Chemical Communications Blog

We are excited to share the success of Yuanting Su’s first-time independent article in ChemComm; ‘Crystalline radical cations of bis-BN-based analogues of Thiele’s hydrocarbon‘ included in the full milestones collection. 

Read our interview with Yuanting below.

What are the main areas of research in your lab and what motivated you to take this direction?

The main interests of our group are focused on the isolation, characterizations, and reactivity of novel main group species, including geometrically constrained compounds and di(poly)radicals. Recently, most of the stoichiometric and catalytic small molecule activations involve transition metal complexes. Additionally, organic radicals have potential applications in functional materials. We believe that main group species with suitable electronic and steric effects could also solve these problems and have their advantages.

Can you set this article in a wider context?

Thiele’s hydrocarbon, the first isolable organic diradicaloid reported by Thiele in 1904, has been widely used as a calculated model to investigate the interaction between two unpaired electrons. However, itself and its radical cation are highly reactive, preventing further investigation and practical application. Despite various analogues of Thiele’s hydrocarbon have been isolated, structurally characterized radical species derived from them are still limited and radical cations of bis-BN-based analogues have not been reported. In this paper, we demonstrate that air-stable bis-BN-based analogues of Thiele’s hydrocarbon have been facilely synthesized by one-pot reaction of bromoborane (HCDippN)₂BBr with KC₈ in the presence of half an equivalent of pyrazine or quinoxaline in toluene. Moreover, one-electron oxidation with AgSbF₆ leads to their radical cations, which could be isolated as crystalline solids. The unpaired electron is greatly delocalized over the central linkers. Therefore, reduction of the halogenated borane in the presence of pyrazine and derivatives is a straightforward way to achieve BN-based analogues of Thiele’s hydrocarbon with multiple stable redox states. This strategy may allow access to novel open-shell diradicaloids or polyradicals.

What do you hope your lab can achieve in the coming year?

Make progress in the construction of novel main group species for small molecule activation and functional materials.

Describe your journey to becoming an independent researcher.

When I was an undergraduate, my research experience with Prof. Suna Wang at Liaocheng University inspired me to pursue an academic research career. After graduation from the group of Prof. Xiao-Juan Yang and Prof. Biao Wu at Lanzhou Institute of Chemical Physics, where I learned a lot of knowledge and techniques on organometallics chemistry and characterizations, I joined the group of Prof. Xinping Wang at Nanjing University and studied the isolation of main group element radicals. Then, I was offered a Research Fellow position in Prof. Rei Kinjo’s group at Nanyang Technological University, where I expanded my research area into the small molecule activations by novel main group element species. I was fortunate to meet such kind and professional chemists, whose strong support helped me to become an independent researcher.

What is the best piece of advice you have ever been give?

You can neither rewrite your past nor predict your future. The best thing you can do is holding the present.

Why did you choose to publish in ChemComm?

ChemComm combines the traits of wide readership, rapid publishing, and high quality.

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Yuanting Su received his BSc Degree from Liaocheng University in 2009. Then, he moved to Lanzhou Institute of Chemical Physics, CAS and obtained his MSc Degree in 2012 under the guidance of Prof. Xiao-Juan Yang and Prof. Biao Wu. He earned his PhD in 2015 from Nanjing University under the supervision of Prof. Xinping Wang, studying the isolation of main group element radical species. He stayed as a Research Fellow at Prof. Rei Kinjo’s group at Nanyang Technological University (Sep. 2015 to Sep. 2019), Singapore, focusing on small molecule activation by main group element compounds. In Nov. 2019, he joined the College of Chemistry, Chemical Engineering and Materials Science, Soochow University as an Associate Professor. His current research interests are new main group species and their applications in small molecule activation and functional materials.

Explore more ChemComm Milestones news and updates on our Twitter: @ChemCommun

We are excited to share the success of Bin Wang’s first-time independent article in ChemComm; ‘tert-Butyl nitrite triggered radical cascade reaction for synthesizing isoxazoles by a one-pot multicomponent strategy‘ included in the full milestones collection. 

Read our interview with Bin below.

What are the main areas of research in your lab and what motivated you to take this direction?

Our laboratory currently focuses on the glycosylation reaction of nitrogen-containing heterocycles to acquire drug-like molecules. Many bioactive components in traditional Chinese medicine (TCM) contain glycosyl groups, which increase the water solubility of these molecules. According to the decoction method used in TCM, these compounds are more likely to be the active components of TCM. Additionally, in the development of synthetic drugs, glycosyl groups are often introduced into poorly soluble lead compounds to increase their hydrophilicity, improve the bioavailability of the target drugs, and finally increase the potential druggability.

Can you set this article in a wider context?

As early as 1888, the synthesis of isoxazole derivatives was first documented through the condensation/cyclization reaction of 1,3-dicarbonyl compounds with hydroxylamine by Claisen. Subsequently, two typical strategies for the synthesis of isoxazoles involve 1,3-dipolar cycloaddition of nitrile oxides; and alkynes and cyclo-isomerization of alkynyl ketoxime compounds.

In this article, we describe a novel and efficient multicomponent cascade reaction that involves sequential acylation/oximation/annulation processes in the presence of alkenes, aldehydes, TBN, and H₂O, providing access to diversely disubstituted isoxazoles in one-pot. This strategy features H₂O as a rare oxygen source of the isoxazole ring, commercially available substrates, and the construction of diverse new bonds in a single pot, which is distinct from already reported studies. These characteristics meet exactly the needs of environmental protection.

Additionally, we applied the established method to provide 32 isoxazole derivatives, and antioxidant experiments showed that these compounds have positive radical scavenging capacity, especially isoxazole 4al reaching 60% scavenging power at a concentration of 2 μmol/mL, suggesting that these molecules could be utilized as lead compounds for anti-aging drugs.

