Scalable Synthesis of Norbornadienes via in situ Cracking of Dicyclopentadiene Using Continuous Flow Chemistry
Artikel i vetenskaplig tidskrift, 2021

The norbornadiene (NBD)-quadricyclane (QC) photoswitch has recently attracted attention due to its use in molecular solar thermal energy systems (MOST). Normally for device testing, several grams are needed. One way of synthesizing NBDs efficiently is through the Diels-Alder reaction between alkynes and cyclopentadiene. However, scaling up the reaction can be troublesome in a research lab environment. Also, dicyclopentadiene needs cracking before utilization which is a time-consuming step. Here, we developed a method where we both scale up the synthesis in a single reaction step that involves both in situ cracking of dicyclopentadiene and the direct reaction of cyclopentadiene with acetylene derivatives using a tubular coiled stainless steel flow reactor. As a proof-of-concept, we synthesized six different NBD compounds and scaled the synthesis to produce 87 g of a novel NBD in 9 h. The NBD is further characterized, showing promising properties for MOST applications. Our new method shows that flow chemistry is an attractive technique for the fast and efficient synthesis of large quantities of NBDs, needed to develop future real-life devices and applications.



Energy storage

Flow chemistry



Jessica Orrego Hernandez

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Helen Hölzel

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Maria Quant

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Zhihang Wang

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Kasper Moth-Poulsen

Chalmers, Kemi och kemiteknik, Tillämpad kemi

European Journal of Organic Chemistry

1434-193X (ISSN) 10990690 (eISSN)

Vol. 2021 38 5337-5342




Organisk kemi



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