盤狀分子引入單一具偶極鹵素原子對其液晶態分子緊密堆疊的影響

Effect of packing pattern in discotic Molecules by incorporating mono halogenated analogs

陳永清(Yung-Ching Chen)

指導教授 ： 徐秀福

淡江大學/理學院/化學學系碩士班/碩士(2013年)

https://doi.org/10.6846/TKU.2013.00626

摘要

系列一第一部份以六炔苯基苯為中心核，在其中一側臂分別引入鄰氟苯、間氟苯及對氟苯，期望藉由引入氟原子的位置不同，分子在排列時有立體障礙及分子偶極方向的差異，而形成不同型式的排列。結果引入不同位置的單一氟原子於六炔苯基苯之化合物，皆不具液晶性質。第二部分，將對位的單一氟原子改變成溴及氯原子;因引入不同的鹵素原子，可影響分子的偶極矩，藉由極矩大小的不同，調整或改變其液晶的性質。並成功只引入單一鹵素原子，便將原為向列型的液晶分子，改變為具有高秩序性的筒型液晶分子。
系列二以六苯并蔻為中心核，在六苯并蔻最外環的1, 3, 5環引入氟原子，而於2, 4, 6環的位置上引入接正戊烷末端鏈之苯環。期望藉著分子間氟原子的斥力，使分子錯開一小角度堆疊，讓盤與盤之間更緊密排列，並增加中心核的接觸面積，以提高在光電裝置中筒內單位面積的電流密度。此外，以C3對稱的方式降低分子的對稱性，可使溶解度提升並降低其澄清點。目前只成功合成六苯基苯衍生物

關鍵字

六炔苯基苯 ； 六苯并蔻 ； 盤狀分子 ； 筒型液晶 ； 單一鹵素原子

並列摘要

The first part of series one is make use of hexakis(phenylethynyl)benzene derivatives as the central core, and introduced o-fluorophenyl, m-fluorophenyl, p-fluorophenyl as one of side arm, respectively. Expectations by introducing fluorine atoms in different positions can make molecules arrange due to steric effect and differ in dipole orientation to become different types of arrangement. The results of the introduction of a single fluorine atom different locations in hexakis(phenylethynyl)benzene derivatives, neither liquid crystal. The second part replaced the para position of monofluorine atom to chlorine and bromine. Because introducing different halogen atoms, can affect the molecular dipole moment. The properties of the liquid crystal can be adjusted and changed with different moment. And the successful introduction of only one halogen atom, alter nematic liquid crystal molecules to a high order of the columnar liquid crystal molecules.
In series two, a compound which introducd fluorine atom onto 1, 3, 5 position and the benzene jointed terminal pentane onto 2, 4, 6 position of hexabenzocoronene central core as the target product. It’s anticipated that the repulsion of fluorine atoms between molecules twisted the whole molecules. Therefore, the distances between disc-disc arranged closer and increased the contact area of the central core, for the purpose of raising current density in the columns of the photovoltaic devices. In addition, C3 symmetry enhanced solubility and reduced its clearing point. However, only the precursor, hexaphenylbenzene derivatives, was successfully synthesized.

並列關鍵字

hexakis(phenylethynyl)benzene ； discotic ； mono halogenated analogs ； columnar liquid crystal ； hexabenzocoronene

參考文獻

(1) Reinitzer, F. Monatsh. Chem. 1888, 9, 421.

(2) Lehmann, O. Z. Phys. Chem. 1889, 4, 462.

(5) Chen, H.-H.; Lin, H.-A.; Chien, S.-C.; Wang, T.-H.; Hsu, H.-F.; Shih, T.-L.; Wu, C. J. Mater. Chem. 2012, 22, 12718.

(6) Lee, S.-L.; Lin, H.-A.; Lin, Y.-H.; Chen, H.-H.; Liao, C.-T.; Lin, T.-L.; Chu, Y.-C.; Hsu, H.-F.; Chen, C.-h.; Lee, J.-J.; Hung, W.-Y.; Liu, Q.-Y.; Wu, C. Chem. Eur. J. 2011, 17, 792.

(13) Kikuzawa, Y.; Mori, T.; Takeuchi, H. Org. Lett. 2007, 9, 4817.