Flow-Integrated Preparation of Norbornadiene Precursors for Solar Thermal Energy Storage
Journal article, 2024

Molecular solar thermal (MOST) energy storage systems are getting increased attention related to renewable energy storage applications. Particularly, 2,3-difunctionalized norbornadiene-quadricyclane (NBD-QC) switches bearing a nitrile (CN) group as one of the two substituents are investigated as promising MOST candidates thanks to their high energy storage densities and their red-shifted absorbance. Moreover, such NBD systems can be prepared in large quantities (a requirement for MOST-device applications) in flow through Diels-Alder reaction between cyclopentadiene and appropriately functionalized propynenitriles. However, these acetylene precursors are traditionally prepared in batch from their corresponding acetophenones using reactive chemicals potentially leading to health and physical hazards, especially when working on a several-grams scale. Here, we develop a multistep flow-chemistry route to enhance the production of these crucial precursors. Furthermore, we assess the atom economy (AE) and the E-factor showing improved green metrics compared to classical batch methods. Our results pave the way for a complete flow synthesis of NBDs with a positive impact on green chemistry aspects.

Flow Chemistry

Norbornadiene

Propynenitrile

Multistep Reactions

Energy Storage

Author

Nicolò Baggi

Spanish National Research Council (CSIC)

Helen Hölzel

Polytechnic University of Catalonia

Hannes Schomaker

AutoSyn AB

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry

Kevin Moreno

Polytechnic University of Catalonia

Kasper Moth-Poulsen

Polytechnic University of Catalonia

Catalan Institution for Research and Advanced Studies

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry

Spanish National Research Council (CSIC)

ChemSusChem

1864-5631 (ISSN) 1864-564X (eISSN)

Vol. 17 2 e202301184

Subject Categories (SSIF 2011)

Physical Chemistry

Energy Engineering

Materials Chemistry

Organic Chemistry

DOI

10.1002/cssc.202301184

More information

Latest update

3/9/2025 1