將多炔化合物炔轉烯之衍生物的合成及發光性質研究

Synthesis and Luminescent Property Investigation of Yne-Ene Conversion Derivatives of Multi-Alkyne Compounds

黃俊祺(Chun-Chi Huang)

指導教授 ： 徐秀福

淡江大學/理學院/化學學系碩士班/碩士(2021年)

https://doi.org/10.6846/TKU.2021.00755

摘要

隨著科技的進步，對於偵測器的要求就越高，科學家們致力於研發高敏感及有高選擇性的系統。由於聚集誘導發光(AIE)材料有別於一般有機化合物，它可以在高濃度溶液或固體時放出螢光，在工業發展、環境偵測及生物系統等領域發揮重要作用。
自2001年唐本忠博士團隊發現AIE現象至今已經20年，小的AIE分子骨架已幾乎開發完畢，現在大部分作法是將AIE小分子修飾到目標化合物上，使其具有AIE的性質，卻很少人尋找新的AIE分子骨架。因此，本論文為了開發新的分子骨架，預計將多炔化合物進行修飾，將其三鍵反應成雙鍵，並導入兩個芳基，增加分子內的立體阻礙，研究其聚集發光性質。

關鍵字

聚集誘導發光 ； 螢光 ； 多炔化合物 ； 修飾 ； 立體阻礙

並列摘要

With the advancement of science and technology, scientists have been committed to the development of more sensitive and selective sensing systems. In contrary to most organic fluorescent materials in which emission was quenched upon aggregation, aggregation-induced emission (AIE) materials emit fluorescence in high-concentration solutions or solids to play an important role in industrial development, environmental detection, and biological systems.
Since Dr. Tang, B. Z.’s team discovered the AIE phenomenon has been 20 years. Small molecular AIE skeletons have been developed studied in details and only a few molecular skeletons have been found to exhibit AIE behaviors. Currently, most AIE materials are derived from these few AIE molecular skeleton. In this thesis, new materials though yne-ene conversion and addition of two aryls of some multi-alkyne compounds to increase the steric hindrance were synthesized and their luminescent properties upon aggregation were studied.

並列關鍵字

aggregation-induced emission ； luminescence ； multi-alkyne compounds ； derivatives ； steric hindrance

參考文獻

1 A. J. Samson; A. O. John Excimers and Exciplexes of Conjugated Polymers. Science 1994, 265, 765−768.

2 X. F. Ma; R. Sun; J. H. Cheng; J. Y. Liu; F. Gou; H. F. Xiang; X. G. Zhou Fluorescence Aggregation-Caused Quenching versus Aggregation-Induced Emission: A Visual Teaching Technology for Undergraduate Chemistry Students. J. Chem. Educ. 2016, 93, 345−350.

3 H. Wang; E. G. Zhao; W. Y. Lam; B. Z. Tang AIE luminogens: emission brightened by aggregation. Mater. Today Commun. 2015, 18, 365−377.

4 J. Luo; Z. Xie; J. W. Lam; L. Cheng; H. Chen; C. Qiu; H. S. Kwok; X. Zhan; Y. Liu; D. Zhu; B. Z. Tang Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole. Chem. Commun. 2001, 18, 1740−1741.

5 L. C. Leung; N. Xie; W. Z. Yuan; Y. Liu; Q. Y. Wu; Q. Peng; Q. Miao; W. Y. Lam; B. Z. Tang Restriction of Intramolecular Motions: The General Mechanism behind Aggregation-Induced Emission. Chem. Eur. J. 2014, 20, 1−6.