What do you hope your lab can achieve in the coming year?

In the next year, we will focus on carbohydrate chemistry, especially around the glycosylation reaction to achieve the synthesis of antioxidant and/or anti-inflammatory substances.

Describe your journey to becoming an independent researcher.

After completing my master’s degree in physical chemistry (Hunan University, China), I pursued a Ph.D. in organic chemistry for synthesis methodology to explore the functionalization of alkenes or alkynes in the aqueous phase. (University of Science and Technology of China, China), followed by an Associate Professor position focused on the synthesis of nitrogen-containing heterocycles to acquire drug-like molecules (Anhui University of Chinese Medicine, China). Subsequently, I accepted a visiting scholar position from the Georg-August-University of Goettingen, working on glycosylation reactions. Currently, my research group consists of 1 Ph.D. student, 7 masters, and 9 undergraduates. Inspired by the experiences described above and with an interest in exploring TCMs, I begin my independent career to navigate new fields between nitrogen-containing heterocycles and carbohydrate chemistry.

What is the best piece of advice you have ever been give?

“Do important and useful chemistry”. Innovation and practicality could go hand in hand. The application of chemical synthesis to solve problems in social life is more in agreement with the needs of human development, for instance, the total synthesis of natural products, synthesizing drug molecules, etc. Therefore, in the course of my academic research, this word has been guiding and inspiring me.

Why did you choose to publish in ChemComm?

ChemComm is a highly readable journal. The novelty of the published paper and the rapid publication process attracted me deeply to publish my first research article.

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Dr. Bin Wang completed his Ph.D. at the University of Science and Technology of China working with Prof. Zhiyong Wang, where he explored the functionalization of alkenes or alkynes in the aqueous phase. In 2021, he accepted a visiting scholar position in the group of Prof. Dr. Lutz Ackermann at the Georg-August University of Goettingen, working on synthetic methodology. Currently, he holds the position of Associate Professor position at the Key Laboratory of Xin’an Medicine of the Ministry of Education of the Anhui University of Chinese Medicine. His research is focused on the application of glycosylation to acquire drug-like molecules.

Explore more ChemComm Milestones news and updates on our Twitter: @ChemCommun

We are excited to share the success of Philip Norcott’s first-time independent article in ChemComm; ‘Current electrochemical approaches to selective deuteration‘ included in the full milestones collection. 

Read our interview with Philip

What are the main areas of research in your lab and what motivated you to take this direction?

I am interested in finding simple ways to synthesise new molecules that are designed for particular purposes or show unusual chemical properties. One of these synthetic methods is electrochemistry – using electrical potential to drive oxidation or reduction reactions instead of chemical reagents. An outcome of synthesis where I’m focused is in field of NMR hyperpolarisation, which is a technique to increase signal levels and detect trace intermediates or other compounds. In NMR studies, deuteration can be very important, but making deceptively simple deuterated molecules comes with its own synthetic challenges. 

Can you set this article in a wider context?

Electrosynthesis is becoming far more accessible as a synthetic technique, even for self-described ‘non-experts.’ Part of the attraction of this method is the potential to produce valuable molecules in a more efficient, safer, milder, and controllable way. In the context of deuteration, instead of using deuterium gas under forcing conditions or very expensive analogues of deuterated synthetic reagents, electrochemistry opens up access to a wide range of reactive intermediates which can readily acquire deuterium from simple, cheap sources. Often, and ideally, this can simply be D2O. This article identifies the current strategies and substrates able to undergo selective deuteration in this way, and suggests areas where the burgeoning interest in electrochemistry currently in the synthetic community can play a part to develop further labelling processes.

What do you hope your lab can achieve in the coming year?

I hope to be able to demonstrate reactions which display interesting chemoselectivity enabled by electrochemistry, and a new process for hyperpolarising organic compounds.

Describe your journey to becoming an independent researcher.

I did my PhD in organic chemistry at the University of Sydney, Australia, then went on to do two postdocs at the University of York, United Kingdom, then the Australian National University in Canberra, Australia. Working on very different projects in each provided me with an opportunity to try out some new areas of chemistry, and these topics ended up laying the groundwork for my current research interests. I was awarded an Australian Research Council Discovery Early Career Researcher Award (ARC DECRA) in 2021 to begin my independent research career.

What is the best piece of advice you have ever been give?

When reading articles or attending conference presentations and seminars, try to identify at least one part you don’t understand: a reaction, chemical reagent, word or concept that’s new to you, and take it as a chance to broaden your knowledge.

Why did you choose to publish in ChemComm?

ChemComm is renowned for quality and timely research in all of chemistry, and so appeals to a wide audience in terms of readers’ fields, backgrounds and interests; by submitting to ChemComm I hoped to engage as broad an audience as possible with my article topic.

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Philip L. Norcott completed his PhD at the University of Sydney, Australia, in 2016 with a focus on organic synthesis using catalysis in aqueous emulsions. He then spent two years as a postdoctoral researcher at the University of York, United Kingdom, at the Centre for Hyperpolarisation in Magnetic Resonance, with an emphasis on the synthesis of isotopically labelled materials for NMR applications. Following this he returned to Australia as a postdoctoral researcher at the Australian National University in Canberra, investigating the application of electrochemistry and electrostatic effects on organic chemical reactivity. He was awarded an Australian Research Council Discovery Early Career Researcher Award (ARC DECRA) in 2021 to launch a research program which is focused on synthetic methods to improve NMR hyperpolarisation through activation of para-hydrogen, and the synthesis of isotopically labelled molecules enabled by electrochemistry.

Explore more ChemComm Milestones news and updates on our Twitter: @ChemCommun