Methylated Unsymmetric BODIPY Compounds: Synthesis, High Fluorescence Quantum Yield and Long Fluorescence Time

  • Xian-Fu ZhangEmail author
  • George Q. Zhang
  • Jiale Zhu


We show that unsymmetric BODIPY compounds with one, two, and three methyl groups can be synthesized easily and efficiently by the unsymmetric reaction method. Their steady state and time-resolved fluorescence properties are examined in solvents of different polarity. These compounds show high fluorescence quantum yields (0.87 to 1.0), long fluorescence lifetimes (5.89 to 7.40 ns), and small Stokes shift (199 to 443 cm−1). The methyl substitution exhibits influence on the UV-Vis absorption and fluorescence properties, such as the blue shift in emission and absorption spectra. It is the number rather than the position of methyls that play major roles. Except for 3 M-BDP, the increase in the number of methyls on BODIPY core leads to the increase in both fluorescence quantum yield and radiative rate constant, but causes the decrease in fluorescence lifetime. H-bonding solvents increase both the fluorescence lifetime and quantum yields. The methylated BODIPYs show the ability to generate singlet oxygen (1Δg) which is evidenced by near-IR luminescence and DPBF chemical trapping techniques. The formation quantum yield of singlet oxygen (1Δg) for the compounds is up to 0.15 ± 0.05.


Unsymmetric BODIPY Fluorescence Synthesis Absorption Methyl substitution 



We thank the financial support from Hebei Provincial Hundred Talents Plan (Contract E2013100005), Hebei Provincial Natural Science Foundation (Contract B2014407080).

Supplementary material

10895_2019_2349_MOESM1_ESM.doc (684 kb)
ESM 1 (DOC 683 kb)


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Institute of Applied PhotochemistryHebei Normal University of Science and TechnologyQinhuangdaoChina
  2. 2.MPC TechnologiesHamiltonCanada
  3. 3.Department of Electrical & Computer EngineeringMcMaster UniversityHamiltonCanada

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