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Anthraquinone‐Imide‐Based Dimers: Synthesis, Piezochromism, Liquid Crystalline and Near‐Infrared Electrochromic Properties
Author(s) -
Chen Fengkun,
Zhang Jie,
Wan Xinhua
Publication year - 2011
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201100065
Subject(s) - electrochromism , imide , anthraquinone , mesophase , cyclic voltammetry , chemistry , photochemistry , triphenylamine , materials science , polymer chemistry , organic chemistry , electrochemistry , electrode , phase (matter)
A series of anthraquinone‐imide‐based dimers, C5*‐AQI‐Si2, C5*‐AQI‐Si3, C5*‐AQI‐Si4, and C5*‐AQI‐Si8, have been prepared by the hydrosilylation of N ‐(hex‐5‐enyl)‐6‐(4′‐(( S )‐2‐methylbutoxy)phenyl)anthraquinone‐2,3‐dicarboxylic imide and hydride‐terminated siloxanes with different lengths. Their liquid crystalline behaviors, and piezochromic and near‐infrared electrochromic properties have been characterized by DSC, wide‐angle X‐ray diffraction, cyclic voltammetry, and UV–vis–NIR spectroscopy. Although anthraquinone imide is not liquid crystalline by itself, all the dimers formed a smectic A mesophase. Under moderate pressure, the color of the dimers changed from light yellow to deep red. Upon reduction to a radical anionic state, the dimers exhibited an intense NIR absorption at 844 nm. These anthraquinone‐imide‐based dimers are probably the first multifunctional molecules with combined liquid crystalline, mechanochromic, and NIR electrochromic properties.