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

被引：136

作者：

Michinobu, Tsuyoshi ^{[1
]}

Diederich, Francois ^{[2
]}

机构：

[1] Tokyo Inst Technol, Dept Mat Sci & Engn, Meguro Ku, 2-12-1 Ookayama, Tokyo 1528552, Japan

[2] ETH, Lab Organ Chem, Vladimir Prelog Weg 3, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 14期

基金：

瑞士国家科学基金会;

关键词：

click chemistry; cycloaddition-retroelectrocyclization cascade; optoelectronics; polymers; push-pull chromophores; DONOR-ACCEPTOR CHROMOPHORES; CHARGE-TRANSFER INTERACTIONS; NONLINEAR-OPTICAL PROPERTIES; ONE-STEP SYNTHESIS; CHEMISTRY-TYPE POSTFUNCTIONALIZATION; SINGLET-EXCITON-FISSION; ENERGY-LEVEL MODULATION; ELECTRON-RICH ALKYNES; SLOT WAVE-GUIDES; HOMO-LUMO GAP;

D O I：

10.1002/anie.201711605

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：3552 / 3577

页数：26

共 311 条

[21] REACTIONS OF TRANSITION-METAL SIGMA-ACETYLIDE COMPLEXES .10. CYCLOADDITION OF TETRACYANOETHENE TO MANGANESE, IRON AND NICKEL-COMPLEXES, AND HYDRATION OF A RELATED TUNGSTEN COMPLEX - X-RAY STRUCTURES OF FE(C[=C(CN)2]CPH=C(CN)2)(CO)2(ETA-C5H5) AND NI(C[=C(CN)2]CPH=C(CN)2)(PPH3)(ETA-C5H5) [J].