Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene

Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX010, which shows switchable near-IR and blue fluorescence responses. Detai...

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Published inJournal of the American Chemical Society Vol. 137; no. 20; pp. 6436 - 6439
Main Authors Tanioka, Masaru, Kamino, Shinichiro, Muranaka, Atsuya, Ooyama, Yousuke, Ota, Hiromi, Shirasaki, Yoshinao, Horigome, Jun, Ueda, Masashi, Uchiyama, Masanobu, Sawada, Daisuke, Enomoto, Shuichi
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 27.05.2015
Subjects
Fluoresceins - chemistry
Fluorescence
Infrared Rays
Molecular Structure
Xanthenes - chemistry
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Summary:Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX010, which shows switchable near-IR and blue fluorescence responses. Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion between the two molecular packing arrangements in response to mechanical grinding and solvent vapor-fuming.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b00877