Perspectives on push-pull chromophores derived from click-type [2 + 2] cycloaddition-retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

Michio Yamada

doi:10.3762/bjoc.20.13

Perspectives on push-pull chromophores derived from click-type [2 + 2] cycloaddition-retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

Beilstein J Org Chem. 2024 Jan 22:20:125-154. doi: 10.3762/bjoc.20.13. eCollection 2024.

Author

Michio Yamada¹

Affiliation

¹ Department of Chemistry, Tokyo Gakugei University, Nukuikitamachi 4-1-1, Koganei, Tokyo 184-8501, Japan.

Abstract

Various push-pull chromophores can be synthesized in a single and atom-economical step through [2 + 2] cycloaddition-retroelectrocyclization (CA-RE) reactions involving diverse electron-rich alkynes and electron-deficient alkenes. In this review, a comprehensive investigation of the recent and noteworthy advancements in the research on push-pull chromophores prepared via the [2 + 2] CA-RE reaction is conducted. In particular, an overview of the physicochemical properties of the family of these compounds that have been investigated is provided to clarify their potential for future applications.

Keywords: click chemistry; donor–acceptor conjugate; intramolecular charge transfer; photoinduced electron transfer; photoluminescence.

Publication types

Review

Grants and funding

This work was supported by JSPS KAKENHI, Grant Numbers JP20K05472 and JP23K04704. It was also supported by the Shorai Foundation for Science and Technology.