Multicomponent Spiropolymerization of Diisocyanides, Diethyl Acetylenedicarboxylate, and Halogenated Quinones

Abstract Multicomponent spiropolymerization (MCSP) provides an efficient synthetic tool for the construction of spiropolymers based on nonspiro monomers. In this study, a method of MCSP using diisocyanides 1 , diethyl acetylenedicarboxylate 2 , and halogenated quinones 3 is developed for the in situ construction of bis‐spiropolymers with high molecular weights ( M w up to 29 200) and good yields (up to 87.7%) under mild reaction conditions. The structure of the obtained bis‐spiropolymers is confirmed by gel permeation chromatography, Fourier transform infrared spectroscopy, and nuclear magnetic resonance analysis. Halogenated bis‐spiropolymers show good thermal stability, good solubility, and film‐forming ability. The photosensitizer rhodamine B is used as a doping agent to induce the photodegradation of the polymer P1a3c into small‐molecule segments, which results in the slow release of halogenated spiro‐groups under irradiation with simulated sunlight. This finding reveals that P1a3c has the potential to be applied in pesticides. Therefore, this MCSP is a novel method for preparing halogen‐containing bis‐spiropolymers, which accelerates the development of multifunctional polymer materials.