SYNTHESIS OF PUSH–PULL CHROMOPHORES STARTING FROM NITROGEN-SUBSTITUTED ALKYNES

Date

2024-9-3

Author

İpek, Öktem

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Heterocyclic molecules are cyclic structures that contain at least one atom different from carbon atom, namely heteroatom, in a ring structure. Ynamine molecules can be synthesized using heterocycles and coupling them with terminal alkynes. These ynamine structures can be used as an electron-rich alkyne derivatives for [2+2] cycloaddition-retroeletrocyclization (CA-RE) reactions. [2+2] CA-RE represents reactions that happen between electron-rich alkynes and electron-deficient alkenes. Since the end-products can be purified easily, being high-yielding and atom-economic without the need of catalyst, these type of reactions are commonly called click-type of reactions and are used for the synthesis of conjugated molecules. TCNE, TCNQ, and DDQ are examples of electron-poor alkene derivatives that can be utilized for [2+2] CA-RE chemistry. One of the problems for these reactions is the limitation of electron rich alkyne derivatives. In this thesis, new ynamine derivatives will be synthesized as alternative substrates for [2+2] CA-RE with TCNE. The intramolecular cyclization of these new push-pull chromophores will also be investigated.

Subject Keywords

Heterocyclic chemistry, Ynamines, [2+2] Cycloaddition-retroeletrocyclization (CA-RE), Density functional theory, Transition state energy calculations

URI

https://hdl.handle.net/11511/111386

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Graduate School of Natural and Applied Sciences, Thesis