Norbornadiene-Quadricyclane Photoswitches with Enhanced Solar Spectrum Match
Journal article, 2024

Herein, we report monomeric and dimeric norbornadiene-quadricyclane molecular photoswitch systems intended for molecular solar thermal applications. A series of six new norbornadiene derivatives conjugated with benzothiadiazole as the acceptor unit and dithiafulvene as the donor unit were synthesized and fully characterized. The photoswitches were evaluated by experimentally and theoretically measuring optical absorption profiles and thermal conversion of quadricyclane to norbornadiene. Computational insight by density functional theory calculations at the M06-2X/def2-SVPD level of theory provided geometries, storage energies, UV-vis absorption spectra, and HOMO-LUMO levels that are used to describe the function of the molecular systems. The studied molecules exhibit absorption onset ranging from 416 nm to 595 nm due to a systemic change in their donor-acceptor character. This approach was advantageous due to the introduction of benzothiadiazole and the dimeric nature of molecular structures. The best-performing system has a half-life of 3 days with quantum yields over 50 %.

Photoswitches

Dithiafulvene

Benzothiadiazole

Redshift

Norbornadiene

Author

Muhammad Adil Salman Aslam

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry

Lidiya Musherefa Muhammad

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry

Andreas Erbs Hillers-Bendtsen

University of Copenhagen

Kurt V. Mikkelsen

University of Copenhagen

Kasper Moth-Poulsen

Institute of Material Science of Barcelona (ICMAB)

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry

Polytechnic University of Catalonia

Catalan Institution for Research and Advanced Studies

Chemistry - A European Journal

0947-6539 (ISSN) 1521-3765 (eISSN)

Vol. 30 46 e202401430

Molecular Solar Thermal energy storage systems (MOST)

European Commission (EC) (EC/H2020/951801), 2020-09-01 -- 2024-02-29.

Swedish Energy Agency (2019-010724), 2019-05-07 -- 2019-09-03.

Subject Categories

Atom and Molecular Physics and Optics

Other Physics Topics

Theoretical Chemistry

Organic Chemistry

DOI

10.1002/chem.202401430

More information

Latest update

9/5/2024 7