AI Article Synopsis
- Researchers have developed a method to create single-handed helicene nanoribbons using [6]helicene building blocks to trigger the formation of [5]helicene units through a selective photochemical process.
- The synthesized nanoribbons, containing about 50-60 annulated benzene rings, represent the longest optically active helicene structures made so far.
- The study shows that chiroptic properties of these nanoribbons demonstrate how stereochemical information is transferred from the [6]helicene units ("sergeants") to the [5]helicene units ("soldiers"), and similar designs in model oligomers confirm a preference for homochiral configurations.
Article Abstract
Here we show the access to single-handed helicene nanoribbons by utilizing a [6]helicene building block to induce diastereoselective, photochemical formation of [5]helicene units. Specifically, we have synthesized nanoribbons and with different ratios of [6]helicene "sergeants" to [5]helicene "soldiers", which on average consist of between ∼50 and 60 -annulated benzene rings. These are the longest, optically active helicene backbones that have been prepared to date. The chiroptic properties of and reveal the transfer of stereochemical information from "sergeants" to "soldiers". To gain further insight into the stereo-information relay, we apply the same molecular design to discrete, model oligomers - and confirm that they also preferentially adopt homochiral geometries.
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| http://dx.doi.org/10.1021/jacs.2c09288 | DOI Listing |
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Article Synopsis
- Researchers have developed a method to create single-handed helicene nanoribbons using [6]helicene building blocks to trigger the formation of [5]helicene units through a selective photochemical process.
- The synthesized nanoribbons, containing about 50-60 annulated benzene rings, represent the longest optically active helicene structures made so far.
- The study shows that chiroptic properties of these nanoribbons demonstrate how stereochemical information is transferred from the [6]helicene units ("sergeants") to the [5]helicene units ("soldiers"), and similar designs in model oligomers confirm a preference for homochiral configurations.
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