Nav: Home

Direct synthesis of azulene continues to reveal alluring properties

February 06, 2020

Azulene is a pretty neat substance. As the name suggests, it displays a peculiar blue color. First synthesized in the 1930s, azulene has been used in medicine for its bioactive properties. Now azulene derivatives are being studied for use in organic electronics such as n-type semiconductors, solar cells and non-linear optics. This is made possible by the functionalization of the azulene ring. Odd-positions of the ring had been researched extensively for their high reactivity, though it was hard to select their functionality due to their electronic properties. Highly functionalized azulenes were enabled by cross-coupling reactions of even-numbered positions of azulenes. However, it has been difficult to synthesize these precursors.

Associate Professor Taku Shoji at Shinshu University et al. was successful in direct synthesis of 2-arylazulene. One of the few researchers who specialize in azulene synthesis, Professor Shoji states that the breakthrough in this study allows for the synthesis of azulene on a gram-scale instead of milligrams. The previous possible production volume made it difficult for possible use in organic electronics. Being able to synthesize azulenes from readily available 2H-cyclohepta[b]furan-2-one derivatives and silyl enol ether is a great step forward in practical applications.

The fluorescence of the azulene derivatives in acidic conditions (which can be seen in the photo) was observed unexpectedly during this study. Though this property of azulene derivatives had been previously reported, the research group found that 2-phenylazulenes exhibit the emission in acidic media and the fluorescence wavelength depends on the electronic properties of the substituents on the substituted benzene ring. The group is collaborating with photochemical experts to elucidate the mechanism of this unexpected fluorescence.

Professor Shoji and his team continue to attempt to synthesize 2-arylazulene at a lower temperature using an appropriate catalyst. Professor Shoji states that "although azulene have been studied for a hundred years, new synthetic methods, reactivity and physical properties continue to be discovered." He remains fascinated by what this mysterious blue substance can reveal and ultimately be applied for.
About Shinshu University:

Shinshu University is a national university in Japan and working on providing solutions for building a sustainable society through interdisciplinary research fields: material science (carbon, fiber, composites), biomedical science (for intractable diseases, preventive medicine), and mountain science. We aim to boost research and innovation capability through collaborative projects with distinguished researchers from the world. For more information please see:

Shinshu University

Related Organic Electronics Articles:

Printing organic transistors
Researchers successfully print and demonstrate organic transistors, electronic switches, which can operate close to their theoretical speed limits.
The ink of the future in printed electronics
A research group led by Simone Fabiano at the Laboratory of Organic Electronics, Linköping University, has created an organic material with superb conductivity that doesn't need to be doped.
Electronics at the speed of light
A European team of researchers including physicists from the University of Konstanz has found a way of transporting electrons at times below the femtosecond range by manipulating them with light.
Future of portable electronics -- Novel organic semiconductor with exciting properties
Organic semiconductors have advantages over inorganic semiconductors in several areas.
New synthesis method opens up possibilities for organic electronics
Scientists at Tokyo Institute of Technology (Tokyo Tech) modify a previous synthesis method to create a new semiconducting polymer with remarkable properties which could be used in organic electronic devices such as thin film transistors.
A new 'golden' age for electronics?
Scientists at Nagoya University, Japan, have created materials that shrink uniformly in all directions when heated under normal everyday conditions, using a cheap and industrially scalable process.
Organic electronics: a new semiconductor in the carbon-nitride family
Teams from Humboldt-Universität and the Helmholtz-Zentrum Berlin have explored a new material in the carbon-nitride family.
Verifying 'organic' foods
Organic foods are increasingly popular -- and pricey. Organic fruits and vegetables are grown without synthetic pesticides, and because of that, they are often perceived to be more healthful than those grown with these substances.
New way to beat the heat in electronics
Rice University researchers combine a polymer nanofiber layer with boron nitride to make a strong, foldable dielectric separator for high-temperature batteries and other applications.
Water creates traps in organic electronics
Poor-quality organic semiconductors can become high-quality semiconductors when manufactured in the correct way.
More Organic Electronics News and Organic Electronics Current Events

Trending Science News

Current Coronavirus (COVID-19) News

Top Science Podcasts

We have hand picked the top science podcasts of 2020.
Now Playing: TED Radio Hour

Listen Again: The Power Of Spaces
How do spaces shape the human experience? In what ways do our rooms, homes, and buildings give us meaning and purpose? This hour, TED speakers explore the power of the spaces we make and inhabit. Guests include architect Michael Murphy, musician David Byrne, artist Es Devlin, and architect Siamak Hariri.
Now Playing: Science for the People

#576 Science Communication in Creative Places
When you think of science communication, you might think of TED talks or museum talks or video talks, or... people giving lectures. It's a lot of people talking. But there's more to sci comm than that. This week host Bethany Brookshire talks to three people who have looked at science communication in places you might not expect it. We'll speak with Mauna Dasari, a graduate student at Notre Dame, about making mammals into a March Madness match. We'll talk with Sarah Garner, director of the Pathologists Assistant Program at Tulane University School of Medicine, who takes pathology instruction out of...
Now Playing: Radiolab

What If?
There's plenty of speculation about what Donald Trump might do in the wake of the election. Would he dispute the results if he loses? Would he simply refuse to leave office, or even try to use the military to maintain control? Last summer, Rosa Brooks got together a team of experts and political operatives from both sides of the aisle to ask a slightly different question. Rather than arguing about whether he'd do those things, they dug into what exactly would happen if he did. Part war game part choose your own adventure, Rosa's Transition Integrity Project doesn't give us any predictions, and it isn't a referendum on Trump. Instead, it's a deeply illuminating stress test on our laws, our institutions, and on the commitment to democracy written into the constitution. This episode was reported by Bethel Habte, with help from Tracie Hunte, and produced by Bethel Habte. Jeremy Bloom provided original music. Support Radiolab by becoming a member today at     You can read The Transition Integrity Project's report here.