Synthesis and Photochromic Properties of Diaryl [5]Helicene Derivatives

Synthesis and Photochromic Properties of Diaryl [5]Helicene Derivatives

Photoinduced tuning of aromaticity and correlative molecular properties has attracted enormous interest in recent years both for modulating photochromism properties and designing novel photochromic materials. Here, we report the synthesis and photochemical characterization of diaryl[5]helicene‐based...

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Published in:Chemistry : a European journal Vol. 29; no. 72; pp. e202302693 - n/a
Main Authors: Li, Ruiji, Fang, Qi, Chen, Minghui, Yamada, Mihoko, Tsuji, Yugo, Kugai, Yusuke, Li, Wei, Kawai, Tsuyoshi
Format: Journal Article
Language:English
Published: Germany Wiley Subscription Services, Inc 22-12-2023
Subjects:
Aromaticity
Bleaching
Chemistry
diarylethene
Ethene
Ethylene
Fluorescence
helicenes
Irradiation
Light irradiation
Molecular machines
Molecular properties
Phenanthrene
Photochemicals
Photochromism
Radiation
Switches
Synthesis
thermal cycloreversion reactions
helicenes
photochromism
thermal cycloreversion reactions
diarylethene
aromaticity
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Summary:Photoinduced tuning of aromaticity and correlative molecular properties has attracted enormous interest in recent years both for modulating photochromism properties and designing novel photochromic materials. Here, we report the synthesis and photochemical characterization of diaryl[5]helicene‐based diarylethene molecular switches. 3,4‐Bis(2,4‐dimethyl‐5‐phenylthiophen‐3‐yl)dibenzo[c,g]phenanthrene derivative 1 a showed no photochromic reaction, whereas 3,4‐bis(2‐methyl‐5‐phenylthiophen‐3‐yl)dibenzo[c,g]phenanthrene derivative 2 a and 3,4‐bis(5‐methyl‐2‐phenylthiazol‐4‐yl)dibenzo[c,g]phenanthrene derivative 3 a exhibited reversible photochromism in different aprotic solvents with specific light irradiation. Meanwhile, the diarylethene compounds 2 a and 3 a underwent turn‐off mode fluorescence photoswitching together with photoisomerization upon light irradiation. Remarkably, the photoinduced changes in the aromaticity of [5]helicene as a central ethene bridge along with the relative smaller activation energy and higher frequency factor facilitated the thermal bleaching rates of diarylethene switches 2 and 3 in solution. This research provides new insight for designing aromatic diarylethene photoswitches for reversible fluorescence switching, photoinduced changes in aromaticity and further fast thermal back reactions. Diaryl [5]helicene derivatives demonstrate well‐defined reversible photocyclization reactions with turn‐off mode fluorescent photoswitching behaviors upon photochromic reaction. The loss of aromaticity of the central benzene ring of [5]helicene along with the photocyclization reaction the thermal bleaching rate.
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302693