芴[1,9-kl]茚并[1,2,3-de]四苯之衍生物合成方法以在先前實驗室的研究中提出，例如化合物1。由於此種衍生物經過測試在電子元件上具有良好的導電性，我們將嘗試將此類衍生物之π-系統結構進行修飾進而分析對性質的影響。
本篇論文主要是觀察不同π-系統結構改變對分子HOMO-LUMO能階差之關聯，因此我們嘗試去合成在π-系統添加氟官能基之化合物如5和9，還有π-系統延伸之化合物如21。我們利用先前實驗室提出的合成步驟合成出化合物5，然而化合物9和21經過許多嘗試後仍未找出合適的反應途徑。
藉由分析邊側π-系統添加氟官能基之化合物5與化合物1作比較我們得到兩者HOMO-LUMO能階差區別不大，而未來也會繼續找尋合適的反應途徑完成化合物9與21之合成，讓我們能夠了解更多π-系統變化與HOMO-LUMO能階差之趨勢。

Our laboratory has synthesized a series of fluoreno[1,9-kl] indeno[1,2,3-de]tetraphene derivatives, such as compound 1. Due to its good performance in electronic devices, we will attempt to modify its structure and analyze the properties of its homologues.
This work aims to investigate the correlation between the π-system and HOMO-LUMO gap. We attempted to synthesize the compounds bearing fluorine functional groups, such as compounds 5 and 9. Furthermore, a π-system extended compound, such as compound 21, is also included in this study. Based on our laboratory`s previous work, we successfully synthesized compound 5. However, the synthesis of compounds 9 and 21 was unsuccessful. Although various methods were tested, we were unable to obtain the final compounds.
Here, we analyze the properties of compound 5 in comparison with compound 1 to examine the effects of π-system modification. The results indicate that there is little difference between them. Meanwhile, alternative synthetic routes may be explored in the future to obtain final products such as compounds 9 and 21, enabling further discussion pf this class of structures.

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