Diarylethene compounds are functional molecules possessing excellent photochromic properties, exhibiting reversible isomerization between open- and closed-ring forms upon light irradiation. Their most prominent feature, compared to other photoresponsive molecules like azobenzene, is their exceptionally high thermal stability in both states, alongside robust fatigue resistance capable of withstanding repeated isomerization cycles.^1,2)

In particular, "fluorine-containing diarylethenes," which incorporate a fluorine-substituted structure such as a perfluorocyclopentene ring at the bridging site, exhibit a highly stabilized energy state in the closed-ring form due to the strong electron-withdrawing nature of fluorine.

In the fields of drug discovery and life sciences, these compounds are utilized as building blocks for controlling the functions of new modalities like peptides, as well as "inhibitors with photo-switching functions" that enable the temporal and spatial manipulation of binding affinity with target proteins.^3,4)

Furthermore, in electronic materials and material science, leveraging their overwhelming stability, they find applications as ultra-high-density, next-generation optical memories capable of long-term data retention, and as molecular-level switching elements for electrical conductivity and fluorescence properties.^1,2)

We offer a lineup of diarylethene compounds with functional groups including chloro, carboxy, and formyl groups.

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Products

P3391

3,3'-(Perfluorocyclopent-1-ene-1,2-diyl)bis(5-chloro-2-methylthiophene)

B7084

1,2-Bis(5-chloro-2-methylthiophen-3-yl)cyclopent-1-ene

C4222

4,4'-(Cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2-carboxylic Acid)

C4285

4,4'-(Cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2-carbaldehyde)

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References

1. 1) Diarylethenes for Memories and Switches
   • M. Irie, Chem. Rev. 2000, 100, 5, 1685.
2. 2) Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators
   • M. Irie, T. Fukaminato, K. Matsuda, S. Kobatake, Chem. Rev. 2014, 114, 12174.
3. 3) Photopharmacology: Beyond Proof of Principle
   • W. A. Velema, W. Szymanski, B. L. Feringa, J. Am. Chem. Soc. 2014, 136, 6, 2178.
4. 4) Structure–Activity Relationships of Photoswitchable Diarylethene-Based β-Hairpin Peptides as Membranolytic Antimicrobial and Anticancer Agents
   • O. Babii, S. Afonin, A. Yu. Ishchenko, T. Schober, A. O. Negelia, G. M. Tolstanova, L. V. Garmanchuk, L. I. Ostapchenko, I. V. Komarov, A.S. Ulrich, J. Med. Chem. 2018, 61, 10793.

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cis-1,2-Dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene

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2,3-Bis(2,4,5-trimethyl-3-thienyl)maleic Anhydride

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4,4'-(Cyclopent-1-ene-1,2-diyl)bis(5-methylthiophene-2-carboxylic Acid)

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3,3'-(Perfluorocyclopent-1-ene-1,2-diyl)bis(5-chloro-2-methylthiophene)

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1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-1-cyclopentene

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1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene (purified by sublimation)

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Related Product Category Page

• Photochromic Dyes

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