Multicomponent Tandem Polymerization of Aromatic Alkynes, Carbonyl Chloride, and Fischer's Base toward Poly(diene merocyanine)s

Abstract

Summary of main observation and conclusion Multicomponent polymerization (MCP) is a popular tool to construct polymers with diverse structure, simple operation, and high efficiency, which faces the challenges of limited product structures. Multicomponent tandem polymerization (MCTP), combining two or multiple reactions in a one‐pot fashion, could expand the scope of MCP and enrich the polymer structures. Herein, a one‐pot three‐component tandem polymerization of diynes, carbonyl chloride, and Fischer's base has been developed to afford conjugated poly(diene merocyanine)s with mild condition, satisfactory molecular weights (Mw up to 10900 g/mol) and yields (up to 81%). The polymers enjoy good solubility and high thermal stability. The unique emission behavior of the model compound and polymer show that they are aggregation‐induced emission (AIE)‐active, suggesting that the diene merocyanine moiety is a potential AIEgen. This MCTP shows great potential in the preparation of functional polymer materials, which could build new AIE functional units directly from the polymerization, demonstrating its synthetic simplicity and elegance.

Advanced functional polymer materials

“…12, Route 5). 114 The MCTPs of N-(2-iodophenyl)-3-phenyl-N-tosylpropiolamide, aromatic terminal alkynes, and diamines were explored to afford poly(indolone)s with unique structures and high molecular weights (M w up to 30.4 Â 10 3 g mol À1 ) in high yields. 115 In addition, by combining Glaser coupling-nucleophilic additionheterocyclization-oxidation reactions, Hu and Tang et al reported the four-step MCTPs of diyne, guanidine hydrochloride, DMSO, and O 2 , affording conjugated poly(pyrimidine)s with well-defined and tunable structures.…”

Near‐Infrared Fluorescent Nanoprobe for Detecting Hydrogen Peroxide in Inflammation and Ischemic Kidney Injury

“…This feature is beneficial for fluorescence imaging in bio‐system. [ 28‐39 ] However, only a few organic probes have been developed for H 2 O 2 detection with AIE characteristic, and most of them still suffered from short wavelength emission (< 650 nm). [ 40‐44 ]…”

Multicomponent Polymerization for π‐Conjugated Polymers

“…[ 57,58 ] Moreover, when the active polyalkynone ( 4‐P15 ) was treated with Fischer's base as an enamine nucleophile, a π‐cross‐conjugated poly(diene merocyanine) ( 4‐P17 ) was generated via a consecutive addition‐cyclization‐ring opening pathway, as depicted in Figure 15b. [ 59,60 ]…”