Tandem Suzuki Polymerization/Heck Cyclization Reaction to Form Ladder-Type 9,9′-Bifluorenylidene-Based Conjugated Polymer

Abstract

The synthesis of ladder-type 9,9′-bifluorenylidene-based conjugated polymer is reported. Unlike the typical synthetic strategy, the new designed ladder-type conjugated polymer is achieved via tandem Suzuki polymerization/Heck cyclization reaction in one-pot. In the preparation process, Suzuki polymerization reaction occurred first and then the intramolecular Heck cyclization followed smoothly under the same catalyst Pd(PPh3)4. The model reaction proved that the introduction of iodine (I) for this tandem reaction can effectively control the sequential bond-forming process and inhibit the additional competitive side reactions. Thus, small-molecule model compounds could be obtained in high yields. The successes of the synthesized small molecule and polymer compounds indicate that the Pd-catalyzed tandem reaction may be an effective strategy for improving extended π-conjugated materials.

Keywords

• 9,9′-bifluorenylidene
• ladder type conjugated polymer
• tandem reaction
• Suzuki polymerization
• Heck cyclization