Phthalimide Compounds Containing a Trifluoromethylphenyl Group and Electron-Donating Aryl Groups: Color-Tuning and Enhancement of Triboluminescence

Trifluoromethylphenyl-substituted phthalimide derivatives favorably form triboluminescence (TL) active noncentrosymmetric crystals. Oligothienyl-, oligophenyl-, and naphthyl-substituted phthalimide derivatives were successfully developed as a series of metal free TL compounds. X-ray crystal structur...

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Published inJournal of organic chemistry Vol. 81; no. 2; pp. 433 - 441
Main Authors Nishida, Jun-ichi, Ohura, Hokuto, Kita, Yasuyuki, Hasegawa, Hiroyuki, Kawase, Takeshi, Takada, Noriyuki, Sato, Hiroyasu, Sei, Yoshihisa, Yamashita, Yoshiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.01.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FLUORESCENCE
LUMINESCENCE
SPECTROSCOPY
COMPLEXES
LIGHT
INTENSITY
CRYSTAL-STRUCTURES
EMISSION
SHOCK-WAVE
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Summary:Trifluoromethylphenyl-substituted phthalimide derivatives favorably form triboluminescence (TL) active noncentrosymmetric crystals. Oligothienyl-, oligophenyl-, and naphthyl-substituted phthalimide derivatives were successfully developed as a series of metal free TL compounds. X-ray crystal structure analyses of bithienyl and naphthyl derivatives revealed noncentrosymmetric layer structures in the same direction. Introduction of suitable electron rich π-units such as thienyl groups enhances their photoluminescence and TL characteristics, and the colors can be also controlled in the visible region. A rigid naphthyl-substituted imide derivative exhibits extremely high TL performance.
Bibliography:KAKEN
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02191