Priyank Kumar Sharma, Akanksha Babbar, Sakshi Sahewal, Soumyajit Das
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引用次数: 0
摘要
环戊烷化多环芳烃(CP-PAHs)因其独特的光电特性和在有机电子设备中的应用而备受关注。菲并蒽(PAP)异构体是很少被研究的 CP-PAHs,迄今为止只有[9,10-e]PAP 异构体被研究过。在此,我们报告了两种 PAP 异构体--7-乙氧基[2,1-e]PAP 1 和 9-乙氧基[1,2-e]PAP 2 的合成、晶体结构和光电特性。这些结构异构体是通过多个步骤合成的,并利用核磁共振、质量和单晶 X 射线衍射分析进行了结构阐释,揭示了异构体的平面骨架。化合物 1 的紫外可见吸收光谱和荧光光谱都比 2 的红移,表明其 HOMO-LUMO 能隙更小,DFT 计算进一步验证了这一点,即 HOMO-LUMO 间距的降低可能是由于 1 的 HOMO 更加不稳定。
Syntheses and Properties of Two Isomeric Phenanthroacephenanthrylene Derivatives
Cyclopenta-annulated polycyclic aromatic hydrocarbons (CP-PAHs) are of significant interest due to their unique optoelectronic properties and applications in organic electronic devices. Phenanthroacephenanthrylene (PAP) isomers are CP-PAHs that have been rarely investigated, and only the [9,10-e]PAP isomer was explored to date. Herein, we report the syntheses, crystal structure and optoelectronic properties of two PAP isomers, 7-ethoxy[2,1-e]PAP 1 and 9-ethoxy[1,2-e]PAP 2. The structural isomers were synthesized in multi-steps, and structural elucidations were performed using NMR, mass, and single-crystal X-ray diffraction analyses, revealing planar backbone of the isomers. UV-visible absorption and fluorescence spectra of compound 1 were red-shifted than that of 2, suggesting smaller HOMO–LUMO energy gap which is further validated by DFT calculations that suggested the lowering of HOMO–LUMO spacing could be attributed to the greater destabilization of HOMO for 1.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.