Heterocyclic quinol-type fluorophores. Synthesis of novel imidazoanthraquinol derivatives and their photophysical properties in benzene and in the crystalline state
Heterocyclic quinol-type fluorophores. Synthesis of novel imidazoanthraquinol derivatives and their photophysical properties in benzene and in the crystalline state
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DOI：
10.1039/b410311d
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发表时间：
2005-02
影响因子：
3.3
通讯作者：
Y. Ooyama;T. Nakamura;Katsuhira Yoshida
中科院分区：
文献类型：
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作者：
Y. Ooyama;T. Nakamura;Katsuhira Yoshida
已经开发出一对新型咪唑蒽醌荧光团 2 和 3，其咪唑环可能具有两种互变异构形式（A 和 B）。为了控制互变异构形式以提高荧光性能，进一步合成了N-丁基咪唑衍生物6和7。苯中对羟基苯酚的荧光强度顺序为 3 ≪ 6 < 7 < 2，这与结晶状态下的 3 ≪ 2 ≪ 6 < 7 有很大不同。为了研究咪唑环的 N-烷基化对溶液中和结晶状态下对苯二酚荧光团光物理性质的影响，我们进行了半经验分子轨道计算（AM1 和 INDO/S）和 X 射线晶体学分析。根据计算结果和X射线晶体结构，讨论了N-烷基化对羟基喹啉荧光团化学结构及其固态光物理性质的影响。
An isomeric pair of novel imidazoanthraquinol fluorophores 2 and 3 exhibiting two tautomeric forms (A and B) that are possible for the imidazole ring have been developed. In order to control the tautomeric form to improve the fluorescence properties, the N-butylated imidazole derivatives 6 and 7 have further been synthesized. The fluorescence intensity of the quinols was in the order 3 ≪ 6 < 7 < 2 in benzene, which is quite different from the order 3 ≪ 2 ≪ 6 < 7 in the crystalline state. To investigate the effect of N-alkylation of imidazole ring on the photophysical properties of the quinol fluorophores in solution and in the crystalline state, we have performed semi-empirical molecular orbital calculations (AM1 and INDO/S) and X-ray crystallographic analysis. On the basis of the results of calculations and the X-ray crystal structures, the N-alkylation effects on the chemical structure of the quinol fluorophores and on their solid-state photophysical properties are discussed.