化学学报 ›› 2008, Vol. 66 ›› Issue (9): 1134-1138. 上一篇    

研究简报

含磷酰杂菲苯甲酸对苯二酯的聚集诱导发光增强性能及其在检测过渡金属离子中的应用

钱立军1,2,佟斌1,支俊格3,杨帆1,申进波1,石建兵1,董宇平*,1   

  1. (1北京理工大学材料科学与工程学院 北京 100081)
    (2 北京工商大学材料科学与工程系 北京 100037)
    (3北京理工大学理学院 北京 100081)
  • 投稿日期:2007-11-10 修回日期:2007-12-12 发布日期:2008-05-14
  • 通讯作者: 董宇平

Aggregation-Induced Emission Enhancement of Phosphaphenanthrene-Containing p-Phenylene Dibenzoate and Its Application to Detecting Transition Metal Ions

QIAN Li-Jun12 TONG Bin1 ZHI Jun-Ge3 YANG Fan1 SHEN Jin-Bo1 SHI Jian-Bing1 DONG Yu-Ping*1   

  1. (1 College of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081)
    (2 Department of Materials Science and Engineering, Beijing Technology and Business University, Beijing 100037)
    (3 College of Science, Beijing Institute of Technology, Beijing 100081)
  • Received:2007-11-10 Revised:2007-12-12 Published:2008-05-14
  • Contact: DONG Yu-Ping

有机化合物因成膜以后荧光淬灭而使其应用受到很大限制, 所以研究、开发能在聚集状态下呈现优异发光性能的新材料就尤为重要. 由于分子间π-π和极性共同相互作用, 使得磷酰杂菲环的转动受到限制, 从而使苯甲酸-2-[6-氧化-6-氢-二苯基(c,e)<1,2>氧杂磷酰基]-1,4-二羟基苯二酯(OP)在达到一定规整聚集程度时, 荧光强度成倍增加, 具有了聚集诱导发光增强(AIEE)性质. 实验结果表明: 浓度低于1×10-6 mol•L-1 的OP会失去AIEE性质; 浓度为1×10-4 mol•L-1的Hg2+, Fe2+和 Fe3+会分别淬灭浓度为1×10-5 mol•L-1 OP荧光强度的26%, 34%, 74%, 而Pb2+, Zn2+, Cd2+, Co2+, Mn2+, Cu2+, Ni2+, Ag等离子的淬灭效率却很低, 这一性质表明该化合物可以用作过渡金属离子的特异性检测材料.

关键词: 磷酰杂菲, 聚集诱导发光增强, 分子内转动受限, 金属离子传感器

Fluorescence of the organic light-emitting compounds is often quenched when the luminophors are fabricated into solid thin films, which has greatly limited their scope of practical applications. So, it is important to design and synthesize the novel organic luminophors with excellent light emission property in the solid state. When 6-oxa-5-oxo-5-[2,5-di(benzoyloxyphenyl)]-5-phosphaphenanthrene (OP) aggregates to a certain degree, the fluorescence strength of OP increases proportionably, which shows obvious aggregation-induced emission enhancement (AIEE) property because the aggregation state of OP restricts rotation of the phosphaphenanthrene groups based on π-π stacking and polarity interaction between the molecules. The experimental result indicates that the concentration of OP influences AIEE property. If OP concentration was lower than 1×10-6 mol•L-1, AIEE property disappeared. Hg2+, Fe2+ and Fe3+ ions (1×10-4 mol• L-1) can efficiently quench the emission intensity of OP (2×10-5 mol•L-1) during the aggregation state formation, with the quenching efficiency to OP fluorescence being 26%, 34%, 74%, respectively and higher than those by Pb2+, Zn2+, Cd2+, Co2+, Mn2+, Cu2+, Ni2+ and Ag ions. This novel phenomenon may enable the molecule to find applications to discriminating chemosensors to detect the transition metal ions.

Key words: phosphaphenanthrene, aggregation-induced emission enhancement, restriction of intramolecular rotation, sensor to metal ion