合成13,14-二取代二並苯[b,j][4,7]菲啶作為研究π-π作用力的平臺;Synthesis of 13,14-disubstituted dibenzo[b,j][4,7]phenanthroline as the platform to study π-π interaction

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题名:	合成13,14-二取代二並苯[b,j][4,7]菲啶作為研究π-π作用力的平臺;Synthesis of 13,14-disubstituted dibenzo[b,j][4,7]phenanthroline as the platform to study π-π interaction
作者:	盧彥丞;Lu-Yen-Cheng
贡献者:	化學學系
关键词:	π-π作用力;π-π interaction
日期:	2023-07-27
上传时间:	2024-09-19 14:46:12 (UTC+8)
出版者:	國立中央大學
摘要:	本論文之研究方向為將1,4-環己二酮與鄰位胺基之苯酮透過Friedländer縮和反應，一步建構出13,14號位 (躺椅區)雙取代 dibenzo [b,j][4,7] phenanthroline。在此系列中，我們提供了兩個取代基在擁擠環境中的新的立體參數 (不同於A value或B value)；而當取代基均為苯環系統時，我們可以初步探討π-π 作用力是如何影響分子動力學及構型分佈。本論文探討的方式為以下三種 (1) 我們透過變溫NMR來進行實驗，透過尋找崩潰溫度，再將所得之參數代入艾林方程式 (Erying equation) 中，便可探討不同取代基對於苯環旋轉能障以及消旋能障的影響；(2) 我們也透過分析分子間不同旋轉異構物 (rotamers) 的比例來探討π-π作用力影響之下的結果；(3) 分析晶體結構有助於我們了解分子的基態構型。本研究中的合成策略相對簡單、官能基耐受性高且產率大多為中上。在研究方面則可提供多元的探討，這不禁令人期待後續的研究潛力。 ;The focus of this study is to synthesize 13,14-disubstituted dibenzo[b,j][4,7]phenanthroline by utilizing the Friedländer condensation reaction between 1,4-cyclohexanedione and ortho-aminoketone. This one-step synthesis provides a platform to investigate the steric hindrance of two substituents in a crowded environment. When both substituents are phenyl ring, the parallel offset arrangement can be utilized to explore how π-π interaction can affect intramolecular dynamic and conformer distributions. In this study, three approaches were employed: (1) Variable Temperature NMR experiments were conducted to determine the coalescence temperature temperature of the synthesized compound. These temperatures were then put in Erying equation to assess the activation energy of aryl rotation and racemization barrier. Moreover, substituent effect on these motions can also be evaluated. (2) The proportions of different rotamers were analyzed to investigate the influence of π-π interaction. (3) Analysis of crystal structures helps us realize the ground state conformation of the molecules. The synthetic strategy in this study was relatively straightforward and adaptable, with mostly moderate to high yields. The research direction highlights the versatility of this platform for diverse investigations. Its potential for future applications were highly anticipated.
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