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DOI: 10.1055/a-2560-0282
A Practical Synthesis of Multi-Site Functionalized Norbornadiene for Molecular Solar Thermal Energy Storage
The authors acknowledge funding from Göran Gustafssons Stiftelse för Naturvetenskaplig och Medicinsk Forskning, Vetenskapsrådet, and H2020 European Research Council (Grant: 'PHOTHERM'). DFT calculations were enabled by resources provided by Chalmers e-Commons.
Abstract
Norbornadienes (NBDs) are promising candidates for molecular solar thermal energy storage (MOST) due to their reversible photoisomerization. A central aspect for future application is the scalable synthesis of NBD derivatives with high solubility. Herein, we report an efficient synthesis and purification of multi-substituted NBDs, achieving diverse substitution patterns and appreciable solubility. The streamlined process for synthesizing and purifying NBDs delivers high yields and purity, which addresses previously significant challenges in NBD-based energy systems. Our findings advance sustainable approaches for MOST through improved NBD stability and usability.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2560-0282.
- Supporting Information
Publication History
Received: 14 January 2025
Accepted after revision: 24 February 2025
Accepted Manuscript online:
17 March 2025
Article published online:
12 June 2025
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1 Lewis NS, Nocera DG. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 15729
- 2 Bruce PG, Freunberger SA, Hardwick LJ, Tarascon J.-M. Nat. Mater. 2012; 11: 19
- 3 Bren VA, Dubonosov AD, Minkin VI, Chernoivanov VA. Russ. Chem. Rev. 1991; 60: 913
- 4 Quant M, Lennartson A, Dreos A, Kuisma M, Erhart P, Borjesson K, Moth-Poulsen K. Chemistry 2016; 22: 13265
- 5 Cristol SJ. Tetrahedron 1986; 42: 1617
- 6 Moth-Poulsen K, Ćoso D, Börjesson K, Vinokurov N, Meier SK, Majumdar A, Vollhardt KP. C, Segalman RA. Energy Environ. Sci. 2012; 5: 8534
- 7 Sun CL, Wang C, Boulatov R. ChemPhotoChem 2019; 3: 268
- 8 Magson L, Hölzel H, Aslam AS, Henninger S, Munz G, Moth-Poulsen K, Knaebbeler-Buss M, Funes-Ardoiz I, Sampedro D. ACS Appl. Mater. Interfaces 2024; 16: 7211
- 9 Borne KD, Cooper JC, Ashfold MN. R, Bachmann J, Bhattacharyya S, Boll R, Bonanomi M, Bosch M, Callegari C, Centurion M, Coreno M, Curchod BF. E, Danailov MB, Demidovich A, Di Fraia M, Erk B, Faccialà D, Feifel R, Forbes RJ. G, Hansen CS, Holland DM. P, Ingle RA, Lindh R, Ma L, McGhee HG, Muvva SB, Nunes JP. F, Odate A, Pathak S, Plekan O, Prince KC, Rebernik P, Rouzée A, Rudenko A, Simoncig A, Squibb RJ, Venkatachalam AS, Vozzi C, Weber PM, Kirrander A, Rolles D. Nat. Chem. 2024; 16: 499
- 10 Lorenz P, Hirsch A. Chem. Eur. J. 2020; 26: 5220
- 11 Zika W, Leng A, Weiß R, Pintér S, Schüßlbauer CM, Clark T, Hirsch A, Guldi DM. Chem. Sci. 2023; 14: 11096
- 12 Schulte R, Afflerbach S, Ihmels H. Eur. J. Org. Chem. 2023; 26: e202201398
- 13 Zähringer TJ. B, Perez Lopez N, Schulte R, Schmitz M, Ihmels H, Kerzig C. Angew. Chem. Int. Ed. 2025; 64: e202414733
- 14 Wang Z, Hölzel H, Moth-Poulsen K. Chem. Soc. Rev. 2022; 51: 7313
- 15 Börjesson K, Lennartson A, Moth-Poulsen K. ACS Sustainable Chem. Eng. 2013; 1: 585
- 16 Dreos A, Wang Z, Udmark J, Ström A, Erhart P, Börjesson K, Nielsen MB, Moth-Poulsen K. Adv. Energy Mater. 2018; 8: 1703401
- 17 Hemauer F, Steinrück H.-P, Papp C. ChemPhysChem 2024; 25: e202300806
- 18 Wang Z, Hölzel H, Fernandez L, Aslam AS, Baronas P, Orrego-Hernández J, Ghasemi S, Campoy-Quiles M, Moth-Poulsen K. Joule 2024; 8: 2607
- 19 Alex W, Lorenz P, Henkel C, Clark T, Hirsch A, Guldi DM. J. Am. Chem. Soc. 2022; 144: 153
- 20 Orrego-Hernández J, Hölzel H, Quant M, Wang Z, Moth-Poulsen K. Eur. J. Org. Chem. 2021; 5337
- 21 Ritter J. An Efficient Bounding Sphere . In Graphics Gems . Glassner AS. Academic Press; San Diego: 1990: 301-303
- 22 Liu P, Zhang Y, Wang H, Yip MK, Liu ES, Jin X. Computer Aided Geometric Design 2024; 111: 102305
- 23 Salthouse RJ, Moth-Poulsen K. J. Mater. Chem. A 2024; 12: 3180
- 24 Prat D, Wells A, Hayler J, Sneddon H, McElroy CR, Abou-Shehada S, Dunn PJ. Green Chem. 2016; 18: 288