Synthesis, crystal structure and optoelectronic properties of a new unsymmetrical photochromic diarylethene.
A new unsymmetrical photochromic diarylethene, 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-methyl-5-(3-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene (1a), was synthesized and its structure was determined by single-crystal X-ray diffraction analysis. Its optical and electrochemical properties, including photochromic reactivity both in solution and in the solid state (PMMA film and the single-crystalline phase), fluorescence and electrochemical properties were investigated in detail. The compound showed excellent photochromism even in the single-crystalline phase by photo-irradiation. In acetonitrile, the open-ring isomer of diarylethene 1 exhibited relatively strong fluorescence at 470 nm when excited at 300 nm, and its emission intensity decreased along with the photochromism upon irradiation with 313 nm light. Its closed-ring isomer showed almost no fluorescence. The electrochemical properties of diarylethene were investigated by performing cyclic voltammetry experiment and its HOMO and LUMO energy level were calculated.
Yang
Tianshe
T
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, PR China.
Pu
Shouzhi
S
Fan
Congbin
C
Liu
Gang
G
D018360:Crystallography, X-Ray; D004563:Electrochemistry; D004583:Electrons; D005030:Ethylenes / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013053:Spectrophotometry; D013237:Stereoisomerism
D005030:Ethylenes; C036216:ethylene