Synthesis, characterization and computational evaluation of bicyclooctadienes towards molecular solar thermal energy storage
Artikel i vetenskaplig tidskrift, 2022

Molecular solar-thermal energy storage (MOST) systems are based on photoswitches that reversibly convert solar energy into chemical energy. In this context, bicyclooctadienes (BODs) undergo a photoinduced transformation to the corresponding higher energy tetracyclooctanes (TCOs), but the photoswitch system has not until now been evaluated for MOST application, due to the short half-life of the TCO form and limited available synthetic methods. The BOD system degrades at higher temperature via a retro-Diels-Alder reaction, which complicates the synthesis of the compounds. We here report a cross-coupling reaction strategy that enables an efficient synthesis of a series of 4 new BOD compounds. We show that the BODs were able to switch to the corresponding tetracyclooctanes (TCOs) in a reversible way and can be cycled 645 times with only 0.01% degradation. Half-lives of the TCOs were measured, and we illustrate how the half-life could be engineered from seconds to minutes by molecular structure design. A density functional theory (DFT) based modelling framework was developed to access absorption spectra, thermal half-lives, and storage energies which were calculated to be 143-153 kJ mol(-1) (0.47-0.51 MJ kg(-1)), up to 76% higher than for the corresponding norbornadiene. The combined computational and experimental findings provide a reliable way of designing future BOD/TCO systems with tailored properties.

Författare

Maria Quant

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Andreas Erbs Hillers-Bendtsen

Köpenhamns universitet

Shima Ghasemi

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Mate Erdelyi

Uppsala universitet

Zhihang Wang

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Lidiya Musherefa Muhammad

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Nina Kann

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Kurt V. Mikkelsen

Köpenhamns universitet

Kasper Moth-Poulsen

Institut de Ciència de Materials de Barcelona (ICMAB-CSIC)

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Institucio Catalana de Recerca i Estudis Avancats

Chemical Science

2041-6520 (ISSN) 2041-6539 (eISSN)

Vol. 13 3 834-841

Drivkrafter

Hållbar utveckling

Ämneskategorier

Energiteknik

Teoretisk kemi

Organisk kemi

Styrkeområden

Energi

DOI

10.1039/d1sc05791j

Mer information

Senast uppdaterat

2022-03-23