ArticleBeilstein journal of organic chemistry2024
Extension of the π-system of monoaryl-substituted norbornadienes with acetylene bridges: influence on the photochemical conversion and storage of light energy.
Article in Beilstein journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Photoinduced Electron Transfer (PET) as Key to Accelerate the Cycloreversion Reaction of Arylquadricyclanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Get a better glimpse on sequential photoreactions of trisnorbornadienes withBeilstein journal of organic chemistry · 2026Article
- Harnessing light energy with molecules.Beilstein journal of organic chemistry · 2026Article
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6 authors.
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Abstract
The photochromic norbornadiene/quadricyclane pair is a promising system for molecular solar thermal (MOST) energy storage, with which solar energy may be converted, stored, and released as heat in one integral molecular system. Herein, we present the synthesis of mono-, bis-, and tris-norbornadiene derivatives with alkynylbenzene and alkynylnaphthalene core units, along with studies of their photochemical properties. The target compounds were synthesized by Sonogashira-Hagihara coupling reactions of 2-bromonorbornadiene and the corresponding arylacetylenes. The norbornadienes showed absorption maxima in the range of 310-345 nm and long-wavelength zero onsets of up to 420 nm. The photoisomerization quantum yields were as high as 59% per photoisomerization event and the resulting quadricyclanes showed half-lives of up to 8 h at room temperature. Furthermore, the norbornadienes were transformed quantitatively into their quadricyclane photoproducts by irradiation with green light (520 nm) in the presence of a photosensitizer.
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