A New Series of C-6 Unsubstituted Tetrahydropyrimidines: Convenient One-Pot Chemoselective Synthesis, Aggregation-Induced and Size-Independent Emission Characteristics

被引：55
|
作者：
Zhu, Qiuhua [1 ]
Huang, Lan [1 ]
Chen, Zhipeng [1 ]
Zheng, Sichao [1 ]
Lv, Longyun [1 ]
Zhu, Zhibo [1 ]
Cao, Derong [2 ]
Jiang, Huanfeng [2 ]
Liu, Shuwen [1 ]
机构：
[1] So Med Univ, Sch Pharmaceut Sci, Guangzhou 510515, Guangdong, Peoples R China
[2] S China Univ Technol, Sch Chem & Chem Engn, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 04期
关键词：
aggregation-induced emission; multicomponent reactions; nitrogen heterocycles; size-independent emission; tetrahydropyrimidine; PART; 2; MULTICOMPONENT; ELECTROLUMINESCENCE; FLUORESCENCE; EMITTERS; ANALOGS; STATES;
D O I：
10.1002/chem.201203012
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new series of C-6 unsubstituted tetrahydropyrimidines 6 have been directly synthesized via a convenient urea-catalyzed chemoselective five-component reaction (5CR) under mild conditions. Compounds 6 show typical aggregation-induced emission enhancement (AIEE) characteristics because they are practically no emissive in solution but emit blue or green fluorescence in aggregates with fluorescence yield up to 93?%. One of the 5CR products, 6?aa, exhibits blue- and green-fluorescence aggregates (bf- and gf-aggregates). The bf- and gf-aggregates are prepared under different conditions and proved to result from different J-aggregations by single-crystal X-ray analysis. In addition, the bf- and gf-aggregates of 6?aa show unusual size-independent emission (SIE) characteristics because their maximum emission wavelengths in different sizes (suspension particles, film, powder and crystals) are the same, 434 and 484 nm, respectively. Based on the obtained experimental results, the 5CR mechanism, the origins of AIEE and SIE characteristics are discussed.
引用
收藏
页码：1268 / 1280
页数：13
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