Controlling helicene's pitch by molecular tethering

We applied post-cyclization annulation to introduce a series of tethered S-shaped double [4]helicenes in which the intramolecular tether imposes a specific helical handedness. Introducing a tether and then shortening the tether length incrementally increase the pitch angle of [4]helicene, thus enabl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-02, Vol.22 (7), p.1365-1368
Main Authors: Agrawal, Abhijeet R, Shiouki, Israa, Deree, Yinon, Bogoslavsky, Benny, Gidron, Ori
Format: Article
Language:English
Subjects:
Chemical reactions
Handedness
Optical properties
Pitch (inclination)
Quantitative research
Tethering
Tethers
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Summary:We applied post-cyclization annulation to introduce a series of tethered S-shaped double [4]helicenes in which the intramolecular tether imposes a specific helical handedness. Introducing a tether and then shortening the tether length incrementally increase the pitch angle of [4]helicene, thus enabling a quantitative study of the effects of helicene's pitch on its electronic and (chiro)optical properties. We applied post-cyclization annulation to introduce a series of tethered S-shaped double [4]helicenes in which the intramolecular tether imposes a specific helical handedness, while the tether length determines the helicene's pitch.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob02075d