Synthesis, structures and properties of two donor-acceptor acridone-based compounds.

IF 0.7 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Acta Crystallographica Section C Structural Chemistry Pub Date : 2023-10-01 Epub Date: 2023-09-21 DOI:10.1107/S2053229623007994

Ziqiang Chen, Gaojie Xin, Penglian Gao, Yingying Jin

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引用次数: 0

Abstract

Two donor-acceptor acridone-based compounds, namely, 2-{10-[4-(diphenylamino)phenyl]acridin-9-ylidene}malononitrile (TPA-AD-DCN), C₃₄H₂₂N₄, and 2-{10-[4-(9H-carbazol-9-yl)phenyl]acridin-9-ylidene}malononitrile (CzPh-AD-DCN), C₃₄H₂₀N₄, have been synthesized in high yield and their structures determined. TPA-AD-DCN and CzPh-AD-DCN crystallized in the centrosymmetric space groups P-1 and P2₁/c, respectively. Both molecules adopt a `butterfly-like' configuration of the common part of the structure and differences occur within the substituents on the acridine N atom. A Hirshfeld surface analysis showed that the H...H and C...H/H...C contacts constitute a high percentage of the intermolecular interactions. The optical and electrochemical properties, as well as theoretical calculations, of TPA-AD-DCN and CzPh-AD-DCN support the structural characterization of these materials. As crystallization-induced emission materials, TPA-AD-DCN and CzPh-AD-DCN are anticipated to be of potential use in the construction of promising optoelectronic materials.

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两种给受体吖啶酮基化合物的合成、结构和性能。

以高产率合成了两种基于给受体吖啶酮的化合物，即2-{10-[4-（二苯基氨基）苯基]吖啶-9-亚基}丙二腈（TPA-AD-DCN），C34H22N4和2-{10-[4-（9H-咔唑-9-基）苯基]阿啶-9-亚基}丙二腈（CzPh-AD-DCN），C34 H20N4，并测定了它们的结构。TPA-AD-DCN和CzPh AD DCN分别在中心对称空间群P-1和P21/c中结晶。这两种分子在结构的共同部分都采用“蝴蝶状”构型，并且在吖啶N原子上的取代基内出现差异。Hirshfeld表面分析表明，H…H和C…H/H…C接触在分子间相互作用中占很大比例。TPA-AD-DCN和CzPh AD-DCN的光学和电化学性质以及理论计算支持了这些材料的结构表征。TPA-AD-DCN和CzPh AD-DCN作为结晶诱导发射材料，有望在构建有前景的光电子材料中发挥潜在的作用。

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来源期刊

Acta Crystallographica Section C Structural Chemistry CHEMISTRY, MULTIDISCIPLINARYCRYSTALLOGRAPH-CRYSTALLOGRAPHY

CiteScore

1.60

自引率

12.50%

发文量

148

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.