轮环藤宁：从实验室到生命 Cyclen:From Laboratory to Life

Introduction

In the realm of chemistry, Cyclen (1,4,7,10-tetraazacyclododecane) and its derivatives have garnered significant attention from scientific researchers, attributed to their distinctive structural features and properties. Today, we delve into the intricacies of Cyclen, examining its synthesis, characteristics, and the myriad applications it holds within contemporary scientific and technological domains.

C8H20N4

Cyclen (1,4,7,10-tetraazacyclododecane) 

Synthesis of Cyclen

Since the 1960s, extensive research has been conducted on polyaza macrocyclic compounds. Among them, Cyclen (1,4,7,10-tetraazacyclododecane) and its derivatives have garnered considerable attention owing to their robust coordination capabilities with metal ions. Various methodologies exist for synthesizing Cyclen, including the Stetter synthesis, Richman-Atkins synthesis, Weisman synthesis, glyoxal condensation, and diethyl oxalate synthesis. In industrial production, the classic and high-yielding Richman-Atkins synthesis method is predominantly employed. This method utilizes diethylenetriamine and diethanolamine, proceeding through p-toluenesulfonylation, ring closure, deprotection, salt formation, alkalization, and finally isolation.

Properties of Cyclen

The Cyclen molecule possesses four imino groups, offering diverse opportunities for the preparation of various N-substituted derivatives. The four nitrogen atoms within the Cyclen ring are capable of forming stable complexes with metal ions, leading to their extensive utilization in various domains such as medicine, the development of enzyme mimics, metal cation extraction, and other advanced applications.

Applications of Cyclen

· Pharmaceutical field

One of the pivotal applications of Cyclen derivatives lies in the synthesis of various contrast agents that are indispensable for medical imaging. A notable example is Na[Gd(DOTA)(H2O)], where DOTA, a derivative of Cyclen, serves as a crucial component in MRI contrast agents.

· Catalysis and Molecular Recognition

Cyclen and its metal complexes have a wide range of uses in catalysis, molecular recognition, and as fluorescent probes, among other applications. By chemically modifying Cyclen, its functionality can be significantly enhanced, opening up further opportunities for scientific research and industrial applications.

· Solar Cells

Recent studies indicate that Cyclen molecules can enhance the performance of perovskite solar cells. Through the control of high-quality film production, Cyclen is able to diminish non-radiative recombination and prolong carrier lifetime, which in turn boosts the efficiency of the solar cells.

Cyclen Related Intermediates

Cyclen intermediates continue to captivate researchers due to their potent chelating capabilities for metal ions, resulting in complexes with a range of unique functions. Cyclen has applications in medicine, enzyme imitation, separation processes, and carrier gases, as well as in the extraction of metal cations. When Cyclen is appropriately modified, it can significantly enhance its coordination properties and the functionality of its complexes, making it a selective ligand for transition metals, heavy metals, lanthanides, and actinides in biomedical applications. Cyclen N, when attached to side chain groups like esters, amides, or pyridines, can act as a ligand for alkali metal cations, enabling the high-selectivity extraction of metal ions. Furthermore, Cyclen and its derivatives are instrumental in developing contrast agents and radioactive imaging agents for magnetic resonance imaging diagnostics in medicine, and their heavy metal complexes serve as X-ray contrast agents. Following crown ethers and cryptands, Cyclen and its derivatives represent another class of functional ligands with distinctive coordination characteristics. Their structural resemblance to chlorophyll, heme, and numerous biological enzymes allows their use in chemical simulation, molecular recognition, molecular magnets, and catalysts for biological and chemical reactions.

Conclusion

The research and application of Cyclen and its derivatives are constantly expanding, from the laboratory to life, their impact is everywhere. With the advancement of science and technology, we have reason to believe that Cyclen will play a more important role in future scientific research and industrial applications.

Let us look forward to more surprises and breakthroughs brought by Cyclen!

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