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Influence of silyloxy substitution on the photochromic properties of diarylbenzo- and naphthopyrans\(^{\S }\)

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Abstract

Diarylbenzopyrans and their annulated derivatives are a class of photochromic compounds, which have been extensively investigated for photochromism. In fact, some naphthopyrans are employed industrially in ophthalmic lens applications. Photoirradiation of 2,2-diphenylbenzopyran leads to the formation of colored o-quinonoid intermediates. The latter revert too rapidly to allow their observation only at low temperatures (173–263 K). Annulation and other strategies are exploited to observe the colored o-quinonoid intermediates that persist for a few minutes at room temperature. We have examined photochromism of a set of silyloxy-substituted 2,2-diphenylbenzo- and naphthopyrans to explore how the mesomeric effects transmitted by the strongly e-donating silyloxy group substituted in the ring and at phenyl groups manifest in the spectrokinetic properties of their photogenerated colored o-quinonoid intermediates. We show that silyloxy substitution in the benzopyran ring leads to remarkable stabilization of the colored intermediates to enable their persistence at 283 K for a few minutes. In contrast, similar substitution in the C2-phenyl rings destabilizes the colored intermediates.

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Acknowledgements

JNM is thankful to the Science and Engineering Research Board (SERB, Grant Number: SB/S2/JCB-52/2014), New Delhi, for financial support through the J. C. Bose fellowship. AM and VKM sincerely acknowledge the Council of Scientific and Industrial Research (CSIR), New Delhi for senior research fellowships. Mr. Debanjan Bhattacharjee is thanked for his contribution during the initial stages of the project.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology, Kanpur, Uttar Pradesh, 208 016, India

    Arindam Mukhopadhyay, Vijay Kumar Maka & Jarugu Narasimha Moorthy

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  1. Arindam Mukhopadhyay
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  2. Vijay Kumar Maka
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  3. Jarugu Narasimha Moorthy
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Correspondence to Jarugu Narasimha Moorthy.

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\(^{\S }\)In honor of Prof. M. V. George on the occasion of his 90\(^\mathrm{th}\) Birthday.

Special Issue on Photochemistry, Photophysics and Photobiology

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Mukhopadhyay, A., Maka, V.K. & Moorthy, J.N. Influence of silyloxy substitution on the photochromic properties of diarylbenzo- and naphthopyrans\(^{\S }\). J Chem Sci 130, 140 (2018). https://doi.org/10.1007/s12039-018-1542-0

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  • DOI: https://doi.org/10.1007/s12039-018-1542-0

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