Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1444-1449.DOI: 10.6023/cjoc201901003 Previous Articles     Next Articles

Articles

6-甲氧基喹唑啉酮-吡啶二氟硼染料的合成及发光性能研究

周佳a, 刘璐a, 钟成b, 傅杨a, 宋智彬a, 彭以元a   

  1. a 江西师范大学化学化工学院 功能有机小分子教育部重点实验室 南昌 330022;
    b 武汉大学化学与分子科学学院 武汉 430072
  • 收稿日期:2019-01-03 修回日期:2019-02-03 出版日期:2019-05-25 发布日期:2019-02-22
  • 通讯作者: 宋智彬 E-mail:zbsong@jxnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21606116,51873160)、江西省自然科学基金(No.20161BAB213070)和江西省教育厅科技(No.GJJ170176)资助项目.

Synthesis and Luminescent Properties of 6-Methoxy-quinazolinone-pyridine Difluoroboron Dyes

Zhou Jiaa, Liu Lua, Zhong Chengb, Fu Yanga, Song Zhibina, Peng Yiyuana   

  1. a Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022;
    b College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
  • Received:2019-01-03 Revised:2019-02-03 Online:2019-05-25 Published:2019-02-22
  • Contact: 10.6023/cjoc201901003 E-mail:zbsong@jxnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21606116, 51873160), the Natural Science Foundations of Jiangxi Province (No. 20161BAB213070) and the Department of Education of Jiangxi Province (No. GJJ170176).

6-Methoxyquinazolinone-pyridine difluoroboron dyes (BODIQPys) have been synthesized in two simple steps with 2-amino-5-methoxybenzamide and 2-methylpyridines as starting materials. These quinazolinone-based difluoroboron (BF2) complexes exhibited highly efficient green luminescence and remarkable fluorescence in the solid-state with very large Stokes shift (Δλ up to 220 nm in MeCN). The introduction of methoxy group at 6-position of BODIQPy caused the red-shifted emission by the enhancement of charge transfer property. The introduction of halogen atom at pyridine moiety of BODIQPy can tune the LUMO levels in regularity while their HOMO levels remain intact.

Key words: quinazolinone, difluoroboron complexes, fluorescent dyes, solid state luminescence