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基于线性聚醚的1-和2-蒽芳香族羧酰胺作为化学传感器时取代位置对扭曲分子内电荷转移的影响

Substituted position effect on twisted intramolecular charge transfer of 1- and 2-anthracene aromatic carboxamides as chemosensors based on linear polyether.

作者信息

Kim Jeongsik, Morozumi Tatsuya, Hiraga Hisafumi, Nakamura Hiroshi

机构信息

Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.

出版信息

Anal Sci. 2009 Nov;25(11):1319-25. doi: 10.2116/analsci.25.1319.

DOI:10.2116/analsci.25.1319
PMID:19907089
Abstract

Bi-chromophoric compounds linked to linear polyether N,N'-[oxybis(3-oxapentamethyleneoxy-2-phenyl)]-bis(1-anthracenecarboxamide) (1(4)) and its analogues (1(5), 2(4) and 2(5)) were synthesized. Their photochemical properties and complexation actions were investigated in acetonitrile. These fluoroionophores have shown weak emissions in the absence of guest ions, resulting in a twisted intramolecular charge transfer (TICT) quenching process (off state) of an anthracene aromatic amide moiety. After the formation of a complex with alkaline earth metal ions, a large enhancement of fluorescent intensities was obtained (on state). The efficiencies of controlling an off-on fluorescent signal using 1(4) and its analogues (1(5), 2(4) and 2(5)) were larger than that of the 9-positioned analogue. These results suggested that the TICT relaxation process was effectively able to control using 1(4) and its analogues (1(5), 2(4) and 2(5)) by complex formations.

摘要

合成了与线性聚醚N,N'-[氧双(3-氧杂戊亚甲基氧基-2-苯基)]-双(1-蒽甲酰胺)(1(4))及其类似物(1(5)、2(4)和2(5))相连的双发色团化合物。在乙腈中研究了它们的光化学性质和络合作用。这些氟离子载体在没有客体离子的情况下表现出微弱的发射,导致蒽芳香酰胺部分发生扭曲的分子内电荷转移(TICT)猝灭过程(关闭状态)。与碱土金属离子形成络合物后,荧光强度大幅增强(开启状态)。使用1(4)及其类似物(1(5)、2(4)和2(5))控制荧光信号开关的效率高于9位类似物。这些结果表明,通过络合物的形成,利用1(4)及其类似物(1(5)、2(4)和2(5))能够有效地控制TICT弛豫过程。

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