Synthesis and Properties of Alkoxy-Bridged Triphenylene and Perylene Monoimide Diesters Dyads

doi:10.6023/cjoc201512048

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (6): 1325-1334.DOI: 10.6023/cjoc201512048 Previous Articles Next Articles

Articles

烷氧基桥接的苯并菲和苝单亚胺二酯二元化合物的合成及性质研究

孔翔飞^a, 刘鹏^a, 王桂霞^a, 夏励婷^a, 戴胜平^a, 苏剑^a, 廖培海^a, 刘峥^a, 穆林平^b

a 桂林理工大学化学与生物工程学院桂林 541004;
b 山西师范大学物理与信息工程学院临汾 041004

收稿日期:2015-12-30 修回日期:2016-01-22 发布日期:2016-02-24
通讯作者: 王桂霞, 穆林平 E-mail:2010033@glut.edu.cn;mulinping6266@163.com
基金资助:
国家自然科学基金(Nos.11364013,21266006)、广西教育厅(No.KY2015YB129)和桂林理工大学博士启动基金资助项目.

Synthesis and Properties of Alkoxy-Bridged Triphenylene and Perylene Monoimide Diesters Dyads

Kong Xiangfei^a, Liu Peng^a, Wang Guixia^a, Xia Liting^a, Dai Shengping^a, Su Jian^a, Liao Peihai^a, Liu Zheng^a, Mu Linping^b

aCollege of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004;
b School of Physics and Information Engineering, Shanxi Normal University, Linfen 041004

Received:2015-12-30 Revised:2016-01-22 Published:2016-02-24
Supported by:
Project supported by the National Natural Science Fondation of China (Nos. 11364013, 21266006), the Education Department of Guangxi Province (No. KY2015YB129) and the Startup Foundation for Doctor of Guilin University of Technology.

1. Synthesis and Properties of Alkoxy-Bridged Triphenylene and Perylene Monoimide Diesters Dyads.PDF(490KB)

Abstract

Columnar discotic liquid crystals have high charge carrier mobility, and donor-bridge-accepter-based supra-mole- cular compounds have photoinduced intramolecular electron transfer behavior. In order to make the organic materials possess these two performances, dyads composed of hexaalkoxy triphenylene unit and perylene monoimide diesters unit were prepared in this work. In the dyads, the flexible alkoxys were used as bridges, the triphenylene units having six electron-donating alkoxy tails acted as electron donors, and the perylene monoimide diesters units having four electron-withdrawing carbonyls acted as electron acceptors. Their structures were established by proton nuclear magnetic resonance (¹H NMR), infrared spectroscopy (IR), mass spectrometry (MS) and elemental analysis (EA). The photophysical properties were characterized by means of UV-Vis absorption spectroscopy and fluorescence spectroscopy. The results showed that in dilute dichloromethane solutions the absorbance strength of these dyads was the sum of that of their monomers, hexakishexyloxy triphenylene (HAT6) and N-hexyl-perylene monoimide dihexyl esters (PMD6), and not interfered by the length of flexible bridges. When excited at 475 nm, the strength of the fluorescence of the dyads decreased when the spacers shortened from dodecyloxy, decyloxy, hexyloxy to ethoxy groups. Actually, when the spacer was ethoxy group, the fluorescence of the dyad was almost quenched completely. This is attributed to the photoinduced electron transfer properties (PET) between the donor and acceptor units. When excited at 280 nm, the strength of the fluorescence of the triphenylene units also became weaker when the spacers shortened from dodecyloxy to ethanyloxy. At the same time, the strength of the fluorescence of the perylene units became stronger. This is attributed to energy transfer from the triphenylene unit to the perylene unit. In addition, their liquid crystalline properties have been studied by polarized optical microscopy (POM) and differential scanning calorimetry (DSC). The results demonstrated that when the spacers were decyloxy and dodecyloxy the dyads possessed columnar liquid crystal behavior in the heating circle, while in the cooling circle only the dyad bearing the dodecyloxy spacer showed mesophase; and dyads bridged by the hexyloxy or ethanyloxy did not show liquid crystal properties in the heating or cooling circle. Electronic energy levels of triphenylene and perylene units of the dyads measured by cyclic voltammetry (CV) are almost the same as that of HAT6 and PMD6, respectively. In conclusion, these dyads have the potential application in the organic photovoltaic field.

Key words: discotic liquid crystal, triphenylene, perylene monoimide diester, dyad, photoinduced electron transfer

Cite this article

Kong Xiangfei, Liu Peng, Wang Guixia, Xia Liting, Dai Shengping, Su Jian, Liao Peihai, Liu Zheng, Mu Linping. Synthesis and Properties of Alkoxy-Bridged Triphenylene and Perylene Monoimide Diesters Dyads[J]. Chin. J. Org. Chem., 2016, 36(6): 1325-1334.

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烷氧基桥接的苯并菲和苝单亚胺二酯二元化合物的合成及性质研究

Synthesis and Properties of Alkoxy-Bridged Triphenylene and Perylene Monoimide Diesters Dyads

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