Crystal Growth and Characterization of Fluorinated Perylene Diimides

doi:10.1007/s40242-013-3294-1

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (1): 63-67.doi: 10.1007/s40242-013-3294-1

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Crystal Growth and Characterization of Fluorinated Perylene Diimides

HUANG Jiachi, LI Hanying, MO Xiong, SHI Minmin, WANG Mang, CHEN Hongzheng

State Key Laboratory of Silicon Materials, Key Laboratory of Macromolecular Synthesis and Functionalization, Ministry of Education, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, P. R. China

Received:2013-07-12 Revised:2013-08-08 Online:2014-02-01 Published:2013-09-02
Contact: LI Hanying,E-mail:hanying_li@zju.edu.cn; CHEN Hongzheng,E-mail:hzchen@zju.edu.cn E-mail:hanying_li@zju.edu.cn; hzchen@zju.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.51222302, 50990063, 91233114), the Natural Science Foundation of Zhejiang Province, China(No.LZ13E030002) and the Fundamental Research Funds for the Central Universities of China(No.2012QNA4025).

Abstract

Abstract:

One-dimensional crystals of fluorinated perylene diimides were achieved by the self-assembly of them via solvent-nonsolvent exchanging. The π-conjugated fluorinated perylene diimides were assembled into highly-ordered nanostructures of well-defined morphologies in organic solvents due to the π-π interaction between the aromatic cores. It was found that with more introduced F atoms, perylene diimides showed remarkably improved solubility and thus were much easier to grow into crystals, due to the increased polarity induced by the strong electron-withdrawing F group. More importantly, single crystal of N,N'-diperfluorophenyl-3,4,9,10-perylenetetracarboxylic diimide(DPFPP) was obtained, and the unit cell-dimensions of triclinic structure were determined by the selected area electron diffraction(SAED) patterns to be a=0.712 nm, b=1.072 nm, c=2.914 nm, α=97.0°, β=89.6°, γ=93.4°. Owing to most of the longest c-axis orienting nearly vertically to the long axis of the needle crystal, the molecular planes are expected to be vertical to the needle axis.

Key words: Perylene diimide, Fluorination, Crystal growth

HUANG Jiachi, LI Hanying, MO Xiong, SHI Minmin, WANG Mang, CHEN Hongzheng. Crystal Growth and Characterization of Fluorinated Perylene Diimides[J]. Chemical Research in Chinese Universities, 2014, 30(1): 63-67.

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Crystal Growth and Characterization of Fluorinated Perylene Diimides

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