The [2+2] Cycloaddition-Retroelectrocyclization (CA-RE) Click Reaction: Facile Access to Molecular and Polymeric Push-Pull Chromophores

Angewandte Chemie
Tsuyoshi Michinobu, François Diederich

Abstract

The [2+2] cycloaddition-retroelectrocyclization (CA-RE) reaction between electron-rich alkynes and electron-deficient alkenes is an efficient procedure to create nonplanar donor-acceptor (D-A) chromophores in both molecular and polymeric platforms. They feature attractive properties including intramolecular charge-transfer (ICT) bands, nonlinear optical properties, and redox activities for use in next-generation electronic and optoelectronic devices. This Review summarizes the development of the CA-RE reaction, starting from the initial reports with organometallic compounds to the extension to purely organic systems. The structural requirements for rapid, high-yielding transformations with true click chemistry character are illustrated by examples that include the broad alkyne and alkene substitution modes. The CA-RE click reaction has been successfully applied to polymer synthesis, with the resulting polymeric push-pull chromophores finding many interesting applications.

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Citations

Oct 17, 2018·Angewandte Chemie·Tobias A SchaubRamesh Jasti
Feb 28, 2020·Chemical Communications : Chem Comm·Anh Thy BuiYann Trolez
Feb 9, 2019·Scientific Reports·A MilaniC S Casari
Apr 4, 2019·International Journal of Molecular Sciences·Pedada Srinivasa RaoSheshanath V Bhosale
Apr 29, 2021·Angewandte Chemie·Carlo ThilgenThomas Carell
Mar 9, 2019·The Journal of Organic Chemistry·Yago García-Rodeja, Israel Fernández
Sep 11, 2020·The Journal of Organic Chemistry·Mariusz TasiorDaniel T Gryko
Jun 27, 2019·The Journal of Organic Chemistry·Arif Hassan DarGovindasamy Jayamurugan
Jun 30, 2019·The Journal of Organic Chemistry·Shaista SultanBhahwal Ali Shah
Mar 29, 2020·ACS Applied Materials & Interfaces·Shengxian ChengZhengtao Xu
Mar 5, 2020·The Journal of Organic Chemistry·Yogajivan RoutRajneesh Misra
Sep 30, 2021·Physical Chemistry Chemical Physics : PCCP·Nicolas RipocheFrédéric Paul
Nov 17, 2021·The Journal of Organic Chemistry·Alexander A FadeevMaxim G Uchuskin
Dec 30, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Arif Hassan DarGovindasamy Jayamurugan

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