Synthesis and Photochromism of <i>2H</i> ‐Naphthopyrans With an Extended Conjugation Skeleton

Abstract Two series of new 2H‐naphthopyran derivatives with an extended conjugation skeleton—benzonaphthopyrans ( BNPs ) and naphthonaphthopyran ( NNPs )—have been designed and synthesized in this work. Their photochromic properties in organic solution and in poly(methyl methacrylate) (PMMA) have been investigated with special attention on the relationship between the extended conjugation skeleton and the photochromism. Compared to the simple benzopyran ( BP ) and the parent 2 H ‐naphthopyran (NP), both BNPs and NNPs exhibit much better photochromic properties, such as faster photo‐responsive and thermal fading rates, and excellent fatigue resistance, which indicates the extended conjugation skeleton can significantly improve the photochromic properties of 2 H ‐naphthopyran derivatives. This is a new strategy to develop photochromic 2 H ‐naphthopyrans with potential applications in fields such as ophthalmic lenses and photo‐information storage.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-05-28
DOI
https://doi.org/10.1002/ajoc.202500171
Primary Topic
Photochromic and Fluorescence Chemistry
Type
article
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article

Synthesis and Photochromism of 2H ‐Naphthopyrans With an Extended Conjugation Skeleton

Xi Tu, Haiying Xie, Jitian Rao, Jie Han et al.
Asian Journal of Organic Chemistry
Photochromic and Fluorescence Chemistry
article

Synthesis and Photochromism of 2H ‐Naphthopyrans With an Extended Conjugation Skeleton

Xi Tu, Haiying Xie, Jitian Rao, Jie Han, Ripei Shen
article en

Abstract

Abstract Two series of new 2H‐naphthopyran derivatives with an extended conjugation skeleton—benzonaphthopyrans ( BNPs ) and naphthonaphthopyran ( NNPs )—have been designed and synthesized in this work. Their photochromic properties in organic solution and in poly(methyl methacrylate) (PMMA) have been investigated with special attention on the relationship between the extended conjugation skeleton and the photochromism. Compared to the simple benzopyran ( BP ) and the parent 2 H ‐naphthopyran (NP), both BNPs and NNPs exhibit much better photochromic properties, such as faster photo‐responsive and thermal fading rates, and excellent fatigue resistance, which indicates the extended conjugation skeleton can significantly improve the photochromic properties of 2 H ‐naphthopyran derivatives. This is a new strategy to develop photochromic 2 H ‐naphthopyrans with potential applications in fields such as ophthalmic lenses and photo‐information storage.

Asian Journal of Organic ChemistryVol. 14(8)
Nankai University (CN), Zero to Three (US)
Openalex Percentile: Top 92%
Photochromic and Fluorescence Chemistry
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