Near-Infrared Electrochromic and Chiroptical Switching Materials: Design, Synthesis, and Characterization of Chiral Organogels Containing Stacked Naphthalene Diimide Chromophores
Near-Infrared Electrochromic and Chiroptical Switching Materials: Design, Synthesis, and Characterization of Chiral Organogels Containing Stacked Naphthalene Diimide Chromophores
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近红外电致变色和手性光学开关材料：含有堆叠萘二酰亚胺发色团的手性有机凝胶的设计、合成和表征
DOI：
10.1021/cm8014644
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发表时间：
2008-09
影响因子：
8.6
通讯作者：
Wan, Xinhua
中科院分区：
文献类型：
--
作者：
Wang, Zhi Yuan;Zheng, Jia;Qiao, Wenqiang;Gao, Jian Ping;Wan, Xinhua
利用低分子量凝胶作为手性支架，电致变色发色团作为刺激响应触发器，在可见和近红外光谱区域实现了手性开关材料，并由于手性凝胶中发色团的电子状态变化而工作。N,N ' -双（4-苯基-2,3,4,6-四- o -乙酰基-β-d-葡萄糖吡喃苷）-1,4,5,8-萘四羧基二酸酐与含糖胺亚酰化合成的N，N ' -二（4-苯基-2,3,4,6-四- o -乙酰基-β-d-葡萄糖吡喃苷）-1,4,5,8-萘四羧基二酰亚胺在室温下可形成稳定的手性凝胶。在可见和近红外光谱区，氧化还原活性凝胶在萘二亚胺的三种氧化还原态（中性、阴离子、阴离子）之间表现出可逆的、剧烈的圆二色性变化。手性凝胶中堆叠的萘二亚胺发色团在1310 ~ 1550 nm处被还原为自由基阴离子态时，产生了较大的圆二色性。
Chiroptical switching materials in the visible and near-infrared spectral regions have been realized using a low molecular weight gel as a chiral scaffold and electrochromic chromophores as a stimulus-responsive trigger and operate as a result of the change in the electronic states of the chromophores within the chiral gel. N,N′-Bis(4-phenyl-2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside)-1,4,5,8-naphthalenetetracarboxylic diimide, synthesized by imidization of 1,4,5,8-naphthalenetetracarboxylic dianhydride with a sugar-bearing amine, can form stable chiral gels at room temperature. The redox-active gels exhibited reversible and drastic changes in circular dichroism in the visible and near-infrared spectral region between the three redox states (neutral, radical anion, dianion) of the naphthalene diimide chromophore. A large circular dichroism at 1310−1550 nm was induced when the stacked naphthalene diimide chromophores in the chiral gels were reduced to the radical anion state.