Heteroaryl-linked norbornadiene dimers with redshifted absorptions
Journal article, 2018

Development of Molecular Solar Thermal (MOST) systems for harvesting and storing solar energy is based on molecular photoswitches that undergo photoisomerizations to metastable isomers. One challenge is to achieve low-molecular weight molecules that absorb at sufficiently long wavelengths to match the solar spectrum. Here we show that this can be achieved by linking two norbornadiene (NBD) photoswitches to a central heterocycle, thiophene or carbazole, via alkyne appendages. In this approach, the same heteroaryl is used to tune the properties of two photoswitches at the same time, thereby keeping the molecular weight as low as possible. A series of NBD dimers was prepared by Sonogashira coupling reactions, and these compounds showed remarkable redshifted absorptions, with onsets of absorption as high as 468 nm, and thermal half-lives ranging from 44 seconds to 16 hours.

Author

Mads Manso

University of Copenhagen

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Behabitu Ergette Tebikachew

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Kasper Moth-Poulsen

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Kasper Moth-Poulsen Group

M. B. Nielsen

University of Copenhagen

Organic and Biomolecular Chemistry

1477-0520 (ISSN) 1477-0539 (eISSN)

Vol. 16 31 5585-5590

Subject Categories

Atom and Molecular Physics and Optics

Theoretical Chemistry

Organic Chemistry

DOI

10.1039/c8ob01470a

More information

Latest update

8/20/2018