Geminal Cross-Coupling of 1,1-Dibromoolefins Facilitating Multiple Topological π‑Conjugated Tetraarylethenes

• Published in: Macromolecules 2015-11, Vol.48 (21), p.7823-7835
• Main Authors: Chen, Ze-Qiang, Chen, Tao, Liu, Jun-Xia, Zhang, Guo-Feng, Li, Chong, Gong, Wen-Liang, Xiong, Zu-Jing, Xie, Nuo-Hua, Tang, Ben Zhong, Zhu, Ming-Qiang
• Format: Article
• Language: English
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/acs.macromol.5b01602

The cross-coupling reactions have been used in C–C bond formation which can be used extensively in optoelectronic materials for organic light-emitting diodes, organic photovoltaics, and chemical biosensing. Here, we report 2-fold geminal C–C bond formation at 1,1-dibromoolefins via cross-coupling reactions of aromatic boronic esters over Pd catalysts for multiple topological configurations of π-conjugated molecules. We employ a series of recipes from a precursor toolbox to produce π-conjugated macrocycles, conjugated dendrimers, linear conjugated polymers, and multiple conjugated microporous polymers and nanoparticles. The π-conjugated macrocycles, dendrimers, and linear polymers show characteristic aggregation-induced emission properties. The conjugated microporous polymers possess unique porosity of 2–3 nm. The microporous polymer nanoparticles can be redispersed in solution. This universal strategy toward definite topological configurations of π-conjugated molecules enables efficient coupling of aryl bromides with various coupling partners under mild conditions affording multiple topological conjugated systems with abundant optical and optoelectronic interest.