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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 9, pp 840–847 | Cite as

Synthesis and photochromic properties of new naphthopyrans

  • Qian Zhao
  • Yanhua Yang
  • Yingxiang Duan
  • Xian Tao
  • YingZhong Shen
Article
  • 31 Downloads

Two novel isomeric naphthopyrans substituted with phenyl (13-butyl-6,7-dimethoxy-3,3-bis(6-methoxybiphenyl-3-yl)-3,13-dihydrobenzo[h]indeno[2,1-f]chromen-13-ol) and 4-(naphthalen-1-yl)phenyl (13-butyl-6,7-dimethoxy-3,3-bis[6-methoxy-4'-(naphthalenyl)-biphenyl-3-yl]-3,13-dihydrobenzo[h]indeno[2,1-f]chromen-13-ol) moieties were synthesized. Their photochromism, electrochemical and fluorescent properties were investigated. They displayed faster color fading rate and larger fluorescence quantum yield than 13-butyl-6,7-dimethoxy-3,3-bis(4-methoxyphenyl)-3,13-dihydrobenzo[h]indeno[2,1-f]chromen-13-ol. Moreover, they showed excellent photochromic and fluorescent properties both in solution and in polymethylmethacrylate film. In addition, cyclic voltammetry tests showed that the aromatic substituents had a significant effect on the electrochemical behavior of the naphthopyran derivatives.

Keywords

naphthopyran electrochemistry fluorescence photochromism wavelength 

Notes

The authors are grateful to the financial support from industry (1006-KFA17783). A project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Supplementary material

10593_2018_2366_MOESM1_ESM.pdf (2.7 mb)
ESM 1 (PDF 2798 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Qian Zhao
    • 1
  • Yanhua Yang
    • 1
  • Yingxiang Duan
    • 1
  • Xian Tao
    • 2
  • YingZhong Shen
    • 1
  1. 1.Ying-Zhong Shen, Applied Chemistry Department, College of Material Science and TechnologyNanjing University of Aeronautics and AstronauticsNanjingP. R. China
  2. 2.Jiangsu MO Opto-Electronic Material Co. Ltd.ZhenjiangP. R. China

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