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Synthesis, Luminescent Properties of aza-Boron-Diquinomethene Difluoride Complexes and Their Application for Fluorescent Security Inks

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Abstract

Two aza-boron-diquinomethene (aza-BODIQU) complexes bearing phenyl and carbazyl substituents were synthesized and characterized. Their photophysical properties were investigated systematically via spectroscopic and theoretical methods. Both complexes exhibit strong 1π-π* transition absorptions (λ abs = 400–540 nm) and intense fluorescent emissions (λ em = 440–600 nm, Φ PL  = 0.93 and 0.78) in CH2Cl2 solution and in solid state at room temperature. Compared to the complex with phenyl groups, the complex bearing carbazyl groups shows significant bathochromic shift in both absorption and emission. This could be attributed to the larger π-electron conjugation of the carbazole unit and intramolecular charge transfer feature from carbazole to aza-BODIQU component. In addition, the complexes exhibit intense photoluminescence and good stability on antacid, anti-alkali and stability in printing ink samples, which makes them potential dopants for the application of fluorescent security inks.

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Acknowledgments

The authors greatly acknowledge the financial support by Natural Science Foundation of the Jiangsu Higher Education Institutions of China (13KJB150018), Natural Science Foundation of Jiangsu Province (BK20130926, BK20150123), National Natural Science Foundations of China (2012, 21203094; 2013, 21373112) and Scientific Research Starting Foundation for Returned Overseas Chinese Scholars, Ministry of Education, China. The authors also thank Dr. Yuan Guolin in Ink technology Research Institute for the security inks measurements.

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Authors and Affiliations

  1. Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, 210009, China

    Long Gu, Rui Liu, Qiang Wang, Guangliang Song, Xiaolin Zhu & Hongjun Zhu

  2. Jiangsu Vocational College of Information Technology, Wuxi, 214153, China

    Hong Shi

  3. Shanghai Institute of Technical Physics, Chinese Academy of Sciences, Shanghai, 200083, China

    Shidong Yuan

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  1. Long Gu
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  2. Rui Liu
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  3. Hong Shi
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Correspondence to Rui Liu or Hongjun Zhu.

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Gu, L., Liu, R., Shi, H. et al. Synthesis, Luminescent Properties of aza-Boron-Diquinomethene Difluoride Complexes and Their Application for Fluorescent Security Inks. J Fluoresc 26, 407–412 (2016). https://doi.org/10.1007/s10895-015-1727-6

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  • DOI: https://doi.org/10.1007/s10895-015-1727-6

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