Analysis of Solid-State Emission of the p-Bis(2,2-dicyanovinyl)benzene Analogue through Combined X-ray, Synchrotron, and Microcrystal Electron Diffraction,Crystal Growth & Design

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Analysis of Solid-State Emission of the p-Bis(2,2-dicyanovinyl)benzene Analogue through Combined X-ray, Synchrotron, and Microcrystal Electron Diffraction
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2024-08-23 , DOI: 10.1021/acs.cgd.4c00856
Poonam Deka ₁ , Shilpi Jaiswal ₂ , Parishmita Sarma ₁ , Debajit Bora ₃ , Takanori Nakane _{4,

5} , Akihiro Kawamoto _{4,

5} , Yusuke Ohnishi ₄ , Genji Kurisu _{4,

5} , Sanjeev Pran Mahanta ₃ , Khaled Althubeiti ₆ , Kouhei Ichiyanagi ₇ , Toshiyuki Sasaki ₇ , Ranjit Thakuria ₁

Affiliation

Organic solid-state emissive materials have recently gained significant attention for their optoelectronic properties, leading to the design of various optical devices and sensors. Achieving highly efficient solid-state fluorescence is challenging. Moreover, understanding a structure–property relationship is crucial for designing and improvising solid-state emitters. Herein, we have synthesized different compounds having p-bis(2,2-dicyanovinyl)benzene as a core structure and varied the substitution position and linker length. However, after several batches of failed crystallization for a few analogues, microcrystal electron diffraction (MicroED) and synchrotron were used for structure elucidation that helps in better understanding the solid-state emission behavior of the synthesized organic fluorophores. During the analysis, MicroED helps us to characterize a novel polymorph of 4,4′-biphenyldicarboxaldehyde (starting material for BP-1 and BP-2) and an intermediate product of BP-2, i.e., monoaldehyde derivative, from a powdered mixture. Based on the structural analysis, it was observed that π–π interactions and C–H···O/N interactions play a dominant role in tuning the photophysical properties of these organic fluorophores.

中文翻译：

通过组合 X 射线、同步加速器和微晶电子衍射分析对双 (2,2-二氰基乙烯基) 苯类似物的固态发射

有机固态发射材料最近因其光电特性而受到极大关注，从而导致了各种光学器件和传感器的设计。实现高效固态荧光具有挑战性。此外，理解结构-性能关系对于设计和临时制作固态发射器至关重要。在此，我们合成了以对双(2,2-二氰基乙烯基)苯为核心结构并改变取代位置和连接基长度的不同化合物。然而，在一些类似物的几批结晶失败后，微晶电子衍射（MicroED）和同步加速器被用于结构阐明，这有助于更好地理解合成的有机荧光团的固态发射行为。在分析过程中，MicroED 帮助我们从粉末混合物中表征了 4,4'-联苯二甲醛（ BP-1和BP-2的起始材料）的新型多晶型物以及BP-2的中间产物，即一醛衍生物。基于结构分析，观察到π-π相互作用和C-H·O/N相互作用在调节这些有机荧光团的光物理性质中起主导作用。

更新日期：2024-08-23

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