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Updated: Apr 29, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Making nonsymmetrical bricks: synthesis of insoluble dipolar sexiphenyls
Yves Garmshausen1, Jutta Schwarz, Jana Hildebrandt
1Department of Chemistry & IRIS Adlershof, Humboldt-Universität zu Berlin , Brook-Taylor-Strasse 2, 12489 Berlin, Germany.
Abstract:
A versatile synthesis of nonsymmetrical, terminally substituted p-sexiphenyl (6P) derivatives has been developed. The synthesis makes use of a nonsymmetrical starting material as well as modular functionalization using Suzuki cross-coupling to yield a soluble precursor, which finally is converted to the insoluble target 6P derivatives. These derivatives display similar electronic and optical properties to the parent 6P, yet the permanent dipole along their molecular axis allows for tuning of their self-assembly on various substrate surfaces.
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