. Sessler and Hongyu Wang
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Abstract

A covalently bridged macrocycle (5) comprising two anthracene strands connected at the lactam positions of a diketopyrrolopyrrole (DPP) chromophore has been constructed. The crystal structure reveals that the central DPP chromophore is wrapped with the externally twisted bis-anthracene macrocycle. The internally bridged macrocycle architecture endows 5 with multifunctional properties. Due to shielding by the double anthracene straps, 5a and a polymer derived from it, DPP-Cycle, display strong fluorescence emission features in both organic media and the solid state. Moreover, the emission colors of these macrocyclic materials can be effectively tuned through external stimuli such as mechanical and thermal treatments, as well as solvent fuming. Compound 5a is stable in the presence of most metal cations but degrades rapidly when it comes in contact with Cu2+ in acetonitrile. This decomposition, which is thought to involve a reaction at the central DPP via a radical-mediated mechanism, was found to be accelerated in 5a compared to the non-cyclic analogue 2a. This leads us to suggest that internally bridged macrocycles, such as those described here, may have a role to play as fluorescent Cu2+ sensors. Finally, the high fluorescence of 5a in the solid state enables its use in the area of latent fingerprint (LFP) imaging.

Abstract Image

内二酮吡咯-吡咯桥接双蒽大环:一种多功能荧光平台
一个共价桥接的大环结构(5),包括在二酮吡咯(DPP)发色团的内酰胺位置连接的两条蒽链。晶体结构表明,DPP中心的生色团被外部扭曲的双蒽大环包裹。内部桥接的大循环架构赋予5多功能的特性。由于双蒽带的屏蔽作用,5a及其衍生的聚合物DPP-Cycle在有机介质和固态中都表现出很强的荧光发射特性。此外,这些大环材料的发射颜色可以通过外部刺激,如机械和热处理,以及溶剂发烟有效地调节。化合物5a在大多数金属阳离子存在下是稳定的,但在乙腈中与Cu2+接触时降解迅速。这种分解被认为是通过自由基介导的机制参与了中央DPP的反应,与非循环类似物2a相比,在5a中发现了加速。这使我们认为,内部桥接的大环,如这里描述的,可能具有荧光Cu2+传感器的作用。最后,固体状态下5a的高荧光允许其用于潜在指纹(LFP)成像区域。
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来源期刊
Chemical Science
Chemical Science CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
14.40
自引率
4.80%
发文量
1352
审稿时长
2.1 months
期刊介绍: Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.
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