Piezochromic luminescence of amide and ester derivatives of tetraphenylpyrene-role of amide hydrogen bonds in sensitive piezochromic response
Piezochromic luminescence of amide and ester derivatives of tetraphenylpyrene-role of amide hydrogen bonds in sensitive piezochromic response
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DOI：
10.1039/c0jm03950k
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发表时间：
2011-01-01
影响因子：
--
通讯作者：
Araki, Koji
中科院分区：
文献类型：
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作者：
Sase, Mitsutaka;Yamaguchi, Shingo;Araki, Koji
合成了一系列1，3，6，8-四苯基芘（TPPy）的酰胺和酯类衍生物，研究了它们的固态发光、分子堆积和压致变色响应，以改进和完善基于多氢键和盘状芳香核的紧密堆积作为控制分子堆积的竞争因素的压致变色发光材料的设计理念。具有己基侧链的TPPy的酰胺衍生物（1b）在相对低的施加压力下显示出灵敏的发光响应，这归因于氢键导向的H型柱状堆积。较高的压力的应用引起相当大的破坏的氢键导向的结构，导致紧密堆积的状态是压倒一切的因素，指导分子组装，并表现出类似的压致变色反应的酯衍生物。在此基础上，详细讨论了酰胺氢键和侧链的作用。
A series of amide and ester derivatives of 1,3,6,8-tetraphenylpyrene (TPPy) were prepared, and their solid-state luminescence, molecular packing, and piezochromic responses were studied in order to improve and refine the design concept of piezochromic luminescent materials based on the use of multiple hydrogen bonds and close packing of disk-shaped aromatic cores as competing factors in the control of molecular packing. The amide derivative of TPPy having hexyl side chains (1b) showed a sensitive luminescence response at a relatively low applied pressure, which was ascribed to the hydrogen bond-directed H-type columnar packing. Application of higher pressure induced considerable destruction of the hydrogen bond-directed structure, leading to the state where close packing was the overriding factor directing the molecular assembly and showed similar piezochromic response to that of the ester derivative. Based on the results, the role of the amide hydrogen bonds and the side chains was discussed in detail.