Mechano‐ and Photoresponsive Behavior of a Bis(cyanostyryl)benzene Fluorophore

The mechanoresponsive behavior and photochemical response of a new bis(cyanostyryl)benzene fluorophore (CSB‐5) were investigated. Green fluorescence with λem,max of 507 nm was found for CSB‐5 in chloroform solution, mirroring the behavior of a previously reported similar dye (CSB‐6). Alternatively,...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-04, Vol.25 (24), p.6162-6169
Main Authors: Kaneko, Ryohei, Sagara, Yoshimitsu, Katao, Shouhei, Tamaoki, Nobuyuki, Weder, Christoph, Nakano, Hideyuki
Format: Article
Language:English
Subjects:
Benzene
bis(cyanostyryl)benzene analogue
Chemistry
Chloroform
Color
Crystal structure
Crystallinity
Emission
emission color change
Excimers
Fluorescence
Glass substrates
Hydrocarbons
Mechanoluminescence
morphology
Photochemical reactions
Photochemicals
photochemistry
Powder
Ultraviolet radiation
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Summary:The mechanoresponsive behavior and photochemical response of a new bis(cyanostyryl)benzene fluorophore (CSB‐5) were investigated. Green fluorescence with λem,max of 507 nm was found for CSB‐5 in chloroform solution, mirroring the behavior of a previously reported similar dye (CSB‐6). Alternatively, crystalline samples of CSB‐5 exhibited orange fluorescence with λem,max of 620 nm, attributable to excimer emission. Although the emission color change was not clearly noticeable by naked eye, CSB‐5 exhibited mechanochromic luminescence, due to transformation into the amorphous state upon grinding the crystalline powder. Interestingly, rubbed films of CSB‐5 prepared on glass substrates exhibited a pronounced emission color change from orange to green when exposed to UV light. This response is the result of a photochemical reaction that occurs in the amorphous state and which causes a decrease of the excimer emission sites so that the emission color changes from excimer to monomer. The crystalline material did not display such a photoinduced emission color change and the difference in photochemical reactivity between crystalline and amorphous states was exploited to pattern the emission color of rubbed films. Emission patterning: Rubbed films of a new bis(cyanostyryl)benzene derivative (CSB‐5) exhibit a pronounced photoinduced emission color change. This effect is the result of photochemical reactions that only take place in the amorphous state, which can be mechanically accessed.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201900120