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Synthesis and photochromic properties of new naphthopyrans

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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).

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Authors and Affiliations

  1. Ying-Zhong Shen, Applied Chemistry Department, College of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, 29 Yudao St., Nanjing, 210016, P. R. China

    Qian Zhao, Yanhua Yang, Yingxiang Duan & YingZhong Shen

  2. Jiangsu MO Opto-Electronic Material Co. Ltd., 1 Qinglongshan Branch Road, Zhenjiang New District, Zhenjiang, 212132, P. R. China

    Xian Tao

Authors
  1. Qian Zhao
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  3. Yingxiang Duan
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Correspondence to YingZhong Shen.

Additional information

Supplementary information file containing IR, 1H and 13C NMR spectral data of all synthesized compounds, synthetic procedure of compound NOP1, and optical density change curves of compounds NOP1–3 in CH2Cl2 and PMMA is available on the journal website at http:// link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(9), 840–847

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Zhao, Q., Yang, Y., Duan, Y. et al. Synthesis and photochromic properties of new naphthopyrans. Chem Heterocycl Comp 54, 840–847 (2018). https://doi.org/10.1007/s10593-018-2366-z

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  • DOI: https://doi.org/10.1007/s10593-018-2366-z

